Missy Elliott’s debut album Supa Dupa Fly was released on July 15, 1997, and remains in the multiple GRAMMY-winning artist’s heavy listening rotation. Her forward-thinking gift for writing, rapping and singing memorable songs with gospel-informed soul hooks and time signature-shattering beats ushered in the 2000s early and sent everyone scrambling to copy the new style.

"A lot of times, when I need some inspiration now, I listen to it," Elliott tells GRAMMY.com in a rare interview. "To be honest, I listen to it because I feel like we were in such a vulnerable place and we didn’t have any kind of expectations, so we just did what felt good to us."

The "we" is Elliott and her friend Tim "Timbaland" Mosley, who served as her co-executive producer and close musical collaborator on Supa Dupa Fly. Together, they served up a perfectly arranged, cohesive collection of songs and interludes that still shows artists around the world how to think outside the box musically. They not only influenced hip-hop and R&B acts, but Southern chopped and screwed DJs, house music producers, drum & bass experimentalists, and much more.

"So I always try to go back to that space," Elliott says, "because once you become successful at something then the expectations become higher and you start to think more. When we did that album, there wasn’t really much thought there …. We really just came out with a sound that we had been doing for some time, but we had no clue that it would be game changing, that we would change the cadence — the sound of what was happening at that time. No clue!"

Remarkably, this hit album — which generated four singles and compelling music videos for "The Rain (Supa Dupa Fly)," "Sock It To Me," "Beep Me 911" and "Hit Em Wit Da Hee" — was written and recorded in days, and was nominated for Best Rap Album and Best Rap Solo Performance at the 40th GRAMMY Awards.

"There have been times I’ve had ideas ahead," she shares, "but for this particular album, it was most definitely right on the spot. It took us two weeks to record this album and it was because, at the time, I didn’t want to be an artist."

Elliott had just been in an R&B group called Sista that was signed to Elektra Entertainment Group under a record label headed up by Jodeci founder and producer DeVante Swing. Sista recorded an album, but it wasn’t released after Swing parted ways with Elektra.

The stalled experience made Elliott want to focus on songwriting and developing other artists instead of being in the spotlight. Ultimately, she inked  a business deal with Elektra executive Sylvia Rhone that included a solo recording contract as well as her own record label.

"A lot of people wanted to sign me; there was a bidding war," Elliott explains. "Every label out there was trying to get me to sign to them and I wanted to have a record label instead of being an artist. When I took a meeting with Sylvia Rhone about having a record label she said, ‘I’ll give you a label if you give me an album.’ So we went in and I was like, ‘Tim, let’s go in here and do this album real quick so I can get started on my label.’"

Rhone gave Elliott no guidance other than to just be herself in the studio, and she deferred to Elliott’s artistic decisions — a record business rarity both then and now. 

"She had an eye," Elliott says of Rhone. "She is a creator, a visionary, so she saw it." Just two months after it was released, Supa Dupa Fly brought Elliott’s new record label The Goldmind, Inc. its first certified Platinum album.

The album’s lead single "The Rain (Supa Dupa Fly)" and the unforgettable accompanying video were released two months before the album dropped, and undoubtedly helped to propel album sales. Most of the album isn’t built around samples, but "The Rain" features a hook created by sampling a song that came out in 1973, when Elliott was just 2 years old: Ann Peebles’ "I Can’t Stand The Rain."

Peebles’ song features sounds that evoke water droplets, which were created by overdubbing notes played on an electric timbale, then a new instrument on the scene. "I Can’t Stand The Rain" was later covered by a disco group called Eruption, who took it to No. 1 in Belgium and Australia in 1978, and Tina Turner, who included it on her 1984 smash album Private Dancer.

"Ann Peebles is iconic," Elliott says. "That sample in itself was a big contributor to that record. I got a chance to take a picture and meet her, and of course she loved it and I love her. Even when you listen to the original version, there is a nostalgia about it. And that’s what made us gravitate to that record anyway, because it had a hypnotic feel to it.

"I don’t know where Ann Peebles lives, so I wouldn't say we go to Six Flags every other weekend," Elliott says when asked if the two stay in touch. "But she was most definitely so sweet when I met her and I am humbly grateful that she allowed us to use that record. I’m quite sure that if we ran into each other again there would always be love — and shoot, if she wanted to go to Six Flags, we could go to Six Flags! She is very, very sweet."

The album features some significant guest stars, including the late star Aaliyah, a beloved protege of Timbaland’s and Elliott’s, who duets on "Best Friends"; Ginuwine, the singer of "Pony" fame; and rap star Busta Rhymes, then an Elektra labelmate at the time. There are also appearances by singer Nicole Wray, the first artist signed to Goldmind; and Magoo, a rapper and friend from Elliott's Virginia hometown Virginia friend of the executive producers.

Elliott recognizes the staying power of the song and the imagery she created in the video for "The Rain." Her inflated and oversized black suit, which brilliantly pokes fun at beauty standards, is regularly and lovingly parodied by fans in YouTube and TikTok videos.

"'The Rain' was such nostalgia, I think about it a lot," Elliott reflects. "When I see pictures, it’s like the beginning of such a legacy. I just posted something the other day — people are still grabbing Glad trash bags, mimicking that video."

"The Rain" video is so enduring, that it’s worth reminding that three other incredible videos came from Supa Dupa Fly. Elliott (in a space suit emblazoned with the Gmail logo) and Da Brat orbit outer space in a high-tech anime fantasy filmed for "Sock It To Me." She’s a technicolor princess in "Beep Me 911" (which features the Las Vegas R&B group 702), and effortlessly channels Michael Jackson’s "Smooth Criminal" era in "Hit Em Wit Da Hee," a collaboration with Lil’ Kim.

"Yeah, I was everywhere!" Elliott says of those groundbreaking and large-scale videos, which came with six-figure price tags. "That’s the fun thing about it: I feel like I came up in the era of experimenting. The '80s were really experimental. The '90s were really the piggyback off of that, so it allowed the '90s artists to be experimental. That’s the greatness about the videos that I did: they take you on a ride. You feel like you’re in those places in each video."

Supa Dupa Fly and those accompanying music videos earned Elliott some very big fans.

"Janet [Jackson], Whitney [Houston] — so many of those legends, I was like, ‘Wow, did I arrive?’" Elliott remembers. "I remember I had Whitney sing on the phone because I couldn’t believe it was her. You just didn't get a call from Janet and Mike [Jackson] … so I answered the phone and she was like, [uses quiet voice] ‘Hi, it’s Janet,’ and I’m like, ‘Stop playing on my phone!’ I’m thinking it’s one of my friends and I hung up and then my manager called me and said, ‘Hey, Janet is going to be calling you.’ I’m like, ‘Oh my God, why didn't you tell me? I just hung up on her!’ So people like that most definitely enjoyed the album."

The success of Supa Dupa Fly was additionally resonant for Elliott, who had wanted to be behind the scene. 

"I felt like months before, I didn’t want to be an artist and now I’m rethinking it because I was like, ‘Wow, this is fun! Y’all really like it?’" Elliott remembers. "[Supa Dupa Fly] allowed me to work with a lot of different artists and the thing was, they appreciated the fresh new sound that hadn’t been heard."

"Missy always wanted to be up there," her mother confessed to the New Yorker in 1997. "As a little girl, she would ask me to bring home stamps, for all these letters she was writing. The letters would be returned, and I’d see that she’d written to Diana Ross, and whatnot."

25 years on, Elliott — firmly up there — hopes to celebrate this special Silver anniversary of Supa Dupa Fly in a major way.

"I think I’m going to have a big party and just celebrate, because it is a big mark in my career," she says. "That was the beginning and I do remember it like it was yesterday; I do remember going in the studio and not knowing. I didn't think about what 25 years would look like; I was living in the moment. Now, I feel like it’s time.

"In 2022, I’m able to reminisce and enjoy that space," she adds. "I feel like that a lot of times. There were a lot of big moments in my career — we didn’t come up in the social media world, we didn’t start that way, so a lot of it was just living in the moment. Now, I get a chance to look back and appreciate it and be like, 'Wow, that was a game changing time,' enjoy it and smell the flowers."

RZA’s Constant Elevation: From Wu-Tang to 'Kill Bill,' The Rapper/Producer Discusses His Creative Process And History Ahead Of Bobby Digital Reprise

At its core, hip-hop began as a joyful expression, a grassroots community-organizing method, and an outlet to creatively and freely rebel against the socioeconomic turmoil happening across America in the early '70s. The genre's mythical-like origin remains an integral part of American history: From the recreation room of 1520 Sedgwick Avenue, an 18-story apartment building in the South Bronx, New York City, DJ Kool Herc captivated audiences young and old as he commanded the turntables at a birthday party for his sister, Cindy Campbell, while MCs Theodore Puccio and Coke La Rock shouted out rhymes over Herc's instrumental beats.

While there is evidence that foundational elements of hip-hop emerged long before it boomed out of that South Bronx party — listen to Pigmeat Markham's "Here Comes The Judge" from 1968, for example — this momentous day, Aug. 11, 1973, would become known as the origin of hip-hop, with Herc being anointed the genre's founding father.

What began as a local sound and burgeoning scene in the "Boogie Down Bronx" has since evolved into a global movement. Hip-hop today is a powerful, unapologetic force that has influenced every genre of music and impacted every facet of society and pop culture around the world. Over the past five decades, the sound has expanded as a multi-genre invention. The party-starting, feel-good rhymes of the Sugarhill Gang's "Rapper's Delight," the first global rap hit, paved the way for the piercing social commentary and "reality rap" fueling Grandmaster Flash & the Furious Five's hit single "The Message," the latter of which can be traced to current-day rap prophets like Kendrick Lamar and Noname. 

As the world celebrates the 50th anniversary of hip-hop this year, GRAMMY.com is honoring some of the genre's most impactful artists, producers and creators in our inaugural 50 Artists Who Changed Rap list. Through this wide-spanning list, we are paying tribute to the pioneers, originators and futurists who have shaped hip-hop culture, pushed the artistic boundaries of rap over the past five decades, and continued to evolve the sound into the future.

To be clear, this list is not a ranking of the "best" rappers, nor is it a voting-based compilation of the top-selling artists in hip-hop. Rather, it is meant to serve as a survey of some of the most influential and impactful artists who have shaped rap music and hip-hop culture over the past 50 years.

To help compile our list of these 50 influential artists, GRAMMY.com invited an industry panel of established music veterans, cultural and music journalists, published authors, and music historians, who collectively submitted hundreds of artists suggestions. (See the full list of contributors below.) Based on these initial submissions from our industry panel, the artists comprising the final list, presented below in no ranking order, were selected based on a wide yet loose range of indicators: creative and artistic impact; career evolution and longevity; classic and influential albums; and beyond.

Of course, no one list could ever contain the whole of hip-hop and its ever-expansive reach. Nor could any list of influential rappers be whittled down to a mere list of 50. That's an impossible feat. Rather, our 50 Artists Who Changed Rap list stands as a love letter to some of the culture's defining moments and impactful voices that have helped create a global movement that continues to inspire and ignite future generations from all walks of life.

"As we approach hip-hop's 50th anniversary, it's important to acknowledge all of its accomplishments and the people in it," Len Brown, Senior Project Manager of Awards and Rap, Reggae, and R&B Genre Manager for the Recording Academy, shares. "What was once thought of as a passing fad has become the world's biggest genre despite it being the youngest — all made possible by the ingenious minds that continuously push the boundaries of music. There are countless individuals who got us this far and countless more who'll continue to carry the culture for the next 50 years and beyond."

There is so more to be said about our beloved hip-hop culture. Its history is rich and deep, while its future is still being written by today's leading lights and new, emerging voices revolutionizing rap. Today, we offer you this list as your jump-off to celebrate hip-hop in all its glory as we honor 50 Years of Hip-Hop all year long.

Explore the music from every artist featured in our 50 Artists Who Changed Rap list in an exclusive playlist, curated by longtime GRAMMY.com contributor and hip-hop tastemaker Kevin L. Clark, on Amazon Music, Spotify, Apple Music, and Pandora.

Visit our Rap genre page for more exclusive content and to explore some of the rap's most memorable moments in GRAMMY history across the decades. Continue to visit GRAMMY.com for more exclusive 50 Years of Hip-Hop content throughout the year.

 — Kevin L. Clark & John Ochoa

2 Live Crew

All titillating, risqué elements of hip-hop's artistry — hits from Nicki Minaj's "Anaconda" to Cardi B's and Megan Thee Stallion's "WAP" to Sexyy Red's "Pound Town" — owe a sizeable debt to Miami rap quartet 2 Live Crew. As regions in the American West and South first made their presence known in hip-hop during the late 1980s, 2 Live Crew — "Uncle Luke" Campbell, the late Fresh Kid Ice, Brother Marquis, DJ Mr. Mixx — introduced the bottom-heavy Miami bass sound to the culture with their ribald 1986 single, "Throw the D." Pioneering a frat-party climate incorporating stripper-influenced female stage performers and comical, sexually explicit material on The 2 Live Crew Is What We Are (1986) and Move Somethin' (1988), the group  soon ran afoul of authorities who deemed their albums legally obscene, becoming the first act to release the first sound recording to be declared obscene.

The first act in music history to release profanity-free, "clean" versions of their albums, 2 Live Crew soldiered through legal battles fighting for their freedom of speech that eventually ruled in the group's favor. In obscenity trials across the early '90s tied to the Crew's hit 1989 album, As Nasty as They Wanna Be, which was ruled obscene and illegal to sell in 1990, the group was ultimately acquitted of the charges, with the U.S. 11th Circuit Court of Appeals holding that the music held artistic value, despite its graphic contents. Through these legal cases, 2 Live Crew arose as the unlikeliest champions of freedom of speech, with First Amendment advocates and major artists, including David Bowie, alike defending the group's artistic freedom and protected speech.

A separate legal skirmish, in which the group was sued for copyright infringement over a parody they recorded of Roy Orbison's "Oh, Pretty Woman," made its way to the Supreme Court. The Court held the music as parody and therefore cleared as fair use rather than copyright infringement; this case against 2 Live Crew ultimately established that a commercial parody is covered under fair use laws.

Today, 2 Live Crew albums allow hip-hop a sexual freedom of expression that infuses the work of current acts from Plies to City Girls. — Miles Marshall Lewis

2Pac

2Pac, born Tupac Amaru Shakur, was born into activism; his mother, Afeni Shakur, and biological father, William Garland, were both Black Panthers. He once famously said, "I'm not saying I'm gonna change the world, but I guarantee that I will spark the brain that will change the world," a hip-hop quotable that suggests his influence is still igniting brains for metamorphosis.

Shakur's rap career was incubated by Oakland's Digital Underground, who took him on tour as a roadie and dancer and collaborated with him. DU's politically aware yet party-loving ethos helped inject some fun into Shakur's edge. He'd later define this as "THUG LIFE," standing for "the hate u give little infants f— everyone," an eternal hip-hop mantra, also emblazoned as an iconic tattoo across this torso,  that would become highly mimicked by rappers who wished to follow in his footsteps.

Known for working furiously in the studio, Shakur sensed he would die young and he wanted to leave a lot behind. He released four albums between 1991 and 1996: 2Pacalypse Now, Strictly 4 My N.I.G.G.A.Z…, Me Against the World, and All Eyez on Me. He also left behind enough material for seven posthumous albums — six solo works and one collaborative album with Tha Outlawz. Throughout his discography, he spoke truth to power, rapping about the harsh realities of hood life ("Changes"), female empowerment ("Keep Ya Head Up"), and eternal maternal love ("Dear Mama"). He also knew how to throw down a party anthem as heard on "California Love" and "I Get Around."

The life and legacy of Shakur, who was killed in 1996, continues to be studied and valued in the present. From his never-before-heard appearance in Kendrick Lamar's instant classic, To Pimp A Butterfly, to Dear Mama, an acclaimed docuseries about his relationship with his mom, which premiered in April on FX, Pac's influence will never wane; his recent Hollywood Walk of Fame star unveiling is a testament to that fact. — Tamara Palmer

Watch: 2Pac's All Eyez On Me Turns 25: For The Record

50 Cent

Queens, New York, native Curtis "50 Cent" Jackson's impact on hip-hop is undeniable — and far-reaching. In a span of roughly 20 years, the rapper has released five successful studio albums, produced a slew of successful television shows, created a record label, G-Unit Records, founded his own cognac brand, and had a hand in other fruitful business ventures. His placement on this list is palpable.

Before his major-label debut, 50's mixtapes, including Guess Who's Back?, flooded the streets and generated a large fanbase that helped aid his breakthrough success. After being discovered by Eminem and signed to Shady/Aftermath Records, 50 worked with legendary producer Dr. Dre to create his blockbuster debut album, Get Rich or Die Tryin' in 2003. A commercial success, going 9x platinum, the seminal album showed audiences 50's lyrical prowess as well as his mainstream crossover reach. 50 Cent's career evolution, talent and success have left an indelible mark that will be seen and felt for generations to come. — Rachel McCain

Explore More: 19 Concerts And Events Celebrating The 50th Anniversary Of Hip-Hop

A Tribe Called Quest

Composed of Q-Tip, the late Phife Dawg, occasional member Jarobi White, and DJ Ali Shaheed Muhammad, A Tribe Called Quest helped carve a space for rappers (and rap listeners) with a bohemian bent to their hip-hop aesthetic. Formed by high school friends from Queens, New York, the group established its own unique sound through the use of jazz and rock samples, a practice then unorthodox for hip-hop in the early 1990s. Early on, they helped create a bridge between jazz and hip-hop, two worlds then often seen as distantly disconnected. Legendary jazz bassist Ron Carter, for example, guested on A Tribe Called Quest's seminal sophomore album, The Low End Theory, marking one of the earliest collaborations between jazz and hip-hop musicians.

Widely considered to be masterpieces of the genre, People's Instinctive Travels and the Paths of Rhythm (1990), The Low End Theory (1991), and Midnight Marauders (1993) — their initial trio of albums — established A Tribe Called Quest as mavericks of sound and sonic visionaries.The group's final studio album, We Got It from Here…Thank You 4 Your Service (2016), featured appearances by Elton John and Jack White — exemplifying the group's reputation as genre-inclusive pioneers of alternative hip-hop.

A Tribe Called Quest's Afrocentric, left-of-center, cultural nationalist aesthetic set them apart as iconoclasts, clear antecedents to the likes of OutKast, Kanye West, Tyler, the Creator, and so many others. — Miles Marshall Lewis

Explore More: For The Record: A Tribe Called Quest's Groundbreaking The Low End Theory At 30

Big Daddy Kane

Antonio Hardy, aka Big Daddy Kane, is your favorite rapper's favorite rapper — a skilled, all-around technician with an unrelentingly charismatic appeal. His impeccable '80s styling – replete with velour suits, gold accessories, and a high-top fade — accentuated his innovative rhyme schemes, honed from his time as a battle rapper from Brooklyn prior to linking with Marley Marl's Juice Crew alongside friend and collaborator Biz Markie. His debut single, "Raw," was an underground sensation, introducing a new style of rhyming: quick and in syncopation with complex drum schemes without sacrificing articulation. Long Live the Kane, Kane's first album, is a showcase of his prodigious talents on the microphone: Where "Set It Off" unleashed his array of dizzying rhymes with locomotive speed, "Ain't No Half-Stepping" was a casual stroll through extended metaphors, maximizing the suave and commanding texture of his voice as it lingered on the beat. 

Kane was simultaneously a powerful MC and a sex symbol; he would lean into his "loverman" appeal with hits such as his chart-topping "Smooth Operator," a relaxed and polished display of lyrical finesse over a blend of samples including "All Night Long" by the Mary Jane Girls, Isaac Hayes' "Do Your Thing and Marvin Gaye's "Sexual Healing." Kane succeeded at being the player, lyrical assassin, an Afrocentric rhyme-spitter all in one — a level of dexterity that would influence a number of greats that followed him, from Jay-Z to Eminem to Black Thought to Notorious B.I.G. — Shamira Ibrahim

Chief Keef

Chief Keef started his career as rap's Ozzy Osbourne, the most visible figure in a burgeoning scene as exciting as it was controversial. But over the last decade, he has morphed into hip-hop's Brian Eno, making ever weirder projects while retaining something close to A-list name recognition. When Keef emerged in the early 2010s thanks to thundering singles "I Don't Like" and "Love Sosa" and support from stars like Kanye West and 50 Cent, the music industry seemed hellbent on sanding down his edges. The resulting album, 2012's Finally Rich, went platinum, but it gave fans little indication of the auteurist approach that would come to define the rest of Chief Keef's career. 

Since eschewing mainstream success, Keef has honed his eccentricities on a series of excellent mixtapes, including Thot Breaker (2017), a delightfully strange project filled with slurred melodies and chirping synths. As one of the chief pioneers of drill, his most palatable impact on rap is perhaps heard across the international drill scenes bubbling up across underground scenes around the world. Without Keef, drill would not be the dominating subgenre in rap it is today. Still just 27, Keef has settled into a role not just as your favorite rapper's favorite rapper, but as one of their go-to producers: He's crafted wonderfully bizarre soundscapes for Lil Uzi Vert, Coi Leray, and YoungBoy Never Broke Again. — Grant Rindner

Explore More: Essential Hip-Hop Releases From The 2010s: Ye, Cardi B, Kendrick Lamar & More

De La Soul

Completely innovative for their era, De La Soul heralded the entrance of nerdy wunderkinds into a hip-hop culture then full of machismo and blustering bravado. High school friends from suburban Long Island, New York, Kelvin "Posdnuos" Mercer, the late Dave "Trugoy the Dove" Jolicoeur, and Vincent Mason, aka DJ Maseo, debuted as teenagers with 1988's verbally obstruse "Plug Tunin'." A masterful full-length debut, 3 Feet High and Rising (1989), contained a wide-ranging sonic collage of stacked samples and highly diversified snippets of sounds, placing Sly Stone alongside Steely Dan and beyond. 

The groundbreaking production style led to a lawsuit by the Turtles, the 1960s rock band who demanded royalties for the use of 12 seconds of their music on the album. A legal decision in the Turtles' favor changed sampling laws forever, but De La Soul kept the innovation coming throughout a catalog of classics, including De La Soul Is Dead, Buhloone Mindstate and Stakes Is High, which is now, thankfully, available on all DSPs to inspire future generations to come. — Miles Marshall Lewis

DJ Jazzy Jeff & The Fresh Prince

"We wanna let everybody know where it's at. It's right here — ‘Yo! MTV Raps.’" The skinny guy in the orange tank top and MTV baseball cap rapping into the camera was still years away from having his own sitcom, and further still from being one of the most bankable movie actors on the planet. But if you happened to be watching the premiere episode of “Yo! MTV Raps” on Aug. 6, 1988, you would see one thing clearly: Will Smith exploded off the screen. The guy was a star.

Will teamed up with the virtuosic DJ Jazzy Jeff, and the group's beatboxer Ready Rock C, back in 1985. By the time of the “Yo!” appearance, they already had two albums under their belt, including He's the DJ, I'm the Rapper (1988). That record, hip-hop's first-ever double album, ensured the group's place in history. Jeff's innovative DJ skills were front and center on songs like "Jazzy's In The House" and "DJ On Wheels," while Will brought his storytelling charm to "Parents Just Don't Understand" and "A Nightmare on My Street." Will's lyrics were funny and universal — you didn't have to be from the Bronx, or even West Philly, to relate to being scared of Freddy Kreuger. Plus, as Ann Carli, then a Jive Records exec, recalls during the "Parents…" video shoot, as quoted in Brian Coleman's indispensable tome, Check the Technique, Vol. 2, "The camera loves him."

From there, it was off to the races. More hit songs, TV and movie stardom, jumping out of planes, and all the rest. But it all started with a rap group that combined two world-class talents into a GRAMMY-winning package that all the world could love. — Shawn Setaro

Watch: GRAMMY Rewind: DJ Jazzy Jeff & The Fresh Prince Win For 1991 Bop "Summertime"

DJ Kool Herc

Clive "DJ Kool Herc" Campbell is an essential part of hip-hop's origin story. His younger sister, Cindy Campbell, asked him to play at a "Back to School Jam" she organized for Aug. 11, 1973, much like the ones she organized within the 1520 Sedgwick Avenue recreation room. At the party, today considered the day when hip-hop was born, Campbell introduced his "merry-go-round" turntable method in which he isolated the instrumental breakdowns in funk records for the "beat boys" in attendance. Over the next few years, as the legend of the party grew, Campbell established himself as a top DJ in the area, thanks in no small part to a massive sound system he built and the presence of helpers — dancers, fledging MCs and DJs, security — called the Herculoids, named after the Hanna-Barbera cartoon. In 1977, Herc was the victim of a stabbing at a local nightclub, an incident Bronx pioneers believe marked the end of his dominance and allowed rivals to surpass him. However, DJ Kool Herc remains a Promethean figure who sparked the beginning of what would later be known as hip-hop. He's the ultimate reason we're all celebrating 50 Years of Hip-Hop this year. In November, he will be inducted into the Rock and Roll Hall of Fame. — Mosi Reeves

Explore More: Founding Father DJ Kool Herc & First Lady Cindy Campbell Celebrate Hip-Hop’s 50th Anniversary

DJ Screw

Less than 20 years after the 1977 New York City blackout, where Black youth across the boroughs of New York City came upon DJ equipment and found ways to use technology to achieve their dreams, a man named Robert Earl Davis Jr., also known as DJ Screw, used two turntables to fulfill his artistic dreams, while simultaneously establishing Houston a rap capital. When DJ Screw emerged in the 1990s, the predominant rap sound and DJ technique were East- and West Coast-focused. But when DJ Screw introduced his "chopped and screwed" style, his signature DJ technique that slowed records to create pockets for the beats to flow, windows of opportunity opened for rappers across Houston to join the fold. 

He created a kaleidoscope, a purple-tinted portal where Southern rappers traveled through region and time to tell their stories. There was not a street or avenue in Houston or the South where chopped and screwed could not be heard from a nearby car or window. He gave Houston and the South an opportunity to be heard within the boisterous noise of bicoastal hip-hop. In the 23 years since his passing, his chopped and screwed sound has been used by the world's greatest entertainers — horror auteur Jordan Peele has used chopped and screwed sounds in scenes and trailers for hit films like Nope and Us — and created an entry point for Houston to achieve worldwide cultural and musical success. All because of one man and his turntables. — Taylor Crumpton

Explore More: Learn From Texas: How A New Generation Of Artists And Creatives Is Blazing Trails In Today's Texas Rap Scene

Doug E. Fresh & Slick Rick

Throughout the early 80s, Douglas "Doug E. Fresh" Davis built a reputation for vocal percussion, or "beatboxing," and recorded a few 12-inch singles while collaborating with the likes of Kurtis Blow and others. In 1984, he recruited a teenage MC, Ricky "Slick Rick" Walters, to join Doug E. Fresh & the Get Fresh Crew. In 1985, the group released "The Show / La-Di-Da-Di," a gold-certified 12-inch that highlighted both Fresh's talents as a Master of Ceremonies and Rick's unforgettably British-inflected voice and sly, witty lyrics. 

Listen: Essential Hip-Hop Releases From The 1980s: Slick Rick, RUN-D.M.C., De La Soul & More

After going their separate ways, the two continued to have a major impact during the early years of rap's golden age. One of hip-hop's great entertainers, Doug E. Fresh scored several hits over the next few years like the spiritually inspired "All the Way to Heaven" (1986), the anti-drug protest "Nuthin'," and "I-Ight (Alright)" (1993). Slick Rick's storytelling prowess and use of off-key vocal harmonies, as showcased on his platinum solo album The Great Adventures of Slick Rick, made him a major influence on subsequent generations of rappers. This year, he received a Recording Academy Lifetime Achievement Award. — Mosi Reeves

Explore More: Slick Rick Receives the Lifetime Achievement Award at the 2023 GRAMMYs

Dr. Dre

Born Andre Young in Compton, California, Dr. Dre is one of hip-hop's definitive and standard-setting pioneers. Now a veteran DJ, artist and producer, Dr. Dre's public story began as a member of two very different, influential L.A. groups in the '80s: electro stars World Class Wreckin' Cru and gangster rap icons N.W.A; the latter is the subject of a popular 2015 biopic, Straight Outta Compton, and earned Dre international recognition for bringing the reality and struggles of inner-city street life to mainstream America.

Dr. Dre took home the first of his seven GRAMMY wins to date in 1994. That year, he won the GRAMMY for Best Rap Solo Performance for "Let Me Ride" from The Chronic, his groundbreaking, triple-platinum album, which has launched official international Dre Day celebrations every year since its release and helped normalize weed culture around the world. More golden gramophones have followed for his work with Eminem and Anderson .Paak, and he's also been nominated for his productions for Kendrick Lamar, 2Pac, 50 Cent, Gwen Stefani, and more.

Dr. Dre's ear for music has helped him become a billion-dollar entrepreneur as well. In 2006, he and his close business associate, Interscope label head Jimmy Iovine, created Beats Electronics to sell Beats By Dre headphones, which quickly set style and sales trends in the audio technology sector. Eight years later, Apple acquired Beats for a reported $3 billion. But with his GOAT-status secured, Dre didn't stop there. Over the years, he's helped carve the future for the next generation of music minds. He opened a magnet school in South Central's historic Leimert Park and co-founded the Jimmy Iovine and Andre Young Academy at the University of Southern California. At the 2023 GRAMMYs, Dre received the inaugural Dr. Dre Global Impact Award for his innovations and achievements throughout decades-long career. — Tamara Palmer

Explore More: Dr. Dre's The Chronic: 25 Years Later

Drake

Who would've thought an actor from the Great White North would end up becoming one of the world's biggest pop culture icons? Drake's role on the popular Canadian teen drama series "Degrassi: The Next Generation" was simply a launching pad for a music career that would not only cross Canadian-American borders, but showcase the true universality of hip-hop. His signature R&B crooning melting over melodic rap beats, which began with his breakthrough mixtape So Far Gone (2009), halted the gangster mentality that ruled hip-hop in the late '00s.

Listen: 5 Essential Hip-Hop Releases From The 2020s: Drake, Lil Baby, Ice Spice, 21 Savage & More

From there, Drake surged as rap's global leader with classics like Take Care (2011) and If You're Reading This It's Too Late (2015). And while not his most acclaimed album, the commercial and international success of his 2016 blockbuster, Views, paired with a thrilling foray into dancehall and Afrobeats proved that he could take hip-hop into different pockets around the globe. He perfected his formula — a mix of tearful emotions, flirtatious loverboy charm, a braggadocio attitude, viral one-liners, and the ability to mold to various cultural sounds — and spun it into gold and platinum success. From currently holding the record for the most Top 10 hits on the Billboard Hot 100 to building his OVO Music empire, Drake still holds the mainstream industry in the palm of his hand to this day. — Bianca Gracie

Read More: How Drake & 21 Savage Became Rap's In-Demand Duo: A Timeline Of Their Friendship, Collabs, Lawsuits And More

E-40

With his colorful "slanguage" and consummate cool, E-40 has influenced MCs all over the world. The rapper, born Earl Stevens, built his label Sick Wid It through independent record sales, a hustle he learned from his uncle, the soul singer Saint Charles Thurman, who started the first distribution company for Black music in the Bay Area. 

That independent strategy inspired like-minded artists to follow E-40's path: make millions on the streets and in the boardrooms. Most prominently, labels such as Cash Money Records and No Limit Records in New Orleans gave him foundational props; Master P started his No Limit Records inside a record store in Richmond, California, before returning to the South. After signing with Jive Records, E-40 released an impressive discography that includes three gold albums and one platinum album.

Continuing to expand his artistry in more recent years, E-40 has released songs and toured as one-quarter of the rap supergroup Mount Westmore alongside Too $hort, Ice Cube and Snoop Dogg. He has parlayed that independent hustle into building his own companies to sell alcoholic spirits and food, now stocked in liquor stores, grocery markets and big box stores like Costco. His debut cookbook, Goons With Spoons, created in conjunction with Snoop Dogg, will be released in November.

A community-minded philanthropist, E-40 has long given back to his communities. In 2023, he donated $100,000 to Grambling University, which he attended, to create the Earl "E-40" Stevens Sound Recording Studio on campus. And his do-it-yourself ethos continues to be seen today in the likes of fellow Bay Area rappers, including LaRussell and Larry June, and the next generation of MCs. — Tamara Palmer

Eminem

The career of Eminem, born Marshall Bruce Mathers III, is unprecedented. The two biggest rap albums in American history are both his. Out of the 20 rap albums with the largest first-week sales, he has six. He is the best-selling rapper of all time and the best-selling artist of any type in the 2000s.

But sales are only the beginning of the story. For a few years in the late 1990s and early 2000s, Eminem was the center of pop culture. His songs and antics created heated debates, which created even more songs and even more antics, in a feedback loop that grew giant enough to eventually include a still-powerful duet from Elton John and Em the GRAMMYs. Eminem brought the singer with him to perform at the 2001 GRAMMYs ceremony as an implicit answer to charges of homophobia that had been dogging him since he first exploded into the mainstream with controversial lyrics.

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Eminem was always more than controversy, though. While his sales, as he was the first to admit, were boosted by his race, his skill level was never at issue. His blazingly technical raps were in service of a captivating life story. Before he was rhyming about reporters and politicians reacting to his contentious raps, he was spitting about being at "rock bottom" — depressed, hopeless, and struggling to get by. If there were something that fans of all backgrounds could relate to, it was not giving a f—. — Shawn Setaro

Read More: Sent Here To Destroy Us: Eminem’s The Marshall Mathers LP At 20

Eric B. & Rakim

One of the greatest hip-hops duos ever, Long Island duo Eric B. & Rakim symbolized hip-hop music at its most refined. Thanks to his late-'80s recordings with DJ/producer "Eric B." Barrier, William "Rakim" Griffin is often mentioned as the greatest MC of all time. His relaxed vocal presence, subtle use of Five Percenter Nation teachings, storytelling prowess, and ability to weave complex ideas into accessible lyrics have been mimicked by countless others. Considered an essential artifact of hip-hop's late-80s golden age, Paid in Full, the duo's 1987 debut album, is packed with hits like "Eric B. Is President," "My Melody," "I Know You Got Soul" — which popularized the use of James Brown samples in rap records — and "Move the Crowd."

Their second album, Follow the Leader (1988), marked a new peak in Rakim's lyrical abilities, while Let the Rhythm Hit 'Em (1990) was one of the most anticipated albums of the era. Before the group split and Rakim embarked on a solo career, they released Don't Sweat the Technique, which has recently achieved new popularity due to its use on television and in film. — Mosi Reeves

Future

Atlanta had a major resurgence in the 2010s — and Future led the charge. A Dungeon Family member, he used Auto-Tune to create a dreary version of trap blues as he warbles about addiction, depression, manipulative relationships, and heartache. He solidified his legacy in 2015 when he unleashed a string of projects: the Beast Mode and 56 Nights mixtapes, the chopped-not-slopped DS2 album, and the What a Time to Be Alive collaborative mixtape with Drake, which highlighted Future's brilliant chemistry with rap's current titans. The onslaught of music spun a dark cloud over the rap genre, giving the green light for male rappers to be just as emotional as they are vengeful. Future's hot streak continues to this day: He's experimenting with new genres, including pop star collaborations with Ariana Grande and Taylor Swift; churning out hits, most recently the GRAMMY-winning "Wait For U" with partner-in-music Drake; and still confidently wearing his broken heart on his sleeve. — Bianca Gracie

Grandmaster Flash & the Furious Five

As one of many who followed in DJ Kool Herc's wake, Joseph "Grandmaster Flash" Saddler is a key innovator in the art of DJing, particularly in the way he mixed records and expanded on scratching, a technique first invented by Grand Wizzard Theodore. In the late 1970s, he assembled the crew of MCs who became the Furious Five and who would go on to release several classic hip-hop records: Keith "Cowboy" Wiggins, who is credited with the first use of the phrase "hip-hop," Melvin "Melle Mel" Glover, Mel's brother Kidd Creole, Guy "Raheim" Williams, and Eddie "Scorpio" Morris.

In 1979, the group recorded "Superrappin'," which many consider the first "real" Bronx hip-hop record. They then released several popular 12-inches that culminated in "The Message" (1982), a watershed moment in rap's development into a full-fledged musical artform. Meanwhile, Grandmaster Flash created "The Adventures of Grandmaster Flash on the Wheels of Steel," a showcase for his historic DJ skills that's considered the first turntablism record. In 2007, Grandmaster Flash & the Furious Five became the first hip-hop group inducted into the Rock and Roll Hall of Fame. In 2021, the group received a Recording Academy Lifetime Achievement Award. — Mosi Reeves

Learn More: Essential Hip-Hop Releases From The 1970s: Kurtis Blow, Grandmaster Flash, Sugarhill Gang & More

Ice-T

Though Tracy "Ice-T" Morrow wasn't the first L.A. rapper to make a song about street life — he prefers the term "reality rap" instead of the mainstreamed moniker "gangsta rap" — he was arguably the most important. After a few years in the electro scene, marked by a performance in the 1984 film Breakin', Ice-T's "6 in the Mornin'," a vivid tale about a young hustler slanging dope and avoiding cops, made a huge local impact; it continues to influence rap artists to this day. In 1987, he became the first West Coast rapper to release an album on a major label with the gold-certified Rhyme Pays. By the time of his second album, Power (1988), Ice-T was widely considered the top solo rapper on the West Coast, while The Iceberg (Freedom of Speech..Just Watch What You Say) (1989) saw him expanding into social commentary and hard-rock experiments. His fourth album, O.G. Original Gangster (1992) introduced Body Count, a pioneering heavy metal/rap band that predicted the rise of rap rock. — Mosi Reeves

Watch: Hip-Hop History On Full Display During A Star-Studded Tribute To The 50th Anniversary Of Hip-Hop Featuring Performances By Missy Elliott, LL COOL J, Ice-T, Method Man, Big Boi, Busta Rhymes & More | 2023 GRAMMYs

J Dilla

Inimitable in sound and rhyme, Detroit's own James Yancey, also known as J Dilla, is respected around the world as "your favorite producer's favorite producer." A beloved and highly esteemed songwriter, producer, rapper, and drummer, he is a great influence on some of hip-hop's most diverse voices across the decades and to this day. 

As a member of Slum Village, Dilla would quietly lace beats from his mother's basement for the likes of A Tribe Called Quest ("Find A Way"), Erykah Badu ("Didn't Cha Know"), MF DOOM ("Gazzillion Ear"), and countless others. Umpteen tributes on tracks and in concerts and from groups such as NxWorries (consisting of Anderson .Paak and Knxwledge), television programs (Cartoon Network's Adult Swim), and institutions (Smithsonian's National Museum of African American History and Culture) harken to his significant contribution to this thing we love called hip-hop. 

Considered one of the greatest creatives in hip-hop history, J Dilla made innovative use of sound and imagination by employing real-time rhythms that may better translate as "a vibe" for listeners. He is directly responsible for bridging the soul and the sonic that distinguish rap as one of the most inventive art forms in recent history. Proving that his energetic beats matched his rhymes, Dilla's legacy continues to inspire and resonate within the hip-hop community today, and on hip-hop's milestone anniversary, his innovations and impact prove to be immortal, too. — Kevin L. Clark

Jay-Z

Born Shawn Corey Carter in Brooklyn, New York, Jay-Z has made an indelible mark on hip-hop culture over three decades by marrying superlative lyrical creativity with an acute business acumen. Storming the gates of the record industry as co-owner and marquee artist of the independent Roc-a-Fella Records label, Jay-Z released the seminal Reasonable Doubt — a debut that instantly placed him among the top rappers of the 1990s. A consistent release schedule of unforgettable material, including Vol. 2…Hard Knock Life, The Blueprint, The Black Album, and 4:44, created summertime classics for a whole generation while establishing him as one of the greatest rappers the culture has ever produced. 

Jay-Z occupies a unique space in hip-hop as both a billionaire mogul and a rapper consistently recognized as one of the art form's all-time most talented. His stakes in various entrepreneurial ventures — the music streaming platform Tidal; the entertainment agency Roc Nation; the 40/40 Club sports lounge — lend as much to his legacy as his one-time rivalry with Nas, which resulted in hip-hop's most notorious battle between livi de ng MCs to date. His marriage to Beyoncé Knowles-Carter, one of the most iconic pop performers of the modern era, has also produced artistic contributions — see their joint album, Everything Is Love — as well as an enduring symbol of Black excellence. — Miles Marshall Lewis

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Jermaine Dupri

The son of storied music executive Micheal Mauldin, Jermaine Dupri has contributed to hip-hop as a producer, songwriter, and executive. Most importantly, the GRAMMY winner, who started dancing for the likes of Diana Ross and Whodini, helped cultivate Atlanta into the rap capital it is today.

As the founder of So So Def Records, Dupri helped make Kris Kross and Lil Bow Wow hit-making teen heartthrobs in a music genre that leaned on more adult personas; he also played a major role in helping Da Brat become the first female rapper to go platinum. Even today, his time as an executive producer of the reality competition series The Rap Game gave way to the eventual rise of next-gen rapper Latto. That doesn't even count collaborations that have reached nearly every corner of hip-hop, including classics with Jay-Z, UGK, Bone Thugs-N-Harmony, Snoop Dogg, and more. 

Dupri's legacy in hip-hop can also be heard in the musical bridge connecting rap and R&B. He's written and produced hit albums for Mariah Carey, Usher, Xscape, Jagged Edge, and countless more, his contributions furthering the bond between the two genres. — Ural Garrett

Kanye West

Where do we even begin? From producing some of the greatest rap songs of the 2000s as Jay-Z's protégé to emerging as one of the most critically and commercially successful rappers of all time, Kanye West might be the most important musician of the 21st century — genre irrelevant. His ability to toggle between incisive commentary ("All Falls Down," "Heard 'Em Say"), all-time braggadocio ("Can't Tell Me Nothing," "Power"), and wry humor ("Gorgeous," "Otis") made his every verse an event, and his blockbuster albums consistently showcased an expert sense of talent curation. In the early 2010s, when West made a hard pivot from the maximalism of his magnum opus, My Beautiful Dark Twisted Fantasy (2010), to the industrial brutality of Yeezus (2013), he showed the kind of fearlessness that truly great artists possess, as he continued to push boundaries even in the face of skepticism.

The last several years of the Kanye West experience have been difficult and disturbing for many music fans. He's praised Adolf Hitler and made antisemitic comments, only to seemingly walk it all back, in a trollish fashion, albeit. A generational talent who has evolved his creative legacy in more ways than one, West's impact on music is clear and undeniable. Has he gone from industry iconoclast to outright outlier? Who's story is it to tell? But any attempt to wrap your mind around the first half-century of hip-hop history, and music in general, must include a reference to Kanye, whose DNA will be present in rap music for the next 50 years, at least.  — Grant Rindner 

Watch: GRAMMY Rewind: Watch Kanye West Honor His Late Mother As He Wins Best Rap Album In 2008

Kendrick Lamar

In retrospect, Kendrick Lamar's renowned verse on "Control" might be better described as a manifesto rather than a call to war. After name-dropping nearly a dozen of the hottest rappers of the time, including the likes of Drake and J. Cole, Lamar challenges, "What is competition? I'm tryna raise the bar high. Who tryna jump and get it?" Ten years and one legendary career later, Lamar's three minutes of rhymes come off as less of a widespread diss and more of a statement of intent.

The Compton native went on to reach heights hip-hop had never seen before. In 2018, the 17-time GRAMMY winner won the Pulitzer Prize for DAMN., an achievement once described as "a watershed moment … and a sign of the American cultural elite's recognition of hip-hop as a legitimate artistic medium."

Still, despite such momentous contributions to the genre and culture at large, pinning down Lamar's direct influence on hip-hop really makes you stop and think. Perhaps that difficulty stems from the fact that so much of what makes Lamar great is his ability to combine the top traits of those who came before him. Whether it be channeling the narrative superpower of Nas on good kid, m.A.A.d city, the powerful social commentary of 2Pac on To Pimp A Butterfly, or the vulnerability of Jay-Z on tracks like "Mother I Sober," Lamar's biggest impact on hip-hop may just be the fact that he indeed raised the bar high for rap while embodying those who laid its foundation. — Taj Mayfield

Explore More: How Kendrick Lamar's 2023 GRAMMYs Wins Bolstered His GRAMMYs Legacy

Kurtis Blow

A standard-setter who foreshadowed the international success of hip-hop, Kurtis "Blow" Walker is the genre's first superstar. Of his notable achievements, he became the first rapper to sign a major label deal (with Mercury Records) and the first to go gold via his 1980 single "The Breaks," which is recognized as one of the greatest hip-hop songs of all time and remains his signature calling card. 

Blow's enormous influence on the culture is directly tied to his ability to expand the boundaries of hip-hop and foster talent within and beyond his creative circles. His early DJ on the road was Joseph Simmons, who was nicknamed "Run, the Son of Kurtis Blow" and who later carved his own iconic career as one-third of the hip-hop trio Run-D.M.C. Blow and Run-D.M.C. starred in the 1985 movie Krush Groove, a fictional story that parallels that of New York label Def Jam Recordings, making Kurtis Blow essentially the first famous face in hip-hop to cross over into Hollywood.

In the mid-'90s, Blow became a radio DJ and hosted "The Old School Show" on Los Angeles radio station, Power 106. He was also ordained as a Christian minister, co-founded Hip-Hop Church, and released faith-based albums with his group, Kurtis Blow and the Trinity. Proving that hip-hop can coexist with gospel, Blow's spiritual-inspired music helped expand the audience for Christian music across genres and audiences. — Tamara Palmer

Ms. Lauryn Hill

With a pen in her hand, a song in her heart, and a story to tell, Ms. Lauryn Hill elevated hip-hop for the better during the '90s. Hill's work expertly blurs the lines between genres, often fusing doo-wop-flavored harmonies and '70s R&B with hip-hop swagger and the airiness of neo-soul. A Jersey native and member of the iconic rap group the Fugees, she became a household name after the international breakout success of her debut solo album, The Miseducation of Lauryn Hill (1998). The project sees the musician exploring themes of love, heartbreak and family through a personal lens with universal impact. A commercial and critical success around the world, the album won the GRAMMY for Album Of The Year in 1999, making Hill the first-ever rap artist to win that category. To this day, she counts eight GRAMMYs, the most of any woman in hip-hop.

Hill's melodic rap technique and artistic versatility have inspired acts across genre lines in the years since, from Drake to Lin-Manuel Miranda, who credits several elements in his Broadway hit "Hamilton" to her art. — J'na Jefferson

Learn More: Revisiting The Miseducation Of Lauryn Hill: Why The Multiple GRAMMY-Winning Record Is Still Everything 25 Years Later

Lil' Kim

Don't let her petite frame fool you: Lil' Kim has been larger than life since her 1994 debut as a member of Junior M.A.F.I.A. and mentee of the Notorious B.I.G. The Brooklyn native unlocked a next level for female rap with her 1996 debut solo album Hard Core. Even before the world heard the album, her seductive pose on the cover itself signaled a shift: It was time for women to take the lead. Hit singles like "No Time," "Crush on You" and "Not Tonight (Ladies Night Remix)" established the rapper's signature raunchy lyrics and guttural tone, flipping the male-dominated, often misogynistic genre on its head as she reclaimed her sexuality. She also knows how to command respect, spitting ferocious bars on songs like Diddy's "It's All About the Benjamins" and Mobb Deep's "Quiet Storm (Remix)" alongside her male counterparts.

A bonafide hip-hop icon, Lil' Kim's influence spans generations and industries. A muse for countless rising female rap stars and designers like Versace and Marc Jacobs alike, she carved a safe space for Black women in the often exclusive, white- and male-dominant fashion and music industires. Her sartorial choices, as eye-popping as her naughty rhymes, still give next-gen female rappers like Baby Tate, GloRilla, and Cardi B the Queen Bee-confidence to exude the same sense of sexual liberation she pioneered in rap in the '90s. Her path in both music and fashion have made her one of rap's most impactful voices with an undeniable legacy. — Bianca Gracie

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Lil Uzi Vert

Despite being a relatively new major player in the game, Lil Uzi Vert is an undeniable needle-mover in hip-hop. If that influence is hard to pin down, it's because Uzi has somehow made the existence of a quirky, emotional, rock-inspired rapper a common thing in 2023.

Similar to other breakout stars of the SoundCloud rap era who came up with them, including Lil Peep, XXXTentacion and Juice WRLD, Lil Uzi Vert brought their unadulterated self into their music. The result? A steady flow of evocative, genre-defying hits and deep cuts. From anthems like "XO TOUR Lif3" (2017) to "Rehab," a standout track off their recently released Pink Tape, the 27-year-old Philadelphia native consistently wears their heart and inspirations on their sleeve. Years worth of quality music coupled with their unwavering authenticity have forever broadened the horizons of hip-hop, making way for many future Lil Uzi Verts. — Taj Mayfield

Lil Wayne

There are two distinguishable eras in rap history: before Tha Carter and after Tha Carter. Lil Wayne, who's impact on the evolution of the genre is immeasurable, has taken rap to rare heights and forever changed its influence in and from the South. With an undeniable and almost insurmountable work ethic, New Orleans' native son has delivered infinite memorable moments that have spanned decades. From his show-stealing turns with Cash Money's the Hot Boys to his chart-decimating hits like "A Milli" to his genre-defining Tha Carter album series, Weezy F. has lived up to his reign as the "Best Rapper Alive" for decades.

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Boasting a deep appreciation for the culture, Wayne willed a layer of intuition and imagination that pushed rap to the next level. With a strength tougher than Nigerian hair, his impression can be heard throughout every era of modern hip-hop, from his own musical family tree with Young Money (Drake, Nicki Minaj) traced through to next-gen superstars (Kendrick Lamar, J. Cole).

Otherworldly, diverse, and an omnipresent influence in today's scene, Lil Wayne has been a blessing to rap, consistently pushing the game and growing the culture in immeasurable ways. — Kevin L. Clark

LL Cool J

There were rap albums before LL Cool J's Radio. But the genre was still largely singles-driven, and the albums then were usually stuffed with the hits, some filler, and a few unique experiments. It was Radio that turned the rap album into a work of art and kick-started the genre's golden age. 

LL was nothing if not versatile. He put out iconic singles like "I Need a Beat" and "Rock the Bells." His genre-shifting music videos, such as "Around the Way Girl," "Hey Lover," and the seminal classic, "I Need Love," added breadth to the male-dominated industry. And his show-stopping appearance in the film Krush Groove aided in turning the young MC into a king from Queens.

He also set yet another trend: the "don't-call-it-a-comeback" comeback. After releasing two killer albums, LL dropped Walking With A Panther in 1989. While it was a commercial success, Panther was shunned by hip-hop artists and fans at the time, due to its mainstream crossover appeal, and LL was deemed over by the hip-hop community, out of touch with a conscious, Afrocentric age of the time. Barely into his 20s, it seemed his time was up. And then, he had rap music's first major comeback — lyrical protestation notwithstanding. Mama Said Knock You Out was a return to form that set LL Cool J up for a lifelong career in music, TV, movies, and even that whimsical song about his shark-fin-like hat. — Shawn Setaro

Mac Dre

Thanks to songs like "Thizzelle Dance" and "Feelin' Myself," Vallejo rapper Andre "Mac Dre" Hicks was the pied piper of hyphy, an innovation marked by bouncy bass and skittering funk rhythms. It dominated the Bay Area throughout the 2000s and remains a key component of the region's distinctive hip-hop scene.

Mac Dre's career dated back to 1989 with the local hit "Too Hard for the F—in' Radio." But in a case that made national headlines, he was arrested and convicted for allegedly being involved in bank robberies — his supporters continue to claim his innocence — and became the first rapper to make music, Back N Da Hood, while imprisoned. (He recorded his vocals over the phone.) When he finally returned to rap in the late '90s, he began refining his idiosyncratic style using P-funk tones and a droll and witty vocal tone. As expressed through songs like "Get Stupid" and "Not My Job," it was a style that eventually shook up the world and led to the foundation and popularization of the hyphy movement.

Unfortunately, Mac Dre didn't get to witness the peak and great success of his music, which was ultimately used in television and film as well as at sporting events. His unsolved killing in 2004 happened just as he seemed poised for a national breakthrough. — Mosi Reeves

Master P

The history of hip-hop is dotted with great business minds, but it's rare that someone's boardroom acumen proved so strong that their run of multiplatinum albums and smash singles feels entirely secondary. Such is the case with Master P, the New Orleans native who founded No Limit Records and, along with Cash Money's sibling duo of Bryan "Birdman" and Ronald "Slim" Williams, changed the paradigm of the rap mogul forever. In 1995, P partnered No Limit with Priority Records in a deal that saw him cover the brunt of the creative costs in exchange for greater creative control and backend profits. 

He broke through as an MC with Ice Cream Man and Ghetto D, albums that served more as showcases for the No Limit collective than P himself. Ceding the showier roles and technical flair to collaborators like Silkk the Shocker, Mia X and Mystikal, Master P brought a kind of brute force charisma that's easy to see working for him wheeling and dealing behind the scenes. No Limit has evolved into an entity where pioneers like Mia X can celebrate women in hip-hop, while P continues to expand the empire through winning partnerships (Snoop Cereal) and new offerings (Rap Snacks) that created the reason this music industry owes gratitude to Master P.  — Grant Rindner

MC Sha-Rock

Though she may not always receive the fanfare of her more mainstream cohorts, MC Sha-Rock changed the hip-hop ecosystem forever when she hit the booth in the late '70s. Largely considered to be the first female rapper, Sha-Rock, known as the "Mother of the Mic," helped pave the way for every woman rapper on this list — and beyond. Though she has B-girl origins, the South-Bronx-bred spitter showcased her raw talent and confidence behind the mic. As a member of Funky 4+1, her natural charisma and ability established the blueprint for the future of women in rap. Though Funky 4+1 was the first hip-hop group to appear on national television, it wasn't until the '80s when women rappers began to break through on an international scale. You can thank Sha-Rock for first opening that door, shattering the glass ceiling, and ushering in a gender breakthrough that's helped women dominate rap today. — J'na Jefferson

Explore More: Ladies First: 10 Essential Albums By Female Rappers

MF DOOM

Whether fans tuned into MF DOOM or aliases such as Viktor Vaughn or King Gedorah, the rapper/producer born Dumile Daniel Thompson offered some of the most memorable art found in hip-hop.

A London native transplanted to Long Island, New York, Dumile began his career as Zev Love X, forming the group KMD with his brother DJ Subroc. But after Subroc's sudden death and their record label's refusal to release their album, Zev Love X went on hiatus — and returned as MF DOOM, donning a mask to combat the music industry's corruption. He built a prolific catalog inspired by comic books, cartoons, and the absurdities and mundanities of life, creating worlds that brimmed with vibrant wordplay. His husky voice, conversational flow, and impossibly intricate rhyme schemes comprised his calling card, along with equally absurd references and unpredictable punchlines.

DOOM earned a rep among indie rap's best in the early 2000s, but he became a rap deity with Madvillainy, the album that smartly paired him with producer Madlib's collection of obtuse jazz and TV samples that were just as mercurial. The record elevated DOOM's iconography and solidified him as one of rap's most distinctive creators ever, with fans and other MCs alike paying reverence. — William E. Ketchum

Missy Elliott

In the late '90s, thin was "in" and hypersexualized female rappers became commonplace. But a big woman with big talent — and an even bigger patent-leather blowup suit — snuck in to extinguish these industry standards, becoming the people's champ and an undisputed icon in the process. Missy Elliott's pleasingly off-kilter brand of bravado is marked by eye-catchingly creative music videos, like the aforementioned, star-making "The Rain (Supa Dupa Fly)," entertaining performance techniques, and next-level beats crafted by her and her longtime friend and fellow Virginian, Timbaland. She's created works of art that have stood the test of time, allowing her to see and receive her flowers while she can still smell them: During GRAMMY Week 2023, Missy received the Recording Academy Global Impact Award at the Recording Academy Honors Presented By The Black Music Collective event; later this year, she will become the first woman rapper inducted into the Rock and Roll Hall of Fame. By dismantling boundaries, Missy Elliott paved the way for hip-hop artists to be unapologetically themselves. — J'na Jefferson

Explore More: Revisiting Supa Dupa Fly At 25: Missy Elliott Is Still Inspired By Her Debut Record

N.W.A

Dubbed the "world's most dangerous group," gangsta rap pioneers N.W.A put Compton, California, on the map in the late '80s with their provocative music and a name that embodied their unflinching bravado: N—z With Attitudes.

At the time, acts like Public Enemy, Kool Moe Dee, LL Cool J, and Eric B. & Rakim dominated the airwaves, with songs about everything from love, partying and lyrical prowess to race and politics. However, few were as overly explicit and provocative as the rising stars from the West Coast who disrupted the industry with the release of their hard-hitting debut album, Straight Outta Compton, in 1988.

With a stacked lineup consisting of Eazy-E, Dr. Dre, DJ Yella, Ice Cube, and MC Ren, the L.A. natives rapped about gang violence, police brutality, street life, and hood experiences. They were accused of demeaning women and glorifying violence and drug use, and as their music continues to stoke controversy as hip-hop lyrics in court proceedings are subject to debate today, N.W.A's provocative debut resonates to this day through new generations of fans. While the group would go on to sell millions of records and produce three superstar solo acts, their timeless album and its definitive protest anthem, "F— tha Police," cemented their place in the pantheon of hip-hop, forever changing the culture and the world at large with its powerful message. The emotionally charged song offers a scathing critique of systemic inequality that reflects the frustrations that marginalized communities harness for the discrimination they continue to face decades after the track dropped. 

While their tenure was short-lived, N.W.A's paradigm-shifting music inspired a slew of acts that would leave their own stamp on the culture, including 2Pac, Snoop Dogg, Eminem, the Game, and DJ Quik. — Desiree Bowie

Explore More: N.W.A Are Straight Outta Compton: For The Record

Nas

A perennial member of every hip-hop lover's top five rappers of all time lists, Nas inherited the crown of rap's greatest golden-age wordsmiths upon releasing his 1994 debut album, Illmatic, which helped establish the legend's nearly 30-year stellar reputation for MCing. Son of jazz cornetist Olu Dara, Nasir bin Olu Dara Jones grew up in the Queensbridge housing projects in Queens, New York, also the home of fellow hip-hop luminaries like Roxanne Shanté and producer Marley Marl. During a period when the hip-hop aesthetic seemed forever redirected to the West Coast, Nas helped refocus attention back on New York City, the birthplace of the culture.

Following the killings of both 2Pac and the Notorious B.I.G., concerns rang out when a long-simmering rivalry between Nas and Jay-Z went public on diss tracks like "Ether" (2001) and "Takeover" (2001). Defying the worst of expectations, their war of words eventually morphed into both a professional relationship — Nas signed to Def Jam in 2006 with Jay-Z as the label's then-president — and creative bond, with the duo releasing a joint song, "Black Republican," in 2007). On a recent string of collaborations with producer Hit-Boy — including the GRAMMY-winning King's Disease (2020) — Nas has helped alter expectations around career longevity in hip-hop. — Miles Marshall Lewis

Explore More: Nas' Illmatic | For The Record

The Neptunes

The Neptunes — the production duo powered by the genius of Pharrell Williams and Chad Hugo — changed the sound of late-'90s and early-2000s hip-hop, jump-starting and transforming the careers of countless artists across every genre imaginable in the process.

After getting their start with New Jack Swing pioneer Teddy Riley, the Neptunes made a name for themselves by producing N.O.R.E.'s "Superthug" and Ol' Dirty Bastard's "Got Your Money" as well as albums for Clipse and Kelis. 

The start of their hip-hop takeover can, perhaps, be traced to 2000, when they produced Jay-Z's "I Just Wanna Love U (Give It 2 Me)." The song, which features Pharrell's memorable voice on the hook, became Hov's first No. 1 hit on the Billboard Hot R&B/Hip-Hop chart.

The hit also caught Britney Spears' attention, prompting her to enlist the Virginia Beach duo to write and produce "I'm A Slave 4 U," which marked a major turning point in her mature, new sound. The Neptunes also helped Justin Timberlake craft a new sound and image, producing much of his debut solo album, Justified.

The duo's off-kilter, funk-influenced sound made them sought-after — and heavily imitated — producers for much of the aughts. Some of their 2000s hits include "Hot in Herre" by Nelly, "Drop It Like It's Hot" by Snoop Dogg, "Money Maker" by Ludacris and "Milkshake" by Kelis. Pharrell also helped usher in the era when producers came to the forefront of the spotlight, rapping and singing in songs and appearing in music videos for the artists they produced.

Counting four GRAMMY wins, the pair won Producer of the Year in 2003 and Producer of the Decade in 2009 at the Billboard R&B/Hip-Hop Awards. In 2022, the Neptunes were inducted into the Songwriters Hall of Fame, a distinction that proves just how much they changed the sound of the culture and music as a whole. — Victoria Moorwood

Explore More: 4 Ways Pharrell Williams Has Made An Impact: Supporting The Music Industry, Amplifying Social Issues & More

Nicki Minaj

Nicki Minaj rewrote the rules of hip-hop through her unparalleled rhyming ability, an arsenal of flows, a collection of character-driven voices, and crossover success. As a result, she single-handedly elevated female rap in the mainstream in the 2010s. Her reign came during a time when hip-hop was still considered to be a male-dominated terrain. Nonetheless, she proved female rappers can keep up with the boys, though she regularly surpassed them in skill level. Her genre-bending hits showcase her versatility, and her writing and performance talents make her one of the hottest commodities in music. She not only took risks, she made hits: Counting 132 entries, Nicki Minaj holds the record for the most Billboard Hot 100 hits by a woman rapper. Thanks to Nicki Minaj — or Nicki Lewinsky, Nicki the Ninja, you know what it is — a new generation of female rap superstars gained the courage to make their own magic. — J'na Jefferson

Explore More: The Nicki Minaj Essentials: 15 Singles To Showcase Her Rap and Pop Versatility

The Notorious B.I.G.

Christopher "Biggie Smalls" Wallace, aka the Notorious B.I.G., is a titan in hip-hop history, a wordsmith whose lyrical potency is intensified by the brevity of his career. Wallace's gravitas — in physical stature and in reputation — belied his youth; as a Jamaican-American who grew up in Brooklyn's Clinton Hill neighborhood, bordering Bedford-Stuyvesant at the height of the crack era, he spent his early years navigating the threshold between civilian life and street life and brought those complexities to his songwriting and vivid storytelling. With the guidance of Sean Combs — who then went by the moniker Puff Daddy – Wallace quickly went from "Unsigned Hype" in The Source magazine to Bad Boy's marquee artist, crashing onto the charts in 1994 with his debut album, Ready to Die, at just 21 years old. 

The album is a balance of massive, radio-friendly singles with quasi-autographical, introspective records that are bracing in their emotional range and attention to detail: For every "Juicy," "Big Poppa," and "One More Chance," there's "Warning," "Gimme the Loot," and "Suicidal Thoughts." In each track, Biggie played with the morphology of words and rhyming cadences at will, stretching vowels and contracting them to a staccato-like delivery with the proficiency of a jazz musician. Wallace's cinematic approach to rapping became his signature. He would form the crew Junior M.A.F.I.A. in this image, crafting records such as "Get Money" and "Player's Anthem" — songs as entertaining as they were illustrative that also introduced the world to the force of nature that was Lil' Kim.

Explore More: A Big Band For Biggie: Celebrating The Notorious B.I.G. With A Classical Orchestra

His posthumous second album, presciently titled Life After Death (1997), is a sprawling double album replete with gangster epics such as "Somebody's Gotta Die," "N—s Bleed," and "What's Beef?" Released sixteen days after his killing in 1997, Biggie's mainstream crossover singles hit like a tidal wave. The chart-topping singles, "Mo' Money, Mo' Problems" and "Hypnotize," launched the patented Bad Boys formula of the renowned Hitmen production team into the stratosphere, eventually inspiring the likes of Kanye West and others to speed up soul samples to achieve similar success. Wallace's own vocals — heavy and lush, with the ability to glide like butter via a cascade of internal rhyme schemes — still sound as fresh today as they did when the project initially released to critical acclaim on March 25. And despite the tragic coda that cut short the life of this king from Kings County, the Notorious B.I.G.'s narrative prowess remains eternal.— Shamira Ibrahim

Explore More: Hip-Hop By The Borough: Unpacking The Sound Of Rap's Birthplace From The Bronx To Staten Island

OutKast

When OutKast's André 3000 proudly proclaimed "the South got something to say" at the 1995 Source Awards, the Atlanta rapper and his creative partner, Big Boi, had no idea of the significance those words would have on rap music today. At the time of their 1994 debut, Southernplayalisticadillacmuzik, the South was regarded as country, "backwards," and behind the times. Those words, a whistleblow, could've been misinterpreted by white and rural communities that these artists and their regions were not deemed "hip-hop." Hip-hop was cool, coastal, and cosmopolitan — not country. Yet, André 3000 and Big Boi did not mind being regarded as country; in fact, they embraced it.

Their music and Southern hip-hop overall incorporated the stylings of blues and gospel. Their delivery had a twang to it. They were not here to duplicate East Coast or West Coast hip-hop. They were on a mission to give young, Black, working-class people in the South something to say. Although based in Atlanta, their perspectives and reflections on Black life in the South took root in states across the region. Eventually, they became the leaders of the Southern hip-hop scene. So, when the duo won the GRAMMY for Album Of The Year, for Speakerboxxx/The Love Below, at the 2004 GRAMMYs — almost 10 years after their declaration at the Source Awards — the South was not only respected in hip-hop, but it became a contender for its rightful title. — Taylor Crumpton

Explore More: Deep 10: OutKast's Speakerboxxx/The Love Below

Public Enemy

One of the most profound and prolific groups in hip-hop's storied history, Public Enemy continues to be studied and applied to moments impacting music and culture today. Once Chuck D and Flava Flav connected with Terminator X and the Bomb Squad, the ethos and foundational tenets upon which hip-hop was founded — peace, love, unity, and having fun — finally came into realization. Their boom merged with the bap of the streets to showcase the reasons why hip-hop's culture should not only be championed but cherished — never allowing history to be erased or revised.

Members would go on to leave their imprint all over the then-burgeoning sound coming out of America. From producing Bel Biv Devoe's triple-platinum album, Poison, to contributing to one of the defining hip-hop albums of the 1990s, Ice Cube's AmeriKKKa's Most Wanted, Public Enemy has resonated through time as thought-proving and spark-inducing revolutionaries of sound that still challenge people to know that loud is not enough. — Kevin L. Clark 

Explore More: "Fight The Power": 7 Facts Behind Public Enemy's Anthem | GRAMMY Hall Of Fame

The Roots

The Roots' longevity and artistic creativity have made a lasting impact on hip-hop. Illadelph's own are trailblazers of the genre, pioneers of a distinctive, alternative sound that combined rap with live instruments, conscious lyrics and jazz-influenced beats.

The Roots have not been afraid to tackle important topics and challenge societal norms: The video for their song "What They Do," off their third album Illadelph Halflife, mocks stereotypes seen in the music industry. Their most successful album, Things Fall Apart, is a nod to Chinua Achebe's critically acclaimed book by the same name. The album originally had five different covers, one of which features teenagers running from police during the Civil Rights Movement era. The stark black-and-white image, alongside the album's themes, provided an artistic cohesion and political poignancy that solidified the group's impactful message. 

All told, the Roots have 14 studio albums under their belt. Aside from music, the group's career evolution spans various ventures, including publishing (Black Thought's upcoming memoir, The Upcycled Self), music festivals (the annual Roots Picnic festival), and film (Questlove's GRAMMY-winning Summer of Soul). Not to mention mainstream TV: The Roots also hold down late night as the house band for NBC's "The Tonight Show with Jimmy Fallon." The group's unique sound and its expression of pressing issues solidify the Legendary Roots Crew as important game-changers. — Rachel McCain

Explore More: On Things Fall Apart, The Roots Deepened Hip-Hop

Roxanne Shanté

Historically, hip-hop has always been heralded as a young person's sport — and perhaps no one exemplifies that archetype better than Queensbridge's Roxanne Shanté. At merely 14, the upstart member of the Juice Crew led one of hip-hop's first rap beefs, responding to the U.T.F.O.'s (Untouchable Force Organization) "Roxanne Roxanne" with the searing "Roxanne's Revenge." Where U.T.F.O. detailed the saga of a woman who rejected their overtures, Shanté rebutted with a sharply constructed counternarrative, freestyling a story from the viewpoint of Roxanne being pestered by inadequate suitors who paled in comparison to her MC skills.

While the initial response made her famous, it would be her unflappable ability to hold her own in the flood of response tracks that would cement her legacy as a battle rapper and recording artist. Tracks such as "Queen of Rox (Shanté Rox On)" and "Bite This" would extend her victory streak against U.T.F.O. and the bevy of opponents who stepped up to the plate as the city raced to cash in on the so-called "Roxanne Wars." When KRS-One crudely attacked her in "The Bridge is Over" — in which he declared, "Roxanne Shanté is only good for steady fucking" — she rebutted on "Have a Nice Day": "Step back, peasants, popping all that junk/Or else BDP will stand for Broken Down Punks/'Cause I'm an all-star just like Julius Erving/And Roxanne Shanté is only good for steady serving." Not only was Shanté able to best the guys at their own game, but she also made a point to embarrass their misogynistic attacks while doing so. Further etching her impact on rap, this legacy would echo through the ages to be reflected in the likes of Megan Thee Stallion and Noname, even finding a spiritual namesake in Nicki Minaj's 2010 single, "Roman's Revenge." — Shamira Ibrahim

Run-D.M.C.

With two MCs (Joseph Simmons, aka Run, and Darryl McDaniels, aka D.M.C.), one DJ (Jason Mizell, aka Jam Master Jay), and a whole lot of Adidas, Run-D.M.C. became one of hip-hop's earliest music and style ambassadors to the world. It only took a few years after their 1984 debut for fans across the globe to know about their New York hometown of Hollis, Queens.

In 1986, Run-D.M.C. collaborated with Aerosmith on a new version of the Boston rock act's 1975 cut "Walk This Way." The unexpected, groundbreaking pairing became a No. 4 hit on the Billboard Hot 100 chart. MTV put the song's music video, which shows the two groups literally smashing down walls, in heavy rotation and positioned the rappers as the genre-bending superheroes they're still seen as today, as their GRAMMY Hall Of Fame induction attests. 

Before there were hip-hop categories at the GRAMMYs, Run-D.M.C. was nominated for Best R&B Performance By A Duo Or Group With Vocal at the 1987 GRAMMYs for their 1986 album, Raising Hell. After releasing seven albums and starring in the seminal hip-hop movies Krush Groove and Tougher Than Leather, Run-D.M.C. became the first rappers to receive the Recording Academy's Lifetime Achievement Award, an honor they received in 2016.

After surviving decades of the world insisting that hip-hop was a fad that would fade away, the natural course of Run-D.M.C. was cut short when Jam Master Jay was killed in his Queens, New York, recording studio in October 2002. Unforeseen violence cut the band's physical life short, but Run-D.M.C. remains an immortal mainstay in the pantheon of hip-hop history, a blueprint for countless rap tandems, and an essential part of the culture. — Tamara Palmer

Scarface

There is no one quite like Scarface when it comes to this rap game. An innovator in rap subgenres like horrorcore and gangsta rap, he is one of hip-hop's most poignant storytellers and pioneers. Both as a member of the legendary Geto Boys — one of the most successful Southern hip-hop groups at a time when the spotlight was focused on East Coast and West Coast rap — and as a solo artist, he proved to be a last of a dying breed. His signature songs, like "I Seen a Die," off the five-mic, Source-certified classic album, The Diary, proved to listeners that there were more layers and depths to experience in rap.

As both a commercial chart-topper — his 1997 album, The Untouchable, reached No. 1 on the Billboard 200 chart — and the ear of the streets nationwide, Scarface helped establish Houston as a certified rap capital and an early hotbed for innovative independent record labels. Beloved by fans, students of hip-hop and critics alike, 'Face has showcased what it means to craft a complete body of work that stands exemplary above its predecessors. He is one of the best at making the mood move within the melody. Beyond his platinum- and gold-certified album successes, he also excelled at mixing business acumen with artistic vision: As president of Def Jam South in the early 2000s, he helped foster the career of Ludacris and other rising Southern rappers. Today, his continued influence reaches modern veterans like the Game and next-gen stars like Isaiah Rashad alike. — Kevin L. Clark

Snoop Dogg

Few music artists have showcased the versatility and decades-long career evolutions of prolific multihyphenate Snoop Dogg. Hailing from from Long Beach, California, his rap career took off in 1992 when his stepbrother Warren G, of "Regulate" fame, gave one of his mixtapes to Dr. Dre. Fresh off his stint with N.W.A, Dre recognized the young rapper's potential and invited him to the studio — where he was laying down tracks for The Chronic — for an audition. Snoop seized the moment and conquered: He's featured on 11 of the classic album's tracks, including the prolific hit single that would skyrocket him into the mainstream, "Nuthin' but a 'G' Thang."

Still going strong decades later, the influential rapper has sold more than 37 million albums worldwide and has dropped 19 studio albums and countless cross-genre collabs. Snoop's laid-back persona and distinctive West Coast slang have become hallmarks of his music career. His expansion into other business and artistic pursuits, which include films, fast-food takeovers, and TV shows with lifestyle guru Martha Stewart, and impact on his community are among the main reasons he's maintained cultural relevance across three decades.

Learn More: Essential Hip-Hop Releases From The 1990s: Snoop Dogg, Digable Planets, Jay-Z & More

While his list of musical achievements is staggering, Snoop's greatest contribution to hip-hop lies in his ability to authentically infuse elements of his life into non-musical spaces. By simply staying true to himself, the legendary rapper has helped to further legitimize hip-hop as an art form with global impact and recognition, simultaneously influencing the music industry and people across international borders. 

And he's even left his mark on the English language. Using his signature "izzle" style (e.g., "fo shizzle" meaing "for sure"), which originated in Northern California and was popularized by Bay Area rap acts like E-40 and 3X Krazy, Snoop has created a slew of catchy and memorable phrases. This rap "slanguage" development helped innovate distinct rap styles and solidified his place as an evolutionary icon. — Desiree Bowie

Soulja Boy

Soulja Boy made a lasting impact on hip-hop culture with his very first single. As one of the first in a wave of artists who used internet culture to market themselves directly to fans, the Chicago native created rap's first true internet sensation with "Crank That (Soulja Boy)." The song — fueled by simplistic lyrics, a catchy beat, and an inescapable hook — skyrocketed throughout the global internet via its complementary viral dance. Subverting the label-to-audience pipeline, Soulja Boy capitalized on tools like YouTube and MySpace to propel his popularity and connect with new listeners directly. Millions watched the song's music video on YouTube, where it has amassed more than 556 million views to date, and shared it widely on social media.

The innovative formula worked: "Crank That (Soulja Boy)" topped the Billboard Hot 100 chart for several weeks, set a record for the most digital downloads ever with more than 3 million units sold, and secured a GRAMMY nomination for Best Rap Song at the 2008 GRAMMYs.

Soulja Boy proved one-hit-wonder naysayers wrong. His second album, iSouljaBoyTellem, delivered 2000s classics like "Kiss Me Thru the Phone" featuring Sammie and "Turn My Swag On," while his grassroots tactic ushered in a new era of fan engagement and user-generated content, creating a formula still used by internet-savvy, next-gen artists like Lil Nas X and the wider music industry to market hip-hop hits today. — Victoria Moorwood

Timbaland

Virginia native Timbaland spent the mid- to late-'90s cultivating an experimental sound that blended futuristic drum patterns with unique sampling techniques. When he wasn't pushing sonic boundaries for R&B artists like Aaliyah and Ginuwine, the four-time GRAMMY winner proved his creativity could extend to hip-hop as well. 

There isn't a better example than his legendary run of genre-busting albums produced for fellow Virginian trailblazer Missy Elliott, including Supa Dupa Fly, Da Real World, Miss E… So Addictive, and Under Construction. Timbaland even helped usher in the country rap subgenre thanks to his production work on the hip-hop/bluegrass fusion album Deliverance from Bubba Sparxxx. Eventually, he would expand far and wide across genres to create mega-hits with pop artists ranging from Nelly Furtado to Justin Timberlake. Between that time, he continued working with legendary rappers, including LL Cool J, Jay-Z, Snoop Dogg, Ludacris, Lil' Kim, and many more.

Throughout the years, he's worked on multiple classic albums, which have garnered Album of the Year GRAMMY nominations, including Beyoncé, Timberlake's Justified and FutureSex/LoveSounds, The Diary Of Alicia Keys, and Elliott's Under Construction. Timbaland was also nominated for Producer Of The Year, Non-Classical at the 2008 GRAMMYs.

Now, Timbaland is making quality production easily available to aspiring artists and producers through his BeatClub service, showcasing how indispensible and intergenerational the creative mind of Timothy Mosley is to the culture. — Ural Garrett

Wu-Tang Clan

Wu-Tang Clan was one of rap's seminal groups, both for their impact in the booth and in the boardroom. Enter The 36 Chambers, their 1993 debut album, saw superproducer RZA unite nine of the most unique personalities in rap ever for a lightning-in-a-bottle explosion. The crew traded nimble-footed bars and pro-Black philosophies over a discordant combination of rugged beats and samples from martial arts flicks, with each voice and rhyme style completely different from the last. But after their call to arms, they revolutionized the game with their business empires: The Wu was the first group to have its members sign solo deals with varying labels.

From there, they brought new meaning to the term divide and conquer: RZA, GZA, Ol' Dirty Bastard, Inspectah Deck, Raekwon, U-God, Ghostface Killah, Method Man, Cappadonna, and Masta Killa would each go on to drop classic records over the years, all of them earning varying spots in the rap hall of fame. In subsequent decades, they'd reunite on occasion to duplicate the group magic in new and creative ways. 

After that, changing the game just became part of the Wu-Tang Clan playboook. Clothing lines, video games, TV shows — you name it and the Wu tried it, and likely surmounted it. In 2015, they created Once Upon A Time In Shaolin, a single-copy album that was sold off in an auction to a pharmacy exec for more than $1 million dollars … before that exec was arrested and imprisoned, with the record being seized by the government in the process. Oh well. Wu-Tang Clan has made history plenty of times, and before all is said and done, they'll likely do it again. — William E. Ketchum III

Explore More: Dissecting the Chambers: Wu-Tang Clan's Debut Opus Turns 25

Honorable Mentions:

The below is a list of artists who we'd like to celebrate in addition to the artists featured in our 50 Artists Who Changed Rap list. Submitted by our industry panel, these honorable mentions have impacted hip-hop in ways that are immeasurable.

• Beastie Boys

• Big L

• Big Pun

• Busta Rhymes

• Cardi B

• DJ Premier

• DJ Quik

• DMX

• Fugees

• Geto Boys

• Grandmaster Caz

• The Hot Boys

• Hype Williams

• Ice Cube

• J. Cole

• Juvenile

• Kid Cudi

• KRS-One

• MC Lyte

• Nelly

• Prince Paul

• Queen Latifah

• Redman

• Salt-N-Pepa

• Schoolly D

• Three 6 Mafia

• Twista

• UGK

• Ultramagnetic MCs

• Wiz Khalifa

Industry Panel:

The artists featured on GRAMMY.com's 50 Artists Who Changed Rap list were compiled from artist submissions submitted by an industry panel of rap experts, which includes:

• Andrew Barber, Owner, Fake Shore Drive

• April Reign, Senior Advisor for Entertainment & Media, Gauge

• Carl Chery, Creative Director, Head of Urban, Spotify

• Datwon Thomas, Editor-In-Chief, VIBE

• Jeff Weiss, Editor, Passion of the Weiss

• Jeff and Eric Rosenthal, Co-owners, ItsTheReal

• Justin Hunte, music360 journalist, BTSN

• Justin Tinsley, Senior Sports and Culture Reporter, Andscape

• Kathy Iandoli, Author of ‘God Save The Queens: The Essential History of Women In Hip-Hop’ and co-author of ‘Lil' Kim's The Queen Bee’

• Kevin L. Clark, Subject To Change LLC, Producer / The Recording Academy/GRAMMY.com, Contributing writer

• Mankaprr Conteh, Cultural Journalist and Rolling Stone Staff Writer

• Meka Udoh, Co-founder, 2DopeBoyz / Ingrooves Music Group

• Miles Marshall Lewis, Author

• Naima Cochrane, Music & Culture Journalist

• Roderick Scott, Vice President, Marketing Strategy, Republic Records

• Shaheem Reid, Legendary journalist

• Shamira Ibrahim, Culture writer & critic

• Shawn Setaro, Freelance Writer and podcaster

• Sowmya Krishnamurthy, Author of ‘Fashion Killa: How Hip-Hop Revolutionized High Fashion’

• Ural Garrett, Freelance Journalist

• William E. Ketchum III, Music & Culture Journalist

• Yoh Phillips, Documentarian/music journalist, Rap Portraits

• Zini Tahsini, Hip-Hop Editorial Programmer, Apple Music

Production Credits:

GRAMMY.com's 50 Artists Who Changed Rap list was conceived and developed by:

• John Ochoa: Managing Editor of Digital Media for the Recording Academy

• Kevin L. Clark: longtime GRAMMY.com contributor, hip-hop tastemaker, screenwriter, and founder of Love, Peace & Spades, a rather fly game night series

• Len Brown: Senior Project Manager of Awards and Rap, Reggae, and R&B Genre Manager for the Recording Academy

6 Artists Expanding The Boundaries Of Hip-Hop In 2023: Lil Yachty, McKinley Dixon, Princess Nokia & More

Rap albums of the 1990s showcased diverse sides of the hip-hop landscape, broadening both the sound of the underground and hits of the mainstream. By the 2000s, reigning hip-hop artists were either reinventing themselves —  among them, Jay-Z, Nas, Snoop Dogg and Lil' Kim — or giving way for up-and-comers. 

The 2000s hip-hop held space for rappers entering different phases of their careers, from luxuriant to conscious. Most 2000s hip-hop soundtracked a rowdy decade-long party, where Timbaland became a sought-after beatmaker for his experimental sounds, and the Neptunes’ synthetic production made them dominate radio play. Rappers continued to retell their rags to riches stories, while celebrating the fruits of their labor. 

A creative streak permeated throughout the decade, creating new styles and geographical hotspots. While the East, West Coast and Midwest held down their rap enclaves, hip-hop’s core largely went below the Mason-Dixon line, giving cities such as New Orleans, Atlanta, Houston and Miami well-deserved respect in the game. 

In the 2000s, different sectors of entertainment wanted to cash in on hip-hop's ever-growing traction. Hood films of the ‘90s evolved into heists (Paid In Full), biopics (8 Mile) coming-of-age stories (ATL) and dance flicks (Honey), many which had rappers taking their first acting roles. These new faces of Hollywood were also even tapped to star in TV advertisements for the likes of Nike and Sprite, the latter which has championed hip-hop for over 35 years. At the same time, a diamond-encrusted bling redefined hip-hop style, and several artists helmed self-established streetwear brands. 

Most importantly, the music kept spinning, turning hip-hop into a free-for-all playground that grew more inclusive as the years rolled on. While hip-hop’s golden age had undoubtedly ended, the 2000s saw the ascension of now-household names whose music is now being reworked by Gen-Z rap and pop artists. Here are 10 albums that captured hip-hop’s growing diversity and influence in music in the first decade of the new millennium. 

Nelly - Country Grammar (2000)

The East vs. West Coast cataclysm took over in the late 1990s, but the Midwest waved its flag high in the Y2K era. St. Louis-raised Nelly unapologetically recited nursery rhymes and dished out heartland twang on his seminal debut Country Grammar. Bringing local culture to the masses, Country Grammar catapulted Nelly into megastardom, as the album topped the Billboard 200 in its first week.

Cornell Haynes Jr., Nelly would forgo his baseball dreams when"Country Grammar (Hot S—)" ran hip-hop airwaves. A consistent run of hits followed: party-starter "E.I.," the hoedown-worthy "Ride Wit Me," and the "The Jeffersons"-dedicated "Batter Up," which featured Nelly’s side project, St. Lunatics. The rapper’s commercial appeal made him an instant favorite for kids and club-goers, both who raved over Nelly’s sing-a-long music. Nelly gave the world a glimpse of his "derrty" character, solidifying him as an early 2000s rap mainstay. 

Missy Elliott - Miss E... So Addictive (2001)

If Missy Elliott's Supa Dupa Fly and Da Real World were the one-two punch of the late ‘90s, those releases were also a prelude to her most globally successful album. Elliott  sent her progressive sound out of the stratosphere on her third album Miss E… So Addictive. Hypnotic, authentic and brilliantly innovative , So Addictive imagined spaced-out hip-hop and R&B scenes that fans could revel in. 

Timbaland-produced lead single "Get Ur Freak On"—which heavily used elements of non-traditional Punjabi music Bhangra — burned up dancefloors worldwide and won a GRAMMY for Best Rap Solo Performance in 2002. The near-misandrist bedroom banger "One Minute Man" shamed weak male lovers while Elliott and Ludacris asserted their sexual dominance. 

So Addictive dropped just months before the death of Aaliyah, Elliott’s longtime friend and collaborator. Elliott later dedicated the downtempo ballad "Take Away" to the late 22-year-old. Elliott’s most experimental LP yet made her a powerhouse that never ran out of off-the-wall ideas.

Eminem - The Eminem Show (2002)

Already a superstar due to 1999’s The Slim Shady LP and 2000’s The Marshall Mathers LP, The Eminem Show gave the Detroit native the title of the highest-selling rapper of all-time. The album would even earn two GRAMMY Awards, one for Best Music Video ("Without Me") and another for Best Rap Album.

For his fourth studio album, the Real Slim Shady went rogue. Hip-hop needed "a little controversy," EM rapped on lead single "Without Me," offering the middle finger to sensationalized celebrities and political figures. Zany and comedic in nature, "Without Me" spoofed impressionable suburban kids and Electronic musician Moby. 

Yet The Eminem Show offered more than just shock value. On "White America," Eminem acknowledged that his commercial appeal was partially due to being a white rapper. He continued confronting his problematic childhood, troubled relationship with his mother and faults on the cathartic "Cleanin’ Out My Closet." 

"Sing for the Moment,"  which interpolated 1973 Aerosmith classic "Dream On," garnered more radio play while harkening back to Eminem's impoverished upbringing and rocky start to fatherhood. As Eminem was just six years into his career, The Eminem Show was a lightning rod in a continued streak as a polarizing artist.

Clipse - Lord Willin’ (2003)

Missy Elliott wasn’t the only Virgina-bred rapper who reigned during the 2000s. Virginia Beach rhymesayers Pusha T and No Malice, known jointly as Clipse, rode high on their major label debut Lord Willin’. An early act on the Neptunes’ record label Star Trak Entertainment, Lord Willin’ predestined the legacy of the twin brothers.

Bars of fury flew throughout the regional statement album, ensuring that lunchroom tables would never be the same when lead single "Grindin’" released. The song’s table-beating and locker-slamming nature recalled high school cypher nostalgia, while Clipse boasted of their hustle mentality. 

Pharrell Williams (one half of the Neptunes) acted as Clipse’s hype man with adlibs and memorable hooks throughout the album. Faith Evans belted on "Ma, I Don’t Love Her," where Clipse pleaded for their significant other to avoid messy dating gossip. Club banger and MTV favorite "When’s the Last Time" still brought the wordplay, as Pusha T cleverly referenced a legendary 1980s crooner ("What did it, the whip appeal or my baby face?").

Both in the zone, Clipse made their mixtape rap flair a crossover smash. The brothers, who would shut down ComplexCon for the LP’s 20th anniversary, continue to salute their groundbreaking debut during rare performances, the next being IQ/BBQ in Queens.

50 Cent - Get Rich or Die Tryin' (2003)

Queens titan and Eminem protégé 50 Cent brought hip-hop to its knees with his 2003 debut, daring critics to test his gangsta. Get Rich Or Die Tryin’ debuted at No. 1 on the Billboard 200, just three years after 50 Cent recovered from being shot nine times. Over 19 tracks, the G-Unit frontman retold his story of victim to villain. 

The former Jam Master Jay protégé kicks down the door on "What Up Gangsta," and denies being anyone’s Superman ("They say I walk around like I got a S on my chest / Nah, that's a semi-auto and a vest on my chest."). He keeps his enemies close and depicts near-death experiences on "Many Men (Wish Death)." The rapper showed his affectionate side on "21 Questions," where he probes his partner’s loyalty. He flosses his extravagant lifestyle on the steel pan-tinged "P.I.M.P.," which was customary to blinged-out artists of the 2000s. 

The album’s biggest single, "In Da Club," made a resurgence when 50 Cent was a surprise guest during the Dr. Dre-curated Super Bowl LVI halftime show in 2022. 50’s brief spot during the performance paid homage to his "In Da Club" music video, where his bold entry into hip-hop paved the way for his East Coast rap successors to reclaim the streets.

Outkast - Speakerboxxx/The Love Below (2003)

Atlanta rap forerunners Outkast brought quintessential funk to their fourth studio album. Released as a double album — where Big Boi’s Speakerboxxx boomed and André 3000 opened up his innermost romanticism on The Love Below  — each record highlighted the duo’s individualism. 

Big Boi gave a masterclass in rhyme and flow on Speakerboxxx, exuding a warmth that made songs like "The Way You Move," "Bowtie" and "The Rooster" playlist selections for summertime gatherings for years to come. The nightmarish "Bust" featuring fellow ATL emcee Killer Mike references a mid-’70s era George Clinton. The electronic production on "Tomb of the Boom" is the perfect freestyle backdrop for Boi to trade verses with  rap trio Konkrete, fellow Dungeon Family member Big Gipp and Ludacris.

3000 demonstrated his multi-hyphenate chops, acting as singer/-songwriter, rapper, producer and maestro on The Love Below. He falls into lustful temptation on the Prince-inspired "Spread" before finding his close-to-perfect match ("Prototype"). An Outkast reunion takes place on the soulful "Roses," where 3000 wails about a snobby "Caroline." Karaoke staple "Hey Ya!" invented whimsical and now-classic lines like "What’s cooler than being cool? (Ice Cold)" and "shake it like a Polaroid picture." 

Speakerboxxx / The Love Below preceded Outkast’s 2006 musical film Idlewild, which reinterpreted select songs, and the album scored three GRAMMY Awards in 2004, including the coveted Album of the Year. By 2004, Outkast approached their hiatus, which has continued albeit a brief music festival run in 2016.

T.I. - King (2006)

Titled after the rapper’s fifth child, King made a statement that T.I. had the "top spot," as declared on DJ Toomp-produced lead single "What You Know" (which also won a GRAMMY Award for Best Rap Performance in 2007). The album was a perfect cross-promotion with T.I.’s acting debut in the comedy-drama ATL, which arrived in theaters just days after the release of King.

T.I. recruited top hip-hop producers from all coasts to bring their best to his fourth studio album. The effort paid off, as Alabama’s Kevin "Khao" Cates reimagined Crystal Waters’ 1991 deep house anthem "Gypsy Woman (She's Homeless)" on "Why You Wanna." Bronx-born superproducer Swizz Beatz brought out the sirens on the marching band sounds of "Get It." The piano-laden "Goodlife" featuring Common was courtesy of the Neptunes, with Pharrell Williams providing the song’s hook. 

Whilst calling out his competition, the self-appointed King of the South came to the game with nothing left to prove.

Kanye West - Graduation (2007)

In 2007, Kanye West and 50 Cent went head-to-head over first week sales. The two were well into their respective careers, but the friendly rivalry went public, including a competitive Rolling Stone cover shot. 

But West would win the war, amassing 957,000 in first-week sales and earning the No. 1 spot on the Billboard 200 for his third studio album Graduation. Exploring more sonic ground, Graduation marked an end to West’s alt-rap heyday.

The Chicago-raised artist aired out his frustrations on "Stronger," which expertly sampled the 2001 Daft Punk single "Harder, Better, Faster, Stronger." The synthy and anthemic "I Wonder" finds West reaching his hip-hop dreams. The rapper gives a shout out to "Summertime Chi" and flaunts his riches on the head-knocking "Good Life." Barely escaping the clutches of a vengeful ex, "Flashing Lights" shows a more vulnerable West, who admits his relationship flaws. 

West’s final Graduation Bear era would earn him two GRAMMY Awards in 2008, in the categories of Best Rap Song ("Good Life") and Best Rap Album.

Lil Wayne - Tha Carter III (2008)

New Orleans lyricist Lil Wayne conquered mainstream hip-hop with his sixth studio album, Tha Carter III. In lieu of guest appearances and frequent mixtapes, Wayne challenged Jay-Z’s "best rapper alive" status while boasting features with some of R&B’s elite players. In fact, Wayne nabbed Jay-Z for  the chipmunk soul of "Mr. Carter," titled after the pair’s shared last name (no relation). 

The daring move paid off, as TC3 won GRAMMY Awards for Best Rap Album, Best Rap Solo Performance ("A Milli") and Best Rap Song ("Lollipop"). Hip-hop’s top hook singer of the mid-2000s, T-Pain, contributed his auto tuned vocals to the frenzied "Got Money." Bobby V’s absurd police car sounds coated "Mrs. Officer," where Weezy shows his affections for women in uniform. 

His agile rhyme schemes run rampant throughout the album, notably "Phone Home," where he proclaims "we are not the same, I am a martian." TC3 proved that Wayne was surely from another planet, and the rapper continues to demonstrate that he’s inimitable.

Kid Cudi -  Man on the Moon: The End of Day (2009)

Kanye West walked so Kid Cudi could run. Both hedonistic and conscious, the Cleveland rhymer marched to his own drum on Man on the Moon: The End of Day. Split into five acts, MOTM hazily conceptualized Cudi’s path to inner peace. 

Production that ranged from psychedelia to synth-pop also made the rapper distinct from his peers in the blog era of rap. Arguably the most memorable track, the diamond-certified "Pursuit of Happiness (Nightmare)" played as an electronic rap midnight jam session with collaborators MGMT and Ratatat. 

"Soundtrack 2 My Life" detailed Cudi’s mental health woes and the death of his father. The minimal ambience of "Day ‘N’ Night" saw Cudi taking shape as "The Lonely Stoner," who uses medication to escape depression. Despite Cudi’s bleak outlook on life, he gave space to his "wildest dreams" on "Enter Galactic (Love Connection, Pt. 1)," which later titled his 2022 Emmy-nominated animated Netflix special. 

MOTM gave way to a forward-thinking side of hip-hop, where rappers could ambitiously experiment with a multitude of genres. Cudi's fans include Travis Scott, Chance the Rapper and A$AP Rocky, each of whom followed Cudi's example in distinct ways.

Essential Hip-Hop Releases From The 1990s: Snoop Dogg, Digable Planets, Jay-Z & More

Three decades ago, hip-hop made a turn from the underground to commercial fanfare. The eclectic sensibilities of the 1980s created space for artists of all stripes, leading to the golden age of hip-hop, and releases that are now considered an integral part of the genre's canon. By the 1990s hip-hop was a chart-topping entity and enterprise, where artists were popularized through streetwear campaigns and brand deals.

In this decade, rappers were multifaceted in their flow and lyrics — whether rugged and hard-spitting, or poetic and fervently expressive. Artists like psychedelic hip-hop group De La Soul, salacious femcee Lil' Kim and Atlanta heavy-hitters Outkast expanded rap’s palette. Beats ranged from synthetic to weighty 808 drum patterns, all which redefined the genre’s 20-year presence. 

Hip-hop chronicled truth and fantasy, providing listeners both deeply resonant and vividly divergent soundtrack whose influence continues to be felt. Decades later, records released in the 1990s are legend, and many of them appeared on the 65th GRAMMY Awards stage in a massive tribute to hip-hop.Here are 10 signature albums that bridged the golden age and the digital era of hip-hop.

De La Soul - De La Soul Is Dead (1991)

By 1991, conscious hip-hop pioneers De La Soul were over the "D.A.I.S.Y. Age" introduced on their seminal debut album 3 Feet High and Rising. The Long Island trio, composed of Posdnuos, Maseo and the late Trugoy the Dove jazzed up their sound on sophomore effort De La Soul Is Dead, marking a radical transition from hip-hop "hippies" to earnest rhymesayers. 

Posdnous and Trugoy melded simple production (courtesy of Prince Paul) with complex bars on "Pease Porridge," and also explored the traumas of sexual molestation through metaphor on "Millie Pulled a Pistol on Santa." Although De La Soul Is Dead received mixed reviews, the LP was one of the first albums to earn a five-mic rating in hip-hop publication The Source. "Still progressing and proud of it, De La has successfully escaped being trapped in the sophomore jinx with grooves that are harder than a brick wall," the throwback review reads.

With De La Soul Is Dead, the group, whose back catalog just arrived on digital music services in March, evaded the dreaded sophomore slump and cemented their place in hip-hop history.

Snoop Dogg- Doggystyle (1993)

After Calvin Broadus — then performing under the moniker Snoop Doggy Dogg —  released his breakthrough album Doggystyle, West Coast rap was never the same. Playing on inspirations from classic Blaxploitation films and early funk pioneers, Snoop kept his posture smooth while rhyming over beats from Dr. Dre (who also discovered the Long Beach native), and welcomed fellow then-newcomers like The Lady of Rage, Tha Dogg Pound, Warren G and RBX as features.

Giving listeners "just a small introduction to the G-Funk era," Snoop helped usher  in a soul-laden gangsta rap  sound that stood in distinct contrast  to the East Coast’s grittiness and jazz influence. The iconic "Gin and Juice" and "Who Am I (What’s My Name?)" have long been summertime cookout staples, while the eerie "Murder Was the Case" preceded Snoop being acquitted of murder just three years later. Now a 16-time GRAMMY nominee, Doggystyle marked Snoop’s debut as a hip-hop elite.

A Tribe Called Quest - Midnight Marauders (1993)

Three albums into their career, A Tribe Called Quest didn’t let up on Midnight Marauders. The Queens-bred group, which included Q-Tip, the late Phife Dawg, Ali Shaheed Muhammad (and occasional member Jarobi White) flaunted their lyricism and expansive musical knowledge  on the 1993 release, which was navigated by a robotic "tour guide."

Q-Tip and Phife’s wordplay is nimble throughout the album, but truly spotlighted on the Trugoy the Dove-assisted "Award Tour," the amorous "Electric Relaxation" and "The Chase, Pt. II." "8 Million Stories" and "Midnight" were solo moments for Phife Dawg and Q-Tip, respectively, each who had brushed up their penmanship since ATCQ’s 1991 reinvention on The Low End Theory. Both atmospheric and imaginative, Midnight Marauders showcased ATCQ’s range as a progressive hip-hop act.

Digable Planets - Blowout Comb (1994)

Jazz rap trio Digable Planets maintained their cool just one year after winning a GRAMMY Award for Best Rap Performance By A Duo Or Group. In 1994, Ishmael "Butter Fly" Butler, Mariana "Ladybug Mecca" Vieira and Craig "Doodlebug" Irving followed with Blowout Comb, their second and final studio album. With a minimalist approach, Digable Planets trekked through urban and Afrocentric themes soundtracked by live instrumentation and spoken word.

Emotionally stirring and thematic, "Black Ego" saw Digable Planets tackling economic injustices and Black nationalism with nods to Blaxploitation films Cleopatra Jones and Superfly. The group asserted their refusal to go commercial on laidback earworm "Jettin." Seventies slang and references to New York City boroughs floated throughout Blowout Comb, and although singles "9th Wonder (Blackitolism)" and "Dial 7 (Axioms of Creamy Spies)" didn’t chart, the album reintroduced Digable Planets in their most authentic form and reached No. 32 on the Billboard 200.

2Pac - Me Against the World (1995)

With an awareness unrivaled by his  contemporaries, Tupac Shakur's penultimate album, Me Against the World, exploredhis complexities. By March 1995, the rapper had served one month in prison on sexual abuse charges, and had used his previous year of freedom to record arguably the most poignant LP of his lifetime.

On the titular track, Shakur examined impoverished Black communities and morbid thoughts of mortality. A sample of Stevie Wonder’s "That Girl" textures "So Many Tears," where 2Pac vocalizes music industry woes, his depression and even predicts an early death. "Dear Mama," (which inspired the FX docuseries of the same name), was 2Pac’s dedication to mother and former Black Panther Party member Afeni Shakur; it became the third song by a rap act to be placed in the Library of Congress.

The latter song and Me Against the World would both earn Shakur his first GRAMMY nominations. While he didn't win, both are masterpieces that signaled the rapper’s coming-of-age.

Jay-Z - Reasonable Doubt (1996)

Jay-Z gave a solid lyrical offering on his 1996 debut. A landmark album on the now-defunct Roc-A-Fella Records, the 14-track Reasonable Doubt brought mafioso and luxury rap into the ring, as Jay-Z gave semi-autobiographical tales of street life.

On "Feelin’ It," the Brooklyn rapper boasts his riches and opulent lifestyle, while the Issac Hayes-sampling "Can I Live" explores the close calls that the hustle brings. Hov’s stream-of-conscious flow highlighted production from the likes of Ski Beatz, DJ Premier and Clark Kent. 

Reasonable Doubt predicted Jay-Z’s thriving future without a doubt, as he’s since taken hip-hop’s throne as a coveted 24-time GRAMMY-winning artist (in addition to 88 nominations).

Lil’ Kim - Hard Core (1996)

Brooklynite Lil’ Kim carved out space for risque rap on her 1996 solo breakout Hard Core. Less than six months after the murder of her mentor the Notorious B.I.G., the former Junior M.A.F.I.A. member achieved solo commercial success for her provocative lyricism and appearance. Whereas many of her contemporaries adopted a more androgynous style, Lil’ Kim played up her sex appeal onstage and on record.  

The raunchy "Big Momma Thang," which samples 1978 Sylvester deep cut "Was It Something That I Said," shows Lil Kim’s allyship with queer listeners. Lil’ Kim asserted her hood dominance on "No Time," while flaunting her affection for being classily "draped in diamonds and pearls." Although Hard Core was Moderately received, Lil’ Kim’s rap successors —Doja Cat, Megan Thee Stallion and Cardi B — would later speak highly of the Queen Bee’s NSFW magnetism. Nearly 30 years later, contemporary women in hip-hop continue to strive for Lil’ Kim’s unapologetic influence.

Missy Elliott - Supa Dupa Fly (1997)

Hip-hop hadn’t witnessed fly until Missy "Misdemeanor" Elliott stepped onto the scene. The Virginia-born rapper and singer/songwriter had once been a part of R&B group Sista before partnering with producer Timbaland. The two both wrote and produced almost the entirety of Aaliyah’s 1996 album One In A Million. By the late ‘90s, Elliott’s pen was in demand, giving her the confidence to share her unconventional sound and look as a solo act.

Her 1997 debut, Supa Dupa Fly, redefined what it meant to be a woman in rap. Over Timbaland's bass-thumping production, Elliott went full-on futuristic. She humorously teased her sexuality on the audacious "Sock It 2 Me," while the bouncy "The Rain (Supa Dupa Fly)" sampled Memphis soul vocalist Ann Peebles with peculiar lyrics like "my finger waves these days, they fall like Humpty." 

Two decades before being inducted into the Rock & Roll Hall of Fame and receiving the Black Music Collective's Recording Academy Honors award, Elliott took the rap world by storm. Ahead of its time yet heralded, Supa Dupa Fly and Elliott’s one of a kind style showed the artist’s peers and successors how to be creative anomalies.

Outkast - Aquemini (1998)

The South had something to say on Outkast’s third album Aquemini. The duo of André 3000 and Big Boi asserted their southern charm and immaculate rhyme schemes on the 16-track album that catapulted them to stardom. As the two rappers perfected their individualism, Aquemini also showed 3000 and Big Boi seamlessly meshing their styles together.

More spacey than their sophomore album ATLiens, Outkast doubled up on their down home twang on the funky (but controversial) "Rosa Parks." The two questioned reality from dystopian technology on the surreal "Synthesizer" with P-Funk legend George Clinton. Listeners can visualize a juke joint scene on the reggae-tinged "SpottieOttieDopaliscious," where 3000 and Big Boi intertwine tales of a violent nightclub encounter and a cursed romance. 

Aquemini ushered a turn in Dirty South hip-hop, where the region gained national respect for its storytelling, realism and unique flow.

Dr. Dre - 2001 (1999)

Super producer and rapper Dr. Dre brought out the all-stars on his 1999 sophomore solo album 2001. The LP reunited the now seven-time GRAMMY-winner with his prodigies Snoop Dogg, Eminem, Xzibit, Nate Dogg and Kurupt, while ushering in a new age of West Coast rap. Seven years after his groundbreaking debut album The Chronic, the former N.W.A. member was "Still D.R.E."

On the aforementioned track, written entirely by Jay-Z, Dr. Dre flexed his near 15-year impact in hip-hop. "The Watcher" detailed the Compton native reaching music industry plateaus despite paranoia of "a new era of gangstas." Strip club anthem "The Next Episode" harkened back to Dre and Snoop’s "Nuthin’ But A 'G' Thang," while "Let’s Get High" captured a raunchy house party. On 2001, now certified 6x platinum, Dr. Dre was at his most carefree while setting the bar high for a new generation of hip-hop.

Essential Hip-Hop Releases From The 1980s: Slick Rick, RUN-D.M.C., De La Soul & More

Lil Nas X became a global sensation practically overnight, but it wasn't an accident.

The American singer and rapper — born Montero Lamar Hill — became fluent in music and pop culture at an early age, becoming a meme aficionado. His love for internet culture cultivated the perfect recipe for his debut single, "Old Town Road," to become one of the most viral hits in music history; the song also prompted a necessary conversation about the bounds of genre. 

"Old Town Road" rose to the top of the Billboard Hot 100 chart, and still holds the record for most time spent at No. 1 at 19 weeks. The single later helped Lil Nas X snag two GRAMMY Awards for Best Pop/Duo Group Performance and Best Music Video. (To date, he's won 2 GRAMMYs and has received 11 nominations overall.)

Aside from his immense musical talent, Lil Nas X — who came out as gay on social media during his Hot 100 reign — has been a fierce champion for LGBTQIA+ and Black communities.

"It's just acceptance of gay people. And they see that as a bad thing, like, They're trying to normalize it. You know what? Yeah. That's actually what I'm trying to do," he told GQ in 2021.

At just 24 years old, Lil Nas X has plenty more history-making and game-changing moves in store. As he revealed during his March 2023 campaign with Coach, "My next big chapter is coming."

Press play on the video above to learn more about Lil Nas X's industry-altering career, and check back to GRAMMY.com for more new episodes of Black Sounds Beautiful.

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