An American standard originally composed in 1959, "The Best is Yet to Come" has been recorded by an array of vocal greats, including Tony Bennett, Michael Bublé, Bob Dylan, and Ella Fitzgerald — the latter of whom won a GRAMMY for her rendition in 1984. But it's most closely associated with Frank Sinatra, who recorded it with jazz pianist Count Basie for their 1964 album, It Might As Well Be Swing. In fact, the song was so important to Sinatra that its titular lyric is carved into his tombstone.

In this episode of ReImagined, vocalist and cabaret-style performer Judy Whitmore delivers a faithful, buoyant rendition of "The Best is Yet to Come." A full orchestra performs behind her, including horns, jazzy drums, a sweeping string section, and a grand piano — creating a swinging performance that does Sinatra proud.

Whitmore's cover choice is no coincidence, as the singer has been inspired by American classics literally since birth — her namesake is legendary actor and musical performer Judy Garland. Like Garland before her, Whitmore has taken on a diverse and multifaceted career. She's a bonafide Renaissance woman, whose resume includes accomplishments as a theater producer, best-selling author and pilot, who also happens to have a Master's degree in clinical psychology.

Singing has been a lifelong passion for Whitmore, and she has several albums to show for it, including 2020's Can't We Be Friends. That project, which includes her spin on standards like "'s Wonderful," "It Had to Be You" and "Love is Here to Stay," is Whitmore's "love letter to The Great American Songbook," her website explains. 

"This is the music I grew up with, and I don't want people to forget it," she details. "I think it's one of the most extraordinary bodies of work ever created."

Press play on the video above to watch Whitmore bring her love of American classics to her version of "The Best is Yet to Come," and keep checking back to GRAMMY.com for more episodes of ReImagined. 

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Why is jazz so walled off to younger people? Laufey spends a lot of time pondering this question. And part of it comes down to the ways Gen Z might second-guess themselves.

"Like, how do you consume jazz music?" the Icelandic singer asks GRAMMY.com rhetorically. "Do you go to a jazz club? Do you have to be 18? Do you have be 21? When do you clap? How do you dress?

"There are so many barriers to entry," adds the 24-year-old, mononymous artist, whose full name is Laufey Lín Jónsdóttir. "It seems like something that's for an older, more refined, more educated set of society."

Which is something of a tragedy for music — especially given that youngsters made some of its most resonant works, and that much of jazz was meant for everybody. With that in mind, Laufey isn't out to shove the music down people's throats. She wants to leave them Bewitched.

That's the title of Laufey's second album, due out Sept. 8. Characterized by a more laid-back, accessible approach than its predecessor — 2022's Everything I Know About Love — the set is charming and companionable, from "Dreamer" to "From the Start" and its twilit, cinematic title track.

Read on for an interview with Laufey about her approach to Bewitched, the foundational influences of Astrid Gilberto and Chet Baker, and dismantling the wall between the youth generation and America's Music.

This interview has been edited for clarity.

Tell me how your creative evolution led to Bewitched.

I like to think it was written between Los Angeles and London — New York too, but mostly between those two places. And I touched a lot on that in the lyrics. This is my second album [and]  a return to my musical roots. I'm really leaning deep into my jazz and classical roots.

For my first EP [2021's Typical of Me] and album, I always had this goal and dream of bringing jazz music back to my generation. I hadn't seen many examples of doing that. So, I was just kind of seeing how far I could take it — how far I could go into jazz without scaring off Gen Z.

What I found after my first album was that the fans seem to mostly drift toward the songs that resembled jazz standards — ones that were recorded with a symphony orchestra. So, for this album, I had the confidence to just jump straight into that, with no fear that I would lose Gen Z.

The singles that have come out have been some of my most organic music, in that sense. And it's been the most well-received, which is really wonderful. It's such a great sign that music is moving in a direction where I can just be anything.

It's a love album, and touches on everything between love and heartbreak. My last album was a little bit hopeless romantic: Oh, I'll never fall in love. And this one's kind of like, OK, I'm learning a little more about love.

It's a shame how marginalized, niche and walled-off jazz can be. It's one of my greatest pleasures in life.

I mean, that's the whole reason I'm doing this.

But Gen Z might offer light at the end of the tunnel. Where does jazz sit within your age group?

I think there's been a space via social media, like TikTok. In the past few years, there's been so much more music introduced, because it's kind of introduced to you without you seeking it out.

I think Gen Z is a generation of really, really open-minded individuals, especially when it comes to music. I've found that friends and kids this age will listen to anything, really, as long as they can find some sort of line of relatability. That's what they care about.

Even though I'm writing songs that sometimes sound like old jazz standards, the lyrics are very modern; they're my personal experiences from this day and age. I think that relatability is what connects young listeners.

I started this project during Covid, and I found people wanted to find an escape from this bleak reality. We all had to stay home from high school and college; I graduated online, from Berklee.

I think we just wanted to be reminded of a time that wasn't masks and Zoom and whatever. Our escape was kind of found through music. My brainchild during that time was this kind of cinematic, jazzy landscape of music that felt like it didn't belong to 2020. It belonged to a different time.

Bewitched album art. Photo: Gemma Warren

Tell me more about how Bewitched reflects your roots. I'm sure there are all kinds of subliminal reflections of the music you love.

I have a jazz standard on the album, "Misty," that I referenced a couple of times on my first album.I wanted to do it in the most classic way, and we recorded it live in one take with a trio.

I'm a huge Chet Baker fan. Even in the first single off the album, "From the Start," I'm borrowing some Chet Baker licks in the scatting.

I grew up playing cello; my twin sister plays violin on it as well. There are a lot of classical influences that I dug into — a lot of Ravel and Mendelssohn and Ravel and Dvorak, which is really fun to hide in there. Because if you know, you know — and if you don't, it's just a fun, new treat.

Back to the Chet Baker point, the way that he sings is kind of like a trumpet. I really took on more of that vocal style on this album — more held back. I used to think [in terms of] vibrato and legato, and I still do, but I think I really [wanted] to emphasize the lyric and storytelling.

This style of singing that's a little more spoken word, a little more bossa nova — I think that really lends well to the songwriting. Bossa nova was also a big influence on this album.

I love Astrud Gilberto a lot; there's this [1967] album of hers called Beach Samba that I was really, really inspired by, specifically in "From the Start."

I'm obsessed with Chet Baker. Can you talk about him more?

Chet Baker is probably the reason I started creating my own music, and writing my own music. I fell in love with his interpretations two or three years ago, and listened to the entire discography.

The way he phrases — the way he approaches words, but also solos — I have completely taken that into my own kind of musicality.

I think it's because [Baker is] really approachable jazz music for Gen Z and new listeners. I think I would have been very scared to say that back in the day, when I was at Berklee. But I'm not afraid to say it now.

When my friends ask me, "What jazz musician should I listen to?" I'm always like, "Go listen to Chet Baker," because I think it's such a great way to introduce new listeners to jazz. Because he's not only a singer — he's a musician. He plays  jazz like a jazz musician.

His early vocal albums were my first immersion in the Great American Songbook. "I'm Old Fashioned," "You're Driving Me Crazy"...

And he doesn't mess with them too much. Which is such a great way to get to know these standards, but also understand jazz form. I love Chet Baker; I think he's just the greatest musician of all time.

On the cover of Chet Baker Sings It Could Happen To You, he's sitting underneath a [waxing crescent] moon. I almost did that for the album cover.

It's important to note these are original compositions, not interpretations. Tell me how you inhabited that language, to write something that feels part and parcel with jazz tradition.

Well, I've learned pretty much every jazz standard — the ones that are in the Real Book, the main ones. I've learned the lyrics; I've figured out the chords.

I think once you have that musical language within you and you understand the form a bit,  you'll find that jazz songs have a very similar form. There are lots of similar chords — the II-V-Is, which is my trick to make any song sound jazzy.

The songs on the album that are the most pop/rock-driven are climbing in II-IV-Is, which bring them back to jazz land — or Laufey land, as I like to say.

[It comes down to] the chord choices, and melodic choices. There are some intervals and licks that are commonly used — that you just kind of adopt, and it becomes a part of you.

Tell me about your accompanists on Bewitched, as well as its producers and engineers.

I work very closely with my producer, Spencer Stewart, who also did my first album; he's like my musical soulmate. We nerd out about jazz and classical music all day. But then, he's a really wonderful producer of pop music as well. So, it's this really great combination.

Basically, what I do is: I'll write the song, bring it to him, and we'll usually lay down a guitar or voice or something. We did most of the album in his home studio, and we just jumped around; I would play guitar or piano, he would play drums and bass, I would play cello.

It would just take a day or two, and we'd have a track. It was very organic, in that way — a very modern approach to recording jazzy songs. Which I hope is something that gives it that unique touch.

There's one track on the album that we recorded at EastWest Studios in Hollywood, on Frank Sinatra's piano, which was so cool. Two of the songs we recorded with the Philharmonia Orchestra, the orchestra based out of London.

There was an orchestra conductor there, and an engineer that I worked with. But for the most part, it's produced by Spencer and me.

You're doing a lot to bridge the gap to a younger generation. But what caused that gap in the first place? Historically, what has lent itself to this disconnect?

I think about this a lot. I think the barriers to entry with jazz are too high. I think young kids feel like they need to be educated to speak about it, and to even listen to it.

I think it's done such a disservice to the music that it's gotten to that point. Because in the beginning, jazz music was kind of built on freedom from rules — just expression. And it was kind of meant to be something for everybody.

I think also the nature of Gen Z — and young people at all — is that they don't want to listen to adults. They want to hear something from someone their own age. So, it's my hope that I can tie these worlds together and introduce them to something via my own 24-year-old voice.

5 Artists Who Prove That The Great American Songbook Is Brilliantly Alive

More than 50 years after its release, Simon & Garfunkel's "Bridge Over Troubled Water" lives on as one of the most respected songs in American music history. Earning the No. 66 spot on Rolling Stone's 500 Greatest Songs of All Time, it's also one of the most covered — recorded by industry greats like Elvis Presley and Aretha Franklin.

"When you're weary/ Feeling small/ When tears in your eyes/ I will dry them all/ I'm on your side," goes the iconic opening verse. "Like a bridge over troubled water/ I will lay me down."

In this episode of ReImagined, soul newcomer Acantha Lang delivers a cover of Franklin's arrangement of "Bridge Over Troubled Water," which won a GRAMMY for Best Female R&B Vocal Performance in 1972. Lang further strips down the performance with only her voice and an electric guitar.

On June 30, Lang released her debut studio album, Beautiful Dreams, via Magnolia Blue Records, led by her breakthrough single, "He Said / She Said." In an Instagram post, Lang revealed that the LP "is filled with personal stories, my life experiences, my truth."

Lang is touring through Europe, with two more stops in Paris, France, and Southend-on-Sea, United Kingdom.

Press play on the video above to hear Acantha Lang's rendition of "Bridge Over Troubled Water," and check back to GRAMMY.com for more new episodes of ReImagined.

How Gladys Knight & The Pips' "Midnight Train To Georgia" Cemented Their Legacy In Soul

Almost 30 years ago, Alanis Morissette painted heartbreak through a series of unfortunate and (debatably) "Ironic" situations, like "rain on your wedding day" or "a 'No Smoking' sign on your cigarette break." As she declared in the outro, "Life has a funny way of sneaking up on you" — because when everything is going right, something is bound to go wrong.

In this episode of ReImagined, Aliah Sheffield delivers her soulful rendition of Morissette's "Ironic." While the R&B songstress' vocal delivery remains faithful to the original recording, her classic R&B production gives it a soothing twist.

Sheffield's performance also pays homage to Morissette's music video — but rather than singing in a car during a wintery day as Morissette did 27 years earlier, Sheffield rides down a decrepit desert road in a convertible.

Outside of covers, Sheffield released her debut solo project, These Songs Are For Anyone Sick of Earth, on June 9 via Def Jam Recordings, led by singles "Earth Is Ghetto" and "Boo Boo The Fool." (The former also inspired the name of her book club, Earth Is Ghetto, I Wanna Read.)

Press play on the video above to hear Aliah Sheffield's cover of Alanis Morissette's "Ironic," and check back to GRAMMY.com for more new episodes of ReImagined.

7 Artists From R&B's New Class: Coco Jones, Kiana Ledé, Phabo & More

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

Explore More: Songbook: How Jay-Z Created The 'Blueprint' For Rap's Greatest Of All Time

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

Explore More: 5 Women Essential To Rap: Cardi B, Lil' Kim, MC Lyte, Sylvia Robinson & Tierra Whack

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.

Listen: Essential Hip-Hop Releases From The 2000s: T.I., Lil Wayne, Kid Cudi & More

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

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