As Jay-Z declared in 2001's "Breathe Easy," few rappers stack up when it comes to his flow, consistency, stories, charisma, and trendsetting powers — and he's backed up his claims for three decades on.

The Brooklyn rapper has cranked out chart-topping hits and street anthems across classic albums like The Blueprint and The Black Album, and he's inspired generations of rappers to take on his pen-free approach to music. But long before becoming a hip-hop icon, the young Shawn Carter first honed his musical gifts by rapping over a boombox in his childhood home in Bed-Stuy's Marcy Projects.

Nicknamed "Jazzy" for his love of music, Jay-Z split his time between exploring his newfound passion and dealing crack cocaine as a teenager. After linking with childhood friend and then-mentor Jaz-O, he adopted the moniker "Jay-Z" in the late 1980s, and eventually captivated hip-hop fans on the posse cut "Show and Prove" from Big Daddy Kane's 1994 album Daddy's Home. That moment led to the eventual release of his own single, 1995's "In My Lifetime," and the years that followed served as the coronation of one of rap's biggest stars.

After being rejected from major record labels, Jay linked with fellow New Yorkers Damon "Dame" Dash and Kareem "Biggs" Burke to establish Roc-A-Fella Records in 1996. He soon went from being an up-and-coming artist selling burned CDs out of his car to producing multi-platinum singles and No. 1 albums. 

His greatness has earned him 24 GRAMMYs to date — tied with Kanye West for the most of any rapper — and a spot in the Rock & Roll Hall of Fame. And with a billion-dollar business empire to match his acclaimed discography, Jay-Z has long been declared one of the greatest MCs ever. 

As he continues his rap reign, revisit some of Hov's most illustrious career moments, from memorable performances to groundbreaking album releases and legacy-defining accolades. 

Listen to GRAMMY.com's official Songbook: An Essential Guide To Jay-Z playlist on Spotify, Apple Music, Amazon Music, and Pandora. Playlist powered by GRAMMY U.

THE RISE

"Hawaiian Sophie" (1989)

A fresh-faced, hi-top faded Jay made one of his earliest appearances on wax with "Hawaiian Sophie." The 1989 record was a modest and playful hit by childhood friend Jaz-O, who let Jay contribute a few lines on the island-themed track.

Though Jay's presence was minor, he put a face to a relatively unknown name by popping up throughout the song's luau-style video. Years later, he gained the attention of legendary Brooklyn rapper Big Daddy Kane, who brought Jay on as a hype man before he broke out as a solo act and formed a more calculated, sharp-tongued lyrical style. 

Reasonable Doubt (1996)

Taking inspiration from classic films like The Godfather and Goodfellas, Jay-Z showcased his lyrical potency and storytelling ability on his critically acclaimed debut, Reasonable Doubt, in mafioso fashion. The album was the manifesto of a 26-year-old street hustler, who looked to shed the deadly perils of the drug underworld to bask in the caviar and champagne lifestyle.

He shifted from the colorful, bombastic rap style of his early career to a snappier and grounded delivery on "Coming of Age," and the Biggie Smalls-assisted "Brooklyn's Finest," while still offering a slice of mainstream appeal on "Ain't No N—" featuring Foxy Brown. Legendary producers DJ Premier ("Fried or Foe"), DJ Clark Kent ("Cashmere Thoughts"), and Ski ("Dead Presidents II") helped lay the canvas for Jay-Z to illustrate his past experiences and impending accolades and riches. 

The album was among his best releases in the '90s, and helped establish his foothold in the industry through the new millennium. While Reasonable Doubt didn't reach platinum status until six years after its 1996 release, the project elevated Jay's profile as an emerging MC with a penchant for vivid street tales and mainstream edge. 

Vol. 2... Hard Knock Life (1998)

Jay-Z's third album is possibly the most impactful in his career. Not only did it notch his first GRAMMY (for Best Rap Album at the 1999 GRAMMYs), but it remains his best-selling album with more than 5 million copies sold. It also started an 11-album streak of No. 1 releases.

The project was a medley of pop-oriented singles such as "Can I Get A…" and club records like the piano-laced hit "Money, Cash, Hoes." It also offered street classics like "Hard Knock Life (Ghetto Anthem)," which showcased his musical versatility and mainstream appeal. 

Aside from the Stevie J-produced "Ride Or Die," Jay veered away from the Bad Boy production style of Vol. 2's predecessor, In My Lifetime, Vol. 1. He enlisted Ruff Ryders producer Swizz Beatz for "Coming of Age (Da Sequel)," and producers Timbaland, Jermaine Dupri, Irv Gotti, and Kid Capri were also tapped for the project, creating a lush palette of club bangers and records indicative of the shiny-suit era of late '90s hip-hop. 

THE ANTHEMS

"Imaginary Players" (1997)

If it wasn't for Hov, rappers may still be drinking beer over champagne, rocking silver charms over platinum, and driving Range Rover 4.0 SEs instead of 4.6 HSEs. Not only did Jay shift the motor and champagne industry with his second album, but he altered the rap game, too. And "Imaginary Players" was proof.

The In My Life, Vol. 1 cut was a collective side-eye to frauds masked as street hustlers, and signaled Jay-Z's early trendsetting powers. The song didn't graze the Billboard charts as high as singles "Who You Wit," "The City Is Mine" and "(Always Be My) Sunshine," but it grew into a street anthem and blueprint for the real go-getters to shine among the fakes. 

"Big Pimpin'" (1999)

For years, "Big Pimpin'" was the ultimate summer anthem. The single from Vol 3… Life and Times of S. Carter showcased Jay's ability to produce hit records with artists from other regions. It also laid the ground for future collaborations between Jay-Z and Timbaland, who went on to produce tracks like "Dirt Off Your Shoulder," "The Bounce," "Tom Ford," and others.

Music aside, the song's video is reflective of the flashy, big-budget era of the late 1990s and early 2000s. Shot during the Trinidad and Tobago Carnival, the video's yacht views, sand-filled beaches, and cigar smoke complimented the song's tropical sound and inspired listeners to wrap themselves in linen garments, kick back and enjoy the Caribbean breeze. 

The Blueprint (2001)

Regarded as the best album in his catalog, 2001's The Blueprint encapsulated all of the elements that made Jay-Z a lyrical titan and fixture in music. Between the boundless braggadocio on "The Rules Back," the tales of chaotic romance on "Girls. Girls, Girls," and a snapshot of his uprising on "Blueprint ("Momma Loves Me"), the album captured it all.

While "The Takeover" sparked one of the era's most contentious rap beefs, and forced Queens rapper Nas to snap back with a poignant blow of his own in "Ether," the album was riddled with some of Jay's biggest records during the 2000s. Street anthems like "Izzo (H.O.V.A.)" had rap fans of all ages spelling out the song's title, and soul-stirring album cuts like "Song Cry" had listeners barely holding onto their tears. 

The Black Album (2003)

Jay's eighth studio effort was pegged as the final one by the Brooklyn MC. And while he eventually returned for Kingdom Come three years later, 2003's The Black Album would've been the perfect end to an already historic rap career.

On "December 4th," Jay kicked off the album with a call back to his origins. "They say they never really miss you 'til you dead or you gone/ So on that note I'm leaving after this song/ See you ain't got to feel no way about Jay so long/ At least let me tell you why I'm this way, hold on." 

Jay goes on to outline his successes on "What More Can I Say," then incites fans to level up their sexy on "Change Clothes." Between experimental records like the DJ Quik-produced "Justify My Thug" and the soulful "Lucifer," The Black Album is also filled with stadium-rocking anthems. 

On "99 Problems," Jay raps over zingy guitar riffs for a bold track that's reminiscent of Run DMC and Aerosmith's 1986 smash "Walk This Way." Both songs were produced by Rick Rubin, who provided the rock-induced, bare-bones beat for Hov to unleash on snarky law enforcers and uninformed rap critics. 

The Timbaland-produced "Dirt Off Your Shoulder" is a middle finger to the dream killers envious of others' success. The platinum-selling record even inspired Barack Obama to use a shoulder-brushing motion when running against then-rival Hillary Clinton during his 2008 Democratic nomination campaign. 

THE COLLABS

"Numb/Encore" (2004)

After dropping a live album with The Roots and releasing two critically panned collaborations with R. Kelly, Jay made a creative pivot with Collision Course (EP). The rapper teamed up with Linkin Park for a hip-rock project that was inspired by Danger Mouse's The Grey Album, and mashed hits like "Jigga What, Jigga Who," "Dirt Off Your Shoulder," "Big Pimpin'" and with songs from Linkin Park's Meteora and Hybrid Theory releases.

The album received mixed reviews, but the project's lone single "Numb/Encore" won Best Rap/Sung Collaboration at the 48th GRAMMY Awards and helped the EP land a No. 1 spot on the Billboard 200. 

"Empire State of Mind" (2009)

Fifteen years after Nas' "N.Y. State of Mind," Jay made his own dedication to New York City with "Empire State of Mind." The record is an ode to the city that shaped him, and the millions of other natives who, like him, hustled in various boroughs to get by (and have a closet full of New York Yankees hats).

The Alicia Keys-assisted track touched the hearts of New Yorkers everywhere, including Harlem and Brooklyn native Lil Mama, who notoriously hopped on stage with Keys and Jay during their performance at the 2009 MTV Video Music Awards. The Blueprint 3 single took home two gramophones at the 53rd GRAMMY Awards for Best Rap-Sung Collaboration and Best Rap Song. 

Watch the Throne (2011)

After teaming up on classic songs like "Never Let Me Down" and "Diamonds From Sierra Leone (Remix)," Jay and Kanye West came together for a full-length project in 2011. The two rap giants combined their musical genius for Watch the Throne, an explorative and enthralling body of work filled with genre-melding hits coated with top-tier production and memorable features.

Watch the Throne was an exercise in musical cohesion and set the bar for collab projects to follow, given the commercial success and critical reception it received upon its release. Jay served as the lyrical orator, while West was the sonic architect and more animated showman. 

Between glossy trap songs like "H.A.M." and "N—s In Paris, and the pop-extravagance of "Lift Off," Jay and Kanye tell fervent tales of their ghetto origins on "Murder To Excellence," visions of their children's lives on "New Day," and give listeners soul-stirring jams like "The Joy" and "Otis." Each track was nourished from the well of Jay and Kanye's artistry, and done without either rapper leaving the other to dry. 

"Holy Grail" (2013)

The same year Jay-Z and Justin Timberlake came together for the hit "Suit & Tie," the pair delivered another smash with "Holy Grail." The song's origins began in the sessions for Watch the Throne, but Hov feared it would get lost in the shuffle — so he decided to build 2013's Magna Carta… Holy Grail around the enthralling record.

An explosive track about the allure and destruction of fame, it became the lead single for MCHG, selling over 3 million copies and winning Best Rap/Sung Collaboration at the 2014 GRAMMYs. A year after its release, Billboard placed the record at No. 25 on the publication's Top 100 Hot Rap Songs of all-time list. 

EVERYTHING IS LOVE (2018)

Prior to 2018, Jay-Z and his wife, Beyoncé, blessed fans with culture-shifting collaborations like "Crazy in Love," "03 Bonnie and Clyde," and "Drunk in Love." These songs prompted fans to call for a full-length project from the power duo, and after years of anticipation, the power couple delivered 2018's EVERYTHING IS LOVE.

The album came as a surprise to fans, with many jarred by the rumors surrounding Jay and Beyoncé's marriage following the release of Bey's searing 2016 project Lemonade (as well as Jay's honest response with 4:44 — more on that later). While the speculations and alleged drama continue to swirl online, the two stars came together for a nine-track album that gave listeners a behind-the-scenes look at life at the Carter residence. 

Announced in the middle of their second On The Run stadium tour, EVERYTHING IS LOVE celebrated the power of black love and family life while exploring unadulterated extravagance. Like their past collaborations, Beyoncé's soothing, high-powered vocals helped elevate Jay's bars and artistry. 

Together, they combined their collective powers for stories about rowdy tour stops and endless shopping sprees on "APES—" and "BOSS," and Beyoncé adorned the album with emotion-filled love ballads like "SUMMER." The couple even exchanged braggadocious rhymes about the strength of their union on "LOVEHAPPY," and the fun they have together outside the lines of celebrity on "HEARD ABOUT US" — proving they had not only weathered the storm, but came out stronger together.

THE LEGACY

4:44 (2017)

Arguably one of Jay's most complete and honest bodies of work, 4:44 is a vivid look at the artist's triumphs and failures as Shawn Carter the man. On the opening track "Kill Jay Z," he sheds his ego-fueled moniker to reveal his early upbringing in Bed-Stuy on "Marcy Me," the discovery of his mother's sexuality on "Smile" and the issues surrounding his marriage on the title track.

While the late-career album was largely viewed as a response to Beyoncé's Lemonade album,  4:44 also painted a portrait of Black America, unveiled the pathway to generational wealth on "The Story of O.J.," and the value of shared successes on "Family Feud" and "Legacy."  

The rapper veered from the commercial sound of Blueprint 3, and the gumbo of trap and luxury-soaked beats on Magna Carta… Holy Grail, to deliver deeply personal messages over No I.D.'s grounded, sample-heavy production. 

The artist hasn't released another solo project since 4:44, but if it is in fact his last album, it's certainly a stellar way to close the door on a legendary music career. The 2017 release was praised by critics and garnered three nominations at the 60th GRAMMY Awards, including Song Of The Year and Album Of The Year. 

"GOD DID" (2022)

The GRAMMY-nominated song had plenty of star power thanks to John Legend, Lil Wayne, Rick Ross, Fridayy and producer DJ Khaled — but Jay-Z's verse tilted the hip-hop world on its axis. 

On "GOD DID," Jay spit one of the best verses in his catalog. "I be speaking to the souls of men/ Those of them willing to die for the existence that this cold world has chose for them/ Kicking snow off a frozen Timb (woo)/ Back and forth on this turnpike, really took a toll on them." The MC detailed his journey across state lines to live out his street dreams, the drama and misfortunes that followed his tracks, and how he leveraged his powers to become one of the first rappers to reach billionaire status.

He encapsulated it all within a four-minute verse, closing out the track touching on his legacy — and proclaiming that he is in fact one of rap's all-time greats. "I just got a million off a sync/ Without risking a million years tryna get it out the sink (woo)/ Hov big/ They said they don't know me internationally, n—s on the road did/ I see a lot of Hov in Giggs/ Me and Meek could never beef, I freed that n—a from a whole bid/ Hov did/ Next time we have a discussion who the GOAT, you donkeys know this."

Killer Mike Says His New Album, 'Michael,' Is "Like A Prodigal Son Coming Home"

Hip-hop would not exist without sampling. Over its 50 years of existence, rappers, producers, and DJs have taken old music and made it new again, remixing and reinterpreting the creativity of previous generations and folding it into the culture of today. 

But not everyone is flattered when a rapper samples their song. The history of hip-hop is rife with legal battles over unauthorized samples — from the genre’s early wild west days to the modern era. Some of these controversies have had lasting implications for the entire industry. 

Below, we take a look at some of the most controversial samples in hip-hop.

Sugarhill Gang – "Rapper’s Delight" (1979)

Before "Rapper’s Delight," hip-hop was predominantly a live art form. Rappers rarely recorded and preferred to perform for a live audience, improvising freestyle raps over funk and soul records spun by DJs. The use of samplers and drum machines was not yet widespread. Nevertheless, Sylvia Robinson, a singer and studio owner who wanted to take advantage of the trend. She assembled rap group the Sugarhill Gang and invited some studio musicians to record a sound-alike version of the instrumental from Chic’s "Good Times" for them to rap over. 

The song hadn’t even reached the charts yet — though it would become the first hip-hop song to breach the Billboard Top 40 — before Nile Rodgers of Chic heard an early version at a club in Manhattan. Ironically, several members of the Sugarhill Gang as well as Fab Five Freddy had joined the band onstage at a show weeks earlier to freestyle during "Good Times." Rogers didn’t take kindly to the song being knocked off, and he and Chic bassist Bernard Edwards immediately threatened legal action, with a settlement leading to them being credited as co-writers. 

The song broke hip-hop into the mainstream, but it also set the stage for many similar cases of producers asking for forgiveness rather than permission and facing the consequences. 

Afrika Bambaataa & Soulsonic Force - "Planet Rock" (1982)

Another example of "sampling without sampling," "Planet Rock" wasn’t a straight re-recording of an earlier song like "Rapper’s Delight." After witnessing the popularity of songs by Kraftwerk in New York’s nightclubs, producer Arthur Baker and DJ Afrika Bambaataa decided to fuse the German group’s electronic music with hip-hop. 

"Planet Rock" fuses the beat from "Numbers" with the melody from "Trans-Europe Express," with Bambaataa and the Soulsonic Force rapping above, but Baker recreated both with his own instruments. They never asked permission from Kraftwerk, however, and when the band reached out to Tommy Boy Records, the label decided to give them a dollar for every copy sold, raising prices to recoup the cost. 

The song birthed a genre, electro, and influenced everything from Detroit techno to Miami bass. Years later, Kraftwerk sued another musician over unauthorized sampling, a case that went all the way to Germany’s highest court in 2016. 

The "Amen" Break (recorded 1969)

When Washington, D.C.-based soul band the Winstons recorded "Amen, Brother," they couldn’t have predicted the seven-second drum break played by Gregory Coleman would go on to become one of the most iconic, oft-replicated sounds in music. 

And yet that’s exactly what happened: After being included in drum break compilations such as Ultimate Breaks and Beats designed for DJs to loop and sample, the "Amen Break" made its way into iconic hip-hop songs from N.W.A. ("Straight Outta Compton"), Mantronix ("King of the Beats,"), 2 Live Crew ("Feel Alright Y’all"), and eventually even the "Futurama" theme song. But the break really exploded in the UK, where British dance music producers, who needed faster tracks for the exploding rave movement, sped the break up. They chopped it until "Amen Brother" was barely recognizable, with other famous breaks like "Funky Drummer" and "Think" getting similar treatment. 

Jungle, and its splinter genres drum and bass, and breakcore, resulted, and the breakbeat revolution it unleashed now influences modern pop acts such as PinkPantheress and NewJeans. According to WhoSampled, "Amen, Brother" has been sampled in 6,174 songs, which may be a low estimate. 

As the saying goes, however, revolution eats its children. Gregory Coleman, the Winstons drummer who originated the break, never saw a cent of royalties from any of it. He was homeless at the time of his death in 2006, and according to Winstons bandleader Richard Lewis Spencer he had no idea the break had made such an impact. Spencer himself has run hot and cold on the break’s impact, sometimes calling its use plagiarism, but he at least was able to make some money from it: As the last living member of the Winstons, he received $37,000 from a 2015 GoFundMe campaign aimed at repaying some of the lost royalties before he died in 2020. 

Biz Markie - "Alone Again" (1991)

In the late '70s and throughout the 1980s, hip-hop flourished creatively as a result of creative sampling. Producers such as Public Enemy’s Bomb Squad created records filled with dozens of samples — a collage-like approach that would influence artists like DJ Shadow and the Avalanches. And yet in 1991, a lawsuit over an uncleared sample threatened to snuff out the entire art form. 

Biz Markie, famous for comedic songs such as "Just A Friend," had been dragged into federal court along with Warner Bros. Records for using a portion of "Alone Again (Naturally)," a nearly-forgotten pop song from the ‘70s by Gilbert O’Sullivan. The case was a disaster for Markie and for creativity in general. The court ruled that because the label had reached out to the sample copyright holders, who withheld permission to use the song, and then released it anyway, they were guilty of blatant and willful copyright infringement. 

The defense’s argument that unauthorized sampling was widespread in the music industry was rebuffed by Judge Kevin Duffy. In his ruling — which opens by quoting the biblical commandment "Thou Shalt Not Steal" — Duffy wrote that: "The defendants...would have this court believe that stealing is rampant in the music business and, for that reason, their conduct here should be excused."  

Markie was ordered to pay $250,000 in damages and referred to (but never charged by) a criminal court on grounds of theft, reeking of racist paternalism. Yet the primary upshot of the decision — that any unapproved sample constitutes copyright infringement — was even more damaging, creating a chilling effect across hip-hop that prevented artists from making full use of the practice’s creative potential. Warner Bros. took the song off Markie’s album, and the rapper famously titled his next record All Samples Cleared! 

2 Live Crew - "Pretty Woman" (1989)

Is Luther Campbell, the don dada of Miami bass maestros 2 Live Crew, smarter than the entire Warner Bros. legal team that bungled the "Alone Again" case? Judging by the fact that he managed to drag an uncleared sample case from a much more famous artist than Gilbert O’Sullivan all the way to the Supreme Court — and win — the answer is yes. 

Like Biz Markie, 2 Live Crew had asked permission to use a sample – in this case "Oh! Pretty Woman" by Roy Orbison – and was rejected. Perhaps this came as a result of their less-than-family-friendly reputation, as the group had been in and out of the headlines fighting obscenity charges over best-selling album As Nasty As They Wanna Be. Nevertheless, they released the song anyway, and when Orbison’s label eventually sued, Campbell came up with a clever defense: fair use. 

Campbell declared the 2 Live Crew song, "Pretty Woman," was a parody of Orbison’s original, and therefore the sample constituted a legal fair use. The case went all the way to the Supreme Court, which reversed an earlier appeals court ruling that said the song couldn’t have been a fair use because of its commercial nature. They also agreed with the initial federal district court ruling that said the 2 Live Crew song was not similar enough to Orbison’s to constitute wholesale infringement. 

Ironically, Campbell himself later sued 50 Cent for using "It’s Your Birthday" in his hit single "In Da Club," while 50 later sued Rick Ross for using that song’s beat on a freestyle. 

Jay-Z feat. UGK - "Big Pimpin" (2000)

Hov ended up regretting some of the sexist lyrics on this collab with Houston’s Bun B and Pimp C, but the reason he and Timbaland ended up in court over "Big Pimpin" was a contentious sample. The producer had already forked over $100,000 to sample "Khosara Khosara" by Egyptian composer Baligh Hamdi, but this wasn’t enough for Osama Ahmed Fahmy, Hamdi’s nephew. 

Citing the Egyptian legal concept of "moral rights," Fahmy claimed in a 2005 lawsuit that the song was unlicensed because Jay-Z and Timbaland had failed to ask permission from Hamdi’s heirs. The suit was left in legal limbo for years before a California judge finally let Fahmy proceed, by which point Linkin Park had also been pulled in due to a mashup of "Big Pimpin" with their single "Papercut." During his testimony four years later, Jay-Z declared he had been unaware that there was even a sample in the song, saying "Timbaland presented me with a track. I didn’t even think about there being a sample." 

The case was finally settled in 2018 when an appeals court upheld the original summary judgment in favor of Jay-Z, by which point the song was nearly 20 years old. 

Kanye West - "Blood On The Leaves" (2013)

Quite a few of the samples used on Yeezus, Kanye’s incendiary, famously-rushed 2013 album, ended up being unauthorized. West fielded lawsuits from Hungarian prog rock band Omega (sampled on "New Slaves") and the Ponderosa Twins Plus One (sampled on "Bound 2") for using their music without permission. But it was "Blood on the Leaves" which attracted the most attention for its brazen (and fully authorized) appropriation of Nina Simone’s cover of "Strange Fruit," originally made famous by Billie Holiday. 

That a famous anti-lynching anthem was used by a mega-famous rapper to decry the materialism and excess rife within hip-hop might have ruffled a few feathers — some conservative critics even argued it was an anti-abortion song — but the song received almost universal praise. 

Robin Thicke ft. T.I. and Pharrell - "Blurred Lines" (2013)

True, "Blurred Lines" is not exactly a hip-hop track, but it does feature two rappers, and while not exactly a sample, Robin Thicke and Pharrell’s much-too-liberal "borrowing" of Marvin Gaye’s "Got to Give it Up" changed the music industry irreparably. Certainly, the song was hugely controversial, opening up a pre-#MeToo discourse over its objectification of women and glorification of rape culture that ultimately led to bans. But it was the similarities to Gaye’s song, flaunted by Willams and Thicke in the press, as well as a preemptive legal action against the Marvin Gaye estate, that had a more lasting, damaging impact. 

Williams had argued in his initial complaint against the Gaye family that their claim was not based on specific musical elements, but on the face value similarity of the two songs. However, a jury ruled unanimously in favor of the family. The case essentially rewrote the legal precedents of musical copyright law overnight, broadening the scope by which a song might be considered infringement. Thanks to the "Blurred Lines" suit, a musician may live in fear of legal predation simply because their new song sounds vaguely similar to one from 30 or 40 years ago. 

Meanwhile, massive investments are being made into older music, partially to make up for this creative chilling effect.

Juice WRLD - "Lucid Dreams" (2017)

There’s nothing particularly incendiary about the plaintive guitar sample from Sting’s "Shape of My Heart" that forms the backbone of Juice WRLD’s emo rap hit. When producer Nick Mira revealed that Sting had taken 85 percent of the rights for the song, however, it became a demonstration of how sampling has become a way for established artists to exploit newer talent. 

It also attracted a lawsuit from pop-punk band Yellowcard, who cited similarities to their track "Holly Wood Died." Juice WRLD himself downplayed the situation, saying "There’s always more money to be made." The suit was later dropped after the 21-year-old rapper’s tragic early death in December 2019. 

Young Nudy feat. Playboi Carti - "Pissy Pamper" (aka "Kid Cudi") (2019)

One of the most successful unreleased songs in recent memory is also a cautionary tale for keeping leaks under control. The song originally entitled "Pissy Pamper" was a Pi’erre Bourne-produced track originally meant for Sli’merre, his collaborative mixtape with Young Nudy. 

With its prominent use of a loop from "Tasogare" by Japanese singer Mai Yamane (best known to anime fans for "Cowboy Bebop" ending theme), the track regretfully never made the record due to sample clearance issue. But somehow, a leaked file made its way onto Spotify, where its killer component, an evocative "baby voice" verse from Playboi Carti at the peak of pre-Whole Lotta Red hysteria. 

The rest is history: internet memes, reuploads with Nudy’s parts removed, and so on. Thanks to social media, the song is a generational touchstone that shouldn’t legally exist. 

Listen To GRAMMY.com's 50th Anniversary Of Hip-Hop Playlist: 50 Songs That Show The Genre's Evolution

New York is indisputably the birthplace of hip-hop, but which of the city's five boroughs has dominated the genre continues to be a spirited debate among its scholars and natives. 

The "Boogie Down" Bronx is the origin point of hip-hop history. It’s here Clive Campbell a.k.a. DJ Kool Herc threw a rec room party in 1973 that put hip-hop as we know it in motion. The city's northernmost borough is the home of groundbreaking artists from OGs Grandmaster Flash and Slick Rick, to contemporary stars including Cardi B.

The case for Queens — home of Def Jam Records and a host of GRAMMY-winning and nominated rappers from  Run-D.M.C. and Salt-N-Pepa, to LL Cool J and Nicki Minaj — is often made. 

On her 2005 track "Lighters Up" Lil' Kim declares Brooklyn "Home of the Greatest Rappers." It’s hard to argue. Marcy Projects alone would give us Christopher Wallace a.k.a. Biggie Smalls and Jay-Z.

Manhattan also plays a role in hip-hop’s evolution as a playground where rappers intermingled with punks, rockers and the thriving art scene throughout the ‘70s and ‘80s. Elements of each of these developing artforms culminating in the music of the Beastie Boys. And because he is so often referred to as a West Coast rapper, it’s easy to forget Tupac Shakur was born in Manhattan.

Staten Island is, of course, home to the one and only Wu-Tang Clan and its diverse cosmology. Even the suburbs can boast major contributions — Long Island is the home of Public Enemy and Erik B & Rakim; head north of the Bronx to Westchester County, and you'll enter the home of the late rapper DMX.  

What’s clear when we look at each borough, is that the culture and art of hip-hop would not exist  if not for New York. Without the contributions,style and unique cultures of neighborhoods within Brooklyn, Queens, Manhattan and Staten, the artform would not have developed into the juggernaut it is today.  Press play on the Amazon Music playlist below — or visit Spotify, Pandora and Apple Music — to take an auditory tour of the best of the boroughs.

To celebrate the 50th anniversary of hip-hop, hop on the train and travel from borough to borough for its unique history and sounds.

As you examine the breadth of NYC hip-hop, you’ll find artists with a deep and complex relationship with the city. Biz Markie, for example, was born in one area of the city, raised in another, and claimed membership to a crew for a whole other borough. His story, and that of others who deserve many flowers, demonstrate that while hip-hop can be dissected by region and subway line, it’s the Big Apple's density, multiculturalism, an urban innovation that has made it arguably one of America's greatest art forms. 

Mass immigration from Puerto Rico and the Dominican Republic in the 1950s made the Bronx the first majority Black and Latino borough in NYC by the mid-'70s. It’s not a coincidence that the Bronx was also woefully unserved by the city government, resulting in bleak economic conditions.

"Kids with little or no resources created something out of nothing," the Funky Four Plus One’s MC Sha Rock told ABC News said of hip-hop's origins. "No matter what was going on around us in New York City at the time, we looked forward to the park jams." 

These jams featured breakdancing, DJs mixing, and MCing — all key elements of hip-hop that emerged from house parties and underground venues into a city-wide consciousness. "Hip-hop wasn't called hip-hop in the ‘70s, was called 'going to the jams,'" Sha Rock continued. 

A few years before the park jams took off, DJ Kool Herc’s August 1973 rec room party put hip-hop as we know it on the map. Herc took classic records and popular hits, broke down the beats, and invited MCs to chime in over them invoking the Jamaican style of delivery, talking or chanting, usually in a monotone melody, over a rhythm known as "toasting" in reggae.

In 1975, the Bronx Boys Rocking Crew (or TBB) fostered another element of hip-hop when they organized late night tagging sessions. These young graffiti artists brought the color and life of their borough to the rest of the city, as painted subway trains provided moving canvases and controversy. 

By the time the park jams were happening, some graffiti crews had expanded into competitive dance. With moves drawn from martial arts, gymnastics, and modern dance, "breaking, popping, and locking" would see b-boys and b-girls become as important as music to hip-hop as an art form. Breaking as an art has continued to flourish and will soon be an Olympic sport.

Bronx-born artists such as the Funky Four Plus One, Grandmaster Flash, Afrika Bambaataa, Melle Mel and Kurtis Blow became pioneers of the genre in the 1970s, and helped define hip-hop in the '80s. 

The borough would go on to boast Kool Keith, KRS One, Big Pun, Fat Joe, and Cardi B, among many others, as acts who have innovated the Bronx’s place in hip-hop culture. The borough is now home to the Universal Hip-Hop Museum and will host events at Sedgwick and a 50 Years of Hip-Hop concert at Yankee Stadium.

In 1990, Brooklyn was New York’s Blackest neighborhood, with 73.1 percent of its Black residents native born. The previous decade had seen Brooklyn rappers rise to prominence in hip-hop, by the end of the 1990s the world’s ear was tuned into Brooklyn.  

Known for his use of three turntables, Cutmaster DC's early tracks "Brooklyn's in the House" and "Brooklyn Rocks the Best" were the first to mention Brooklyn as a force in hip-hop music. These early '80s tracks also featured DC's pioneering technique of cutting breaks over Roland TR-909 beats, a marked moment for hip-hop's technical advancement.

Combining speed, style and humor, few would influence hip-hop's syncopation and cadence like Big Daddy Kane. In their 2012 list of The Greatest Hip-Hop Songs of All Time Rolling Stone called Kane "a master wordsmith of rap's late-golden age and a huge influence on a generation of MCs." Within a few years Brooklyn flow would be redefined by the slow deliberative annunciation of the Notorious B.I.G., whose delivery would become one of the most interpolated in rap history. 

The styles of both would be emulated and refined by a young Brooklyn rapper named Shawn Carter. The artist later known as Jay-Z attended George Westinghouse High School in downtown Brooklyn, where his classmates included Busta Rhymes, Biggie and DMX — all of whom would play a critical part in the evolution of rap’s delivery styles. 

The borough wasn’t only a boys club. MC Lyte, Foxy Brown, and new rappers like Young MA continue to put Brooklyn on the musical map.

On Aug. 11, 2023, Brooklyn locals (and GRAMMY winners) Digable Planets will headline Celebrate Brooklyn! festival's 50th anniversary of hip-hop event. 

The largest Borough by area, Queens boasts the Guiness World Record for most languages spoken and gained the nickname "The World’s Borough" for its diverse population. Whereas Bronx hip-hop was derived from Black American and Caribbean cultures, Queen’s hip-hop samples the world. While the 1970s saw the Bronx give birth to hip-hop, the 1980s saw the eastern borough of Queens mature the art form.

Queen’s hip-hop history has roots in two specific areas: the Queenborough Projects and Hollis. The Queensboro Projects, a.k.a. "The Bridge," were one of the few unsegregated projects in New York. It was also home to Marley Marl, who accidentally discovered sampling while working on a Captain Rock record as a studio intern in the early ‘80s. 

"I was actually trying to get a riff off of a record. I made a mistake and got the snare in there before the sound came," he recounted to NPR. "The snare sounded better than the snare that I had from the drum machine when I was popping it…I was like, "Hold up!" This will enable me to take any kick and a snare from any record that people love and make my own beat." Marls’ use of the 808 pulse to trigger different samplers was revolutionary, and he would become a pioneer for his ability to blend sampled and 808 drum sounds. 

Marl’s contribution would extend beyond the technical. As a member of the Juice Crew, he brought the voice of 14-year-old Roxanne Shanté to the world. She created a new lane for women in rap as well as the blueprint for the diss track on the seminal "Roxanne's Revenge." 

About a half hour east on the F Train in Hollis, Queens, brothers Joseph and Russel Simmons (a DJ and promoter respectively) founded Run-D.M.C. with friends Darryl Mc Daniels and Jason Mizell. Run-D.M.C.'s sound featured a synchronized, aggressive delivery over simple but memorable rock hooks and beats. Later, the group established Def Jam Records, the label that would prove rap could sell millions of records to Top 40 audiences and bring rap to the mainstream as the first rappers to be featured on MTV.

As valuable as the musical contributions of Run-D.M.C are, they are equally vital to the development of fashion as an element of hip-hop. Street style, as it would come to be known, is born in Queens: Kangol hats, unlaced Addias, Carzal frames, and thick gold chains are now as synonymous with hip-hop as beats and samples. Today, fashion is so central to hip-hop, and vice versa, that New York's FIT Museum recently held an expansive exhibit on hip-hop style.” 

Complex proclaimed Nas’ Illmatic "set off a seismic shift in rap geopolitics" and added that the 1994 record "galvanized Queensbridge hip-hop and by extension East Coast rap as a whole." His introspective and poetic approach to writing is credited for bringing the best out of his contemporaries and inspiring next generation rappers like Killer Mike and Kendrick Lamar, challenging them to meet his lyrical bar.

Though "The Fly Borough" is the most densely populated, the majority of its hip-hop history is concentrated in the northern Manhattan neighborhood of Harlem. 

Home of the legendary Apollo Theater, the neighborhood was well rooted in Black music when World War II vet Bobby Robinson opened Bobby’s Records in 1946 — one of Harlems’ few Black owned businesses at the time. The record store would evolve as would Robinson’s involvement in music. He would become a producer and label head whose 1970 imprint Enjoy Records released music by hip-hop's earliest innovators, including Grandmaster Flash, the Treacherous Three, and Doug E. Fresh. The label would also feature Master Don, whose signature use of a "Funk Box" percussion synthesizer and its crispy digital hi hat is still heard in trap music today.  

Harlem was also home to Dapper Dan, the first designer to "borrow" designer goods and modify them with hip-hop flair. His boutique operated from 1982-1992 and was essential to the merging of luxury brands and hip-hop culture. Although brands like Gucci first sued for copyright infringement, they eventually saw the value of hip-hop's branding power on high end fashion sales. In 2018, Dapper Dan and Gucci collaborated on a capsule collection.

Also during this ‘80s culture boom, three high schoolers from Manhattan applied the ethos of punk rock to the emerging street sounds of hip-hop. 

The Beastie Boys began by pirating rap, self-admittingly "Rhyming and Stealing" for their 1986 Def Jam debut License to Ill, and went on to forge a new lane for the medium. They broke  all the rules of sampling and production with their seminal Paul’s Boutique, which Rolling Stone noted is often dubbed "The Sargent Pepper of hip-hop" and lauded for its layer sampling technique. In their ranking of Paul’s Boutique Consequence of Sound wrote, "Paul’s Boutique sat at a finish line waiting for the rest of the world to catch up." 

While the outer Boroughs would enjoy most of the attention musically throughout the '90s and 2000s, the 2010s would see Harlem again centered in hip-hop with the arrival of young rappers like Azealia Banks and the ASAP Mob collective. 

RZA, GZA, Method Man, Raekwon, Ghostface Killah, Inspectah Deck, U-God, Masta Killa, and Ol’ Dirty Bastard and later Cappadonna would find success as both a group and  as solo artists. infiltrating the "big six" 1990s major record labels by design. You can also hear the influence of RZA on modern acts like El Michels Affair, which draws inspiration from Wu-Tang's melodic take on instrumentation and released two albums of instrumental soul covers of Wu-Tang Clan songs.

Their impact would go far beyond music however. Hip-hop biographer Will Ashon recounted Wu’s influence on fashion, noting that the group were part of a trend of simplification.

"Their whole modus operandi was to present themselves as real and unmanufactured, so their clothing choices had to reflect this. The rawness and directness of the music was supposed to be echoed in the rawness and directness of their clothing. They were a big part of the early 1990s move towards baggy and oversized clothes. Huge combat trousers or sweatpants, Timberland boots, hoodies, puffas, do-rags, gold fronts and so on. A ‘street soldier’ look." 

As you’d expect, Wu’s presence looms large over future  Staten Island artists, including G4 Boys and Killarmy. New artists like Cleotrapa, a spicy, no-holds-barred femme rapper, also counts Wu-Tang as an influence and is helping define Staten’s next chapter.

The history of the intersection of New York City and hip-hop culture is as big and diverse as the city itself. We could only touch on a handful of artists and creators in this piece, but the topic has been explored at length in books like Cant Stop Wont Stop by Jeff Chang and The Come Up: An Oral History of the Rise of Hip-Hop. Documentaries on hip-hop can be found on almost all streaming platforms Netflix’s notable Hip-Hop Evolution and Ladies First: The Story of Women in Hip-Hop. 

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It's been a turbulent five-year journey for Travis Scott bridging the worlds of ASTROWORLD to UTOPIA.

Since the 2018 GRAMMY-nominated album solidified Scott as part of rap's A-list, he's endured the highest of highs and the lowest of lows. Amid working on the album (which he began teasing in 2020), his 2021 iteration of Astroworld Festival resulted in a crowd crush that killed 10. 

Three months later, he welcomed his second child with Kylie Jenner. Earlier this year, the pair reportedly split; just weeks before UTOPIA's arrival, Scott was cleared of any criminal liability for the Astroworld Festival incident, but civil lawsuits remain to be sorted.  

Expectations were already sky-high for Scott to maintain luminary status with his ASTROWORLD follow-up. But after he experienced tragedy and heartbreak alongside triumphs and joy, Scott had all eyes on him as UTOPIA arrived on July 28. Yet, the pressure didn't seem to faze the Houston-born rapper — UTOPIA creates another euphoric world for his loyal fans.

In honor of La Flame's star-studded fourth studio LP — which is loaded with 18 features across 19 tracks — here are five early takeaways surrounding UTOPIA. 

CIRCUS MAXIMUS Is UTOPIA's Visual Companion

Fans didn't know what to expect with Scott's CIRCUS MAXIMUS, which hit select theaters mere hours prior to UTOPIA. The 76-minute film — which takes its name from a UTOPIA track — serves as more of a series of music videos centered around a conversation between the rapper and producer Rick Rubin.

"You've come a long way — is the house half empty or completely empty? How are the kids? I heard there was a tragedy," Rubin asks Scott at one point, but he takes the conversation in a different direction.

The Harmony Korine-directed movie features about half of the songs from UTOPIA and includes appearances from Sheck Wes, Yung Lean and James Blake. Scott goes from DJing a colorful dance party for "MODERN JAM" to smashing chairs and nearly burning down an ancient Italian racing stadium while "FE!N" rings off.

CIRCUS MAXIMUS also allows Scott to share his rather unexpected interpretation of what UTOPIA means inside his world. "UTOPIA is not all pretty," he says in the film. "It's how you balance the idea of confrontation."

Yeezus Rises Again

Scott and Kanye West have had a longstanding musical partnership, as Scott played an integral role behind-the-scenes of West's rebellious 2013 album, Yeezus. A decade later, West's fingerprints are all over UTOPIA — even without a vocal guest appearance.

West earned production credits on "MODERN JAM," "THANK GOD," "TELEKINESIS" and "GOD'S COUNTRY." The latter two were originally on the track list for 2021's Donda before Ye passed them off to Scott to bring across the finish line. 

Elsewhere, "CIRCUS MAXIMUS" is essentially a "Black Skinhead" part two; it interpolates the rugged Yeezus standout, and it was co-produced by Noah Goldstein, Ye's audio engineer for most of his career. 

Trav's most blunt pledge to Kanye came on "Skitzo," which calls back to West's alleged presidential bid for 2024. "I'm loyal, b—, I got Ye over Biden," Scott candidly raps.

Drake And Travis Scott Take Aim At Their Opps Once Again

Drake and Travis Scott have proven to be a winning combination in the past with diamond-certified smashes like "SICKO MODE," and they aimed to recreate that magic with "MELTDOWN."

Right out of the gate, Drake makes a fiery statement with bars seemingly addressing Pusha T — but he's really sniping his close friend Pharrell, mirroring his shots at Kanye West in his "SICKO MODE" verse.

"I melt down the chains that I bought from yo' boss," Drake raps in reference to a Skateboard P pendant he recently purchased at an auction from Pharrell. The 6 God goes on to diss Pharrell's new position as a creative director at Louis Vuitton and claims nobody's messing with the designer brand since the 2021 death of former head Virgil Abloh.

"Give a f— about all of that heritage s—/ Since V not around, the members done hung up the Louis/ They not even wearing that s—," he continues.

Scott joined Drake in the sinister "tensions rising" theme, subliminally dissing Wonka star Timothée Chalamet, who has reportedly been dating his ex Kylie Jenner. "Chocolate AP and chocolate the Vs (Vs), got the Willy Wonka factory/Burn a athlete like it's calories, find another flame hot as me, b—," Scott spits.

While "Meltdown" may not reach the same commercial heights as "SICKO MODE," it has certainly caused a stir on social media. "Drake went crazy… I love when dude starts gettin' chippy!" Hot 97's Ebro Darden wrote on Twitter. As another fan claimed, "Rap been boring. I gotta thank Drake honestly for wanting to get back in the ring."

Scott Finally Got His Dream Collab

Perhaps one of UTOPIA's buzziest cameos comes from Beyoncé, who appears on "DELRESTO (ECHOES)." It marks a full-circle moment for Scott, too, as he has long tried to manifest a collab with his fellow Houston native, publicly declaring his hopes for a Bey team-up to Complex in 2016. (Prior to UTOPIA's release, eagle-eyed fans noticed that the newspaper cover art for "DELRESTO (ECHOES)" had been incorporated as part of Bey's Renaissance Tour decor.)

As Bey continues to ride out her RENAISSANCE groove, Scott fits in well with his hypnotic flow. And in a rather surprising twist, Bon Iver's Justin Vernon rounds out the track by pouring in his ethereal vocals behind the triumphant Hit-Boy production.

While Bey does much of the heavy lifting on "DELRESTO (ECHOES)," Scott's verse still stands out as he declares he won't give up on a new love interest. "The starry nights, they start to fade (Come on)/ At times, for miles I see your face, yeah," Scott testifies, borrowing from Kanye's "Coldest Winter" flow.

"MODERN JAM" Is The Hit Fans Will Eventually Catch On To

Scott's Ragers normally rush to collide for a sweaty moshpit when his music comes on. But with the genre-bending UTOPIA track "MODERN JAM," La Flame's moving the crowd from the mosh pit to the dance floor.

According to Kanye West fan page Donda's Place, "MODERN JAM" is a 10-year-old alternate version of the raw beat that became Yeezus' "I Am A God." Travis expertly meshes the abrasiveness of Ye's hard-hitting 808s with a groovy baseline. And with production help from Daft Punk's Guy-Manuel de Homem-Christo, the Teezo Touchdown-assisted track is a good bet to slow-burn its way to major chart success — even if it has a different feel than what Scott's fans are used to.

Since the beginning of Scott's career, he has been a trendsetter pushing the boundaries of what's considered mainstream hip-hop. He knows how to introduce foreign sonics in such a digestible way that it allows him to take creative risks and still thrive as a commercial titan — and UTOPIA is proof that he hasn't lost his Midas touch.

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

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

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

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

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

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

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

Snoop Dogg- Doggystyle (1993)

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

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

A Tribe Called Quest - Midnight Marauders (1993)

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

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

Digable Planets - Blowout Comb (1994)

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

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

2Pac - Me Against the World (1995)

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

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

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

Jay-Z - Reasonable Doubt (1996)

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

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

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

Lil’ Kim - Hard Core (1996)

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

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

Missy Elliott - Supa Dupa Fly (1997)

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

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

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

Outkast - Aquemini (1998)

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

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

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

Dr. Dre - 2001 (1999)

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

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

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