meta-scriptOutKast Examine Their Southern Experience On 'Southernplayalisticadillacmuzik' | GRAMMY.com

OutKast in 1994

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OutKast Examine Their Southern Experience On 'Southernplayalisticadillacmuzik'

When fledgling duo "Big Boi" Patton and André "André 3000" Benjamin released their first album in the midst of the '90s East Coast-West Coast hip-hop rivalry, nothing else in the world sounded quite like it

GRAMMYs/May 8, 2019 - 11:25 pm

Long before they amassed six GRAMMY awards, sold millions of records, and toured to sold-out crowds around the world, the duo of Antwon "Big Boi" Patton and André "André 3000" Benjamin were just a couple of teenagers in Atlanta, sharing their experience through freestyling. And when they released their first album as OutKast in the midst of the East Coast-West Coast hip-hop rivalry, nothing else in the world sounded quite like it. It's been 25 years since the 1994 release of Southernplayalisticadillacmuzik, and there's still nothing like it. "Big Boi and I were just fans of the music of the time and enjoyed rhyming," Benjamin tells the Recording Academy over the phone. "I'm from the South. I lived it, saw it, and just spit it back out."

Benjamin and Patton met at a shopping mall as 16 year olds, which quickly led to rapping in the cafeteria at school. Not long after, they and schoolmates Goodie Mob caught the attention of hometown production trio Sleepy Brown, Rico Wade, and Ray Murray, collectively known as Organized Noize, and the whole group came together in a fluid collaborative troupe eventually known as the Dungeon Family. "When we were working on the OutKast vibe, even though there were two members in the group, we all considered ourselves OutKast at the time—including all of Organized Noize and the Goodie Mob members who appeared on the album," Murray says over the phone.

Benjamin remembers being immediately entranced by Organized Noize's style. "Rico Wade brought us to his house studio, where I heard the most interesting music production I'd ever heard from Atlanta," he says. "It was Rico, Ray, and Sleepy's vision to make sure [OutKast would put] Southern lifestyle first. I was just playing my part the best I could."

Despite that modesty, it's clear from the earliest OutKast recordings that Patton and Benjamin had an irrepressible charisma. While still in high school, the duo signed with LaFace Records, the Arista imprint run by L.A. Reid and Babyface. Before their first record, OutKast made waves with an appearance on a remix of fellow LaFace artists TLC’s "What About Your Friends" and the magnetic single "Player’s Ball," which was released as a Christmas single.

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"It was the first rap act we signed to LaFace, and it was my idea to release a Christmas single. Nothing about that was supposed to work, but it was the beginning of what turned out to be one of the most incredible careers," Reid tells the Recording Academy. Reid had been focused largely on pop and R&B, and propelled his career into one of the most prominent producers and record executives across decades—eventually turning Epic records into a hip-hop hub. After leaving Epic in 2017 (Editor's note: Reid's transition out of Epic is tied to allegations of sexual harrassment), Reid has since formed his own organization, HitCo Entertainment, where Big Boi is currently signed. "All I knew was that I loved Big Boi, I loved André, and I loved Organized Noize, and the record sounded incredible," Reid says. "I've since learned every lyric to every one of their songs, and can rap along word for word. They became my favorite artists that I’ve ever worked with."

That captivating sound comes in large part from the ways in which Organized Noize and the rest of the Family took inspiration from music spanning much farther and deeper than the monolithic "East" and "West" hip-hop sounds presented to mass audiences at face value. Per Murray, the production draws inspiration from New York to Oakland, from pop appeal to intense musicality. "There were two ends of the spectrum—Jermaine [Dupri] was a hometown guy, and he discovered Kris Kross, and that was a major thing. And then on the other side of the coin, you had [Dr. Dre's] The Chronic, which laid down the blueprint of craftsmanship and symmetry," Murray says. "Kris Kross were as big as you could be; they went around the world being from Atlanta without being [in] Atlanta. And then The Chronic was about being as impactful as possible. Somewhere in between, you've got New York sh*t, Hit Squad, Redman, and Das EFX, and then all the way out to Oakland. You have all of these different kinds of ways to maintain your integrity, which is the culture of hip-hop, but you can then still try to express it in terms of your neighborhood. As we put all that stuff together and stirred it up, that's what clicked for us.”

Those elements came to the surface in Southernplayalisticadillacmuzik, an album that reached number 20 on the Billboard 200 and garnered rave reviews, but also left some confused. OutKast weren’t afraid of leaning into local slang and had no interest in catering to the expectations of radio rap. In fact, it seems they weren’t even considering that reality. "We had our own lifestyle and lingo and confidence from the inside, so it really didn’t matter what everyone else thought," Benjamin says. "I didn't really think it was so left field at the time. I just thought it sounded good and because we were all in The Dungeon making it, as a whole. People would stop by The Dungeon, or later on by the studio, and it was like a listening party damn near every night. People smoked, partied, and conversed to what we were making—so that was the proof to us. The Atlanta pride was there, because we believed it."

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While he would end up producing tracks for OutKast beginning with 1998's Aquemini, Benjamin started writing while listening to other music rather than creating himself. "I actually wrote a lot of the verses that ended up on the first album to R&B songs. like Janet Jackson's 'Let’s Wait a While' and 'Funny How Time Flies,' Loose Ends' 'You Can’t Stop the Rain,' and Tony Toni Toné’s 'Anniversary,'" he says. "I always felt more deeply, wrote more deeply with chords involved. They color the mood. Bass-lines, too. The beat was just the time keeper for me."

For Murray, the Atlanta-ness of the record extended always to a place of civic pride and activism. "Atlanta is the home of Dr. Martin Luther King and Andrew Young, as well as the first black mayor, Maynard Jackson. We were rooted in mobility and progressiveness as black people in America," he says. "And that translated into not wanting to identify with New York or L.A., but to personify Atlanta and its thought process. It's a great confluence of what we believe in, what we were raised in, and we wanted to show that to the world."

From a production standpoint, Organized Noize first cut their teeth professionally on Parental Advisory's Ghetto Street Funk, released on Pebbles' Savvy Records imprint. Though they'd been developing their musical influences prior to that record, Ghetto Street Funk taught them much more about communicating with their fanbase. "On the Parental Advisory record, we were trying to talk to people we didn't know. But for Southernplayalisticadillacmuzik, we decided to talk to everybody we know," Murray says. "We tried using New York terminology, trying to reach them with a dialogue we didn't have. But it's amazing that the culture of Atlanta is a barometer for what's really going on. If it works in Atlanta, it works in Detroit, it works in Chicago, it works wherever you have urban centers."

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By focusing on what they knew, Organized Noize and OutKast found the world coming to them, rather than needing to push for attention. The record sold half a million copies in the first few months, and was certified platinum within a year. Critics lauded the fusion of p-funk influences, live instrumentation, and bold coming-of-age tales of life in the modern South. Organized Noize's writing and production were injected with the electric personality of André 3000 and Big Boi, while the young rappers found a frenetic footing for their burgeoning talents. "I can't explain the gravity, attraction, or soundscape of that record. We were merely hired young guns that only rapped on the record, which [Organized Noize] produced in its entirety," Benjamin says.

Beyond the traditional critical acclaim, the record had people within the entertainment world buzzing as well. Legendary director John Singleton had been a big enough fan of Southernplayalisticadillacmuzik that he reached out to Organized Noize when he began production on Higher Learning. "John Singleton said that a lot of the movie was based on Big Rube's interludes on this album," Murray says. "In essence, Ice Cube is playing Big Rube off of Southernplayalistic in that movie."

Now, 25 years later, the record has only grown more beloved, garnered more of a following and inspired more growing artists and enlivened more lives. But for the men involved in the record's creation, listening back to Southernplayalisticadillacmuzik is more of a complex proposition. "I actually cringe now when listening to it because I hear how I was still trying to find who I was as a young man with many influences—good and bad," Benjamin says. "I was only about three years away from living a pretty strict life with just my mom and I, so I was essentially still a momma's boy that got sent to live with my dad and that's when I met Big Boi. Then we met Rico, Ray, Sleepy, Gipp and what would later become The Dungeon Family."

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Murray, meanwhile, listens to the record from time to time as a reminder of the fire of that moment. "We just had the competitive spirit of young lions looking at old lions,: he laughs. "I have all faith in God, I put it all on the record, and faith is rewarded because people are saved by it. We’re still talking about Southernplayalisticadillacmuzik 25 years later."

But, perhaps most important, both in propelling their growth as artists and a tight-knit group that would go on to produce more mind-blowing records, Benjamin looks back to the debut as a family affair, an experience of discovering a whole new life. "Rico, Ray, Sleepy, Gipp, and what would later become The Dungeon Family—I watched and learned from them like big brothers. I'm an only child so this was great for me," he says. "Another world opened up for me then and it came fast. The characters I met, the experiences, the odd trying to fit in, trying to belong to something is all heard on that record. I cringe to my rhyming because I could barely even pronounce my words clearly. And I can hear all of my influences. As time went on, I heard more and more confidence in myself and that inspired more freedom to explore. I've found some creative freedom and have developed a little more in areas. I’m always concerned with the discovery or newness of things, which keeps me invested. Otherwise, I'm dead."

On 'Things Fall Apart,' The Roots Deepened Hip-Hop

Notorious B.I.G. Biggie Smalls in 1994
Notorious B.I.G. in Brooklyn, 1994

Photo: Clarence Davis/NY Daily News Archive via Getty Images

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How 1994 Changed The Game For Hip-Hop

With debuts from major artists including Biggie and Outkast, to the apex of boom bap, the dominance of multi-producer albums, and the arrival of the South as an epicenter of hip-hop, 1994 was one of the most important years in the culture's history.

GRAMMYs/Feb 13, 2024 - 05:22 pm

While significant attention was devoted to the celebration of hip-hop in 2023 — an acknowledgement of what is widely acknowledged as its 50th anniversary — another important anniversary in hip-hop is happening this year as well. Specifically, it’s been 30 years since 1994, when a new generation entered the music industry and set the genre on a course that in many ways continues until today.

There are many ways to look at 1994: lists of great albums (here’s a top 50 to get you started); a look back at what fans and tastemakers were actually listening to at the time; the best overlooked obscurities. But the best way to really understand why a single 365 three decades ago had such an impact is to narrow our focus to look at the important debut albums released that year. 

An artist’s or group’s debut is their entry into the wider musical conversation, their first full statement about who they are and where in the landscape they see themselves. The debuts released in 1994 — which include the Notorious B.I.G.'s Ready to Die, Nas' Illmatic and Southernplayalisticadillacmuzik from Outkast — were notable not only in their own right, but because of the insight they give us into wider trends in rap.

Read on for some of the ways that 1994's debut records demonstrated what was happening in rap at the time, and showed us the way forward. 

Hip-Hop Became More Than Just An East & West Coast Thing

The debut albums that moved rap music in 1994 were geographically varied, which was important for a music scene that was still, from a national perspective, largely tied to the media centers at the coasts. Yes, there were New York artists (Biggie and Nas most notably, as well as O.C., Jeru the Damaja, the Beatnuts, and Keith Murray). The West Coast G-funk domination, which began in late 1992 with Dr. Dre’s The Chronic, continued with Dre’s step brother Warren G

But the huge number of important debuts from other places around the country in 1994 showed that rap music had developed mature scenes in multiple cities — scenes that fans from around the country were starting to pay significant attention to.

To begin with, there was Houston. The Geto Boys were arguably the first artists from the city to gain national attention (and controversy) several years prior. By 1994, the city’s scene had expanded enough to allow a variety of notable debuts, of wildly different styles, to make their way into the marketplace.

Read more: A Guide To Texas Hip-Hop: Definitive Releases, Artists & Events

The Rap-A-Lot label that first brought the Geto Boys to the world’s attention branched out with Big Mike’s Somethin’ Serious and the Odd Squad’s Fadanuf Fa Erybody!! Both had bluesy, soulful sounds that were quickly becoming the label’s trademark — in no small part due to their main producers, N.O. Joe and Mike Dean. In addition, an entirely separate style centered around the slowed-down mixes of DJ Screw began to expand outside of the South Side with the debut release by Screwed Up Click member E.S.G.

There were also notable debut albums by artists and groups from Cleveland (Bone Thugs-N-Harmony, Creepin on ah Come Up), Oakland (Saafir and Casual), and of course Atlanta — more about that last one later.

1994 Saw The Pinnacle Of Boom-Bap

Popularized by KRS-One’s 1993 album Return of the Boom Bap, the term "boom bap" started as an onomatopoeic way of referring to the sound of a standard rap drum pattern — the "boom" of a kick drum on the downbeat, followed by the "bap" of a snare on the backbeat. 

The style that would grow to be associated with that name (though it was not much-used at the time) was at its apex in 1994. A handful of primarily East Coast producers and groups were beginning a new sonic conversation, using innovations like filtered bass lines while competing to see who could flip the now standard sample sources in ever-more creative ways. 

Most of the producers at the height of this style — DJ Premier, Buckwild, RZA, Large Professor, Pete Rock and the Beatnuts, to name a few — worked on notable debuts that year. Premier produced all of Jeru the Damaja’s The Sun Rises in the East. Buckwild helmed nearly the entirety of O.C.’s debut Word…Life. RZA was responsible for Method Man’s Tical. The Beatnuts took care of their own full-length Street Level. Easy Mo Bee and Premier both played a part in Biggie’s Ready to Die. And then there was Illmatic, which featured a veritable who’s who of production elites: Premier, L.E.S., Large Professor, Pete Rock, and Q-Tip.

The work the producers did on these records was some of the best of their respective careers. Even now, putting on tracks like O.C.’s "Time’s Up" (Buckwild), Jeru’s "Come Clean" (Premier), Meth’s "Bring the Pain" (RZA), Biggie’s "The What" (Easy Mo Bee), or Nas’ "The World Is Yours" (Pete Rock) will get heads nodding.

Major Releases Balanced Street Sounds & Commercial Appeal

"Rap is not pop/If you call it that, then stop," spit Q-Tip on 1991’s "Check the Rhime." Two years later, De La Soul were adamant that "It might blow up, but it won’t go pop." In 1994, the division between rap and pop — under attack at least since Biz Markie made something for the radio back in the ‘80s — began to collapse entirely thanks to the team of the Notorious B.I.G. and his label head and producer Sean "Puffy" Combs. 

Biggie was the hardcore rhymer who wanted to impress his peers while spitting about "Party & Bulls—." Puff was the businessman who wanted his artist to sell millions and be on the radio. The result of their yin-and-yang was Ready to Die, an album that perfectly balanced these ambitions. 

This template — hardcore songs like "Machine Gun Funk" for the die-hards, sing-a-longs like "Juicy" for the newly curious — is one that Big’s good friend Jay-Z would employ while climbing to his current iconic status. 

Solo Stars Broke Out Of Crews

One major thing that happened in 1994 is that new artists were created not out of whole cloth, but out of existing rap crews. Warren G exploded into stardom with his debut Regulate… G Funk Era. He came out of the Death Row Records axis — he was Dre’s stepbrother, and had been in a group with a pre-fame Snoop Dogg. Across the country, Method Man sprang out of the Wu-Tang collective and within a year had his own hit single with "I’ll Be There For You/You’re All I Need To Get By." 

Anyone who listened to the Odd Squad’s album could tell that there was a group member bound for solo success: Devin the Dude. Keith Murray popped out of the Def Squad. Casual came out of the Bay Area’s Hieroglyphics. 

Read more: A Guide To Bay Area Hip-Hop: Definitive Releases, Artists & Subgenres From Northern California

This would be the model for years to come: Create a group of artists and attempt, one by one, to break them out as stars. You could see it in Roc-a-fella, Ruff Ryders, and countless other crews towards the end of the ‘90s and the beginning of the new millennium.

Multi-Producer Albums Began To Dominate

Illmatic was not the first rap album to feature multiple prominent producers. However, it quickly became the most influential. The album’s near-universal critical acclaim — it earned a perfect five-mic score in The Source — meant that its strategy of gathering all of the top production talent together for one album would quickly become the standard. 

Within less than a decade, the production credits on major rap albums would begin to look nearly identical: names like the Neptunes, Timbaland, Premier, Kanye West, and the Trackmasters would pop up on album after album. By the time Jay-Z said he’d get you "bling like the Neptunes sound," it became de rigueur to have a Neptunes beat on your album, and to fill out the rest of the tracklist with other big names (and perhaps a few lesser-known ones to save money).

The South Got Something To Say

If there’s one city that can safely be said to be the center of rap music for the past decade or so, it’s Atlanta. While the ATL has had rappers of note since Shy-D and Raheem the Dream, it was a group that debuted in 1994 that really set the stage for the city’s takeover.

Outkast’s Southernplayalisticadillacmuzik was the work of two young, ambitious teenagers, along with the production collective Organized Noize. The group’s first video was directed by none other than Puffy. Biggie fell so in love with the city that he toyed with moving there

Outkast's debut album won Best New Artist and Best New Rap of the Year at the 1995 Source Awards, though the duo of André 3000 and Big Boi walked on stage to accept their award to a chorus of boos. The disrespect only pushed André to affirm the South's place on the rap map, famously telling the audience, "The South got something to say." 

Read more: A Guide To Southern Hip-Hop: Definitive Releases, Artists & Subgenres From The Dirty South

Outkast’s success meant that they kept on making innovative albums for several more years, as did other members of their Dungeon Family crew. This brought energy and attention to the city, as did the success of Jermain Dupri’s So So Def label. Then came the "snap" movement of the 2000s, and of course trap music, which had its roots in aughts-era Atlanta artists like T.I. and producers like Shawty Redd and DJ Toomp. 

But in the 2010s a new artist would make Atlanta explode, and he traced his lineage straight back to the Dungeon. Future is the first cousin of Organized Noize member Rico Wade, and was part of the so-called "second generation" of the Dungeon Family back when he went by "Meathead." His world-beating success over the past decade-plus has been a cornerstone in Atlanta’s rise to the top of the rap world. Young Thug, who has cited Future as an influence, has sparked a veritable ecosystem of sound-alikes and proteges, some of whom have themselves gone on to be major artists. 

Atlanta’s reign at the top of the rap world, some theorize, may finally be coming to an end, at least in part because of police pressure. But the city has had a decade-plus run as the de facto capital of rap, and that’s thanks in no small part to Outkast. 

Why 1998 Was Hip-Hop's Most Mature Year: From The Rise Of The Underground To Artist Masterworks

Performers onstage during "A GRAMMY Salute To 50 Years Of Hip-Hop"
Performers onstage during "A GRAMMY Salute To 50 Years Of Hip-Hop"

Photo: Frazer Harrison/Getty Images for The Recording Academy

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6 Highlights From "A GRAMMY Salute To 50 Years Of Hip-Hop": Performances From DJ Jazzy Jeff & The Fresh Prince, Queen Latifah, Common & More

A multi-generational collective of artists commemorated the culture, sound and influence of hip-hop during a two-hour televised special. Read on for the biggest moments from "A GRAMMY Salute To 50 Years Of Hip-Hop," which aired Dec. 10.

GRAMMYs/Dec 11, 2023 - 07:50 pm

While 2023 marked hip-hop's 50th anniversary, the year comes to a close with a show that proves the celebration can't, and won't stop. On Dec. 10, the Recording Academy's "A GRAMMY Salute To 50 Years Of Hip-Hop" paid homage to the culture's originators, innovators, and contemporary leaders.

Co-produced by Questlove, the two-hour televised special featured legendary acts and contemporary artists who have cultivated the genre into a pop cultural juggernaut. Icons including LL Cool J, DJ Jazzy Jeff & The Fresh Prince, Jermaine Dupri, Too Short, E-40, De La Soul, DJ D-Nice, Doug E. Fresh and others transformed "A GRAMMY Salute To 50 Years Of Hip-Hop" into an oral and visual commemoration of hip-hop's enduring influence.

From regional tributes to poetic remembrances, the anniversary special was a showcase of adoration for hip-hop's OGs as well as a newer generation of entertainers who are leading hip-hop into a glorious next 50 years

Read on for six highlights from  "A GRAMMY Salute To 50 Years Of Hip-Hop," which aired Sunday, Dec. 10 on CBS Television Network, and on demand on Paramount+.

Queen Latifah and Monie Love┃Frazer Harrison/Getty Images for The Recording Academy

Ladies First: Honoring The Queens Of Hip-Hop

The audience erupted into thunderous applause the moment DJ Spinderella touched the ones and twos and Queen Latifah graced the stage. As the two went back and forth in a performance of "Ladies First" joined by British MC Monie Love, the tone was set: This was a celebration of and for the women in hip-hop. 

As the song closed, early pioneers MC Sha-Rock and Roxanne Shante joined the trio on stage to perform their signature hits. In a continued showcase of women’s evolution in hip-hop, J.J. Fad performed their early crossover hit "Supersonic," while MC Lyte, Remy Ma, and Latto also joined onstage. As a collective, the congregation closed out with a performance of "U.N.I.T.Y." 

DJ Paul and Juicy J of Three 6 Mafia┃Frazer Harrison/Getty Images for The Recording Academy

The South Still Got Something To Say

One could not imagine the impact of André 3000's words at the Source Awards in 1995 when he said "the South got something to say." Since then, rappers from Atlanta, Baton Rouge, Memphis, Miami, and Texas have taken these words as a rallying cry that the East and West coasts aren't the only regions worthy of hip-hop’s crowns. 

Aptly described as "The Third Coast," the South was well-represented onstage. Jeezy and Jermaine Dupri showcased the universal power of Atlanta, while Bun B represented the great state of Texas and the legacy of Pimp C in his performance of "International Players Anthem." Memphis took it back with a performance of "Stay Fly" by Three 6 Mafia, while viewers were reminded of the city’s future by an enthusiastic presentation of "Tomorrow" by GloRilla

Boosie Badazz stole the stage with his rendition of "Wipe Me Down," which highlighted the cities outside of the Atlanta, Houston, and Memphis corridor which contributed to the development and prominence of Southern hip-hop. His energy was enlightened by Miami Luke, the man behind 2 Live Crew, who brought booty shaking Miami bass to stage to round out the intergenerational collective of performers from down South. 

Explore More Of "A GRAMMY Salute to 50 Years of Hip-Hop"

(L-R) Yukmouth and Kuzzo Fly of The Luniz, Yo-Yo, The Lady of Rage, B-Real and Sen Dog of Cypress Hill┃Monica Schipper/Getty Images for The Recording Academy

…But The West Coast Remains The Best Coast

The West Coast was among the first to differentiate itself from the East Coast with the invention of G-funk — a musical tradition that blended resurrected funk samples with live instrumentation to create a melodic background for the region’s musicians to rap upon. One of the first hits to crossover was "Regulate" by Warren G, which opened the special’s tribute to the West Coast. 

The song was followed by chart topping "I Got 5 on It" by Luniz, a cult classic which received a secondary wave of prominence by Jordan Peele who remixed the song for his film Us. However, it was the performances by The Lady of Rage and Yo-Yo that served as an educational lesson for those who forget about the contributions of women to the growth of the West Coast sound in hip-hop. 

Another standout from the West Coast section was Cypress Hill, the Southern California hip-hop group that blended rock, metal, and Latin music in hip-hop. Yet, it was the presence of E-40 and Too Short that solidified the importance of the Bay Area in the lineage of West Coast hip-hop.

Flavor Flav of Public Enemy, T.I., and Chuck D of Public Enemy┃Monica Schipper/Getty Images for The Recording Academy

"Salute" Paid Tribute To Those Who Didn’t Make It To 50

Jay-Z turned 54 days before "A GRAMMY Salute To 50 Years Of Hip-Hop" aired, and it was  somber to consider his contemporaries who didn't make it to see the culture's golden anniversary.

Names such as the Notorious B.I.G., who grew up with Jay-Z, as well as Nipsey Hussle were shared on screen as DJ D-Nice and Doug E. Fresh paid respect to the legions of rappers who passed before hip-hop’s 50th. Among those honored were Tupac Shakur, his friend and frontman of Digital Underground Shock G, New York drill leader Pop Smoke, TakeOff of the Migos, and Gangsta Boo — all of whom were instrumental in making hip-hop the global force that it is today.

Rick Ross, Chance the Rapper and 2 Chainz┃Frazer Harrison/Getty Images for The Recording Academy

Hip-Hop Got A Big "Happy Birthday"

Hip-hop and party culture have been interwoven since DJ Kool Herc and Cindy Campbell threw the first party at 1520 Sedgwick Avenue in the Bronx. It's only fitting that the genre’s 50th anniversary would be ushered in with "Birthday Song" by 2 Chainz. As the Atlanta rapper reminded attendees that the best place to celebrate your birthday is in the city's strip clubs, Gunna graced the stage with his verse of "Hot" from Young Thug’s album So Much Fun.

It was the sample of Grandmaster Flash and The Furious Five’s "The Message" that brought hip-hop’s back home to the East Coast with a riveting performance by Coi Leray. Although, Rick Ross, Nelly, and Chance The Rapper reminded the East of the party and chart potential of Miami St. Louis, and Chicago with their rendition of "Hustlin," "E.I.," and "No Problem."

DJ Jazzy Jeff and Will Smith a.k.a. the Fresh Prince┃Frazer Harrison/Getty Images for The Recording Academy

DJ Jazzy Jeff & The Fresh Prince Got Thanks And Praise

It was the advocacy of DJ Jazzy Jeff & The Fresh Prince that encouraged bridge-building between the Recording Academy and the hip-hop community. When the duo received hip-hop’s first GRAMMY Award for Best Rap Performance, the rapper/producer elected to boycott the show. Although they attended the following year, the duo displayed a courageous appreciation of their art that continues to be appreciated by their peers. 

Questlove introduced his fellow Philadelphians and the duo erupted into a medley of their classics. Soon, LL Cool J, Queen Latifah, and others jumped up to pay homage to Jeff and Will, two children from Philadelphia who changed the world.

2023 In Review: 5 Trends That Defined Hip-Hop

LL Cool J

Credit: Paul Natkin/Getty Images

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20 Iconic Hip-Hop Style Moments: From Run-D.M.C. To Runways

From Dapper Dan's iconic '80s creations to Kendrick Lamar's 2023 runway performance, hip-hop's influence and impact on style and fashion is undeniable. In honor of hip-hop's 50th anniversary, look back at the culture's enduring effect on fashion.

GRAMMYs/Nov 29, 2023 - 03:01 pm

In the world of hip-hop, fashion is more than just clothing. It's a powerful means of self-expression, a cultural statement, and a reflection of the ever-evolving nature of the culture.

Since its origin in 1973, hip-hop has been synonymous with style —  but the epochal music category known for breakbeats and lyrical flex also elevated, impacted, and revolutionized global fashion in a way no other genre ever has.   

Real hip-hop heads know this. Before Cardi B was gracing the Met Gala in Mugler and award show red carpets in custom Schiaparelli, Dapper Dan was disassembling garment bags in his Harlem studio in the 1980s, tailoring legendary looks for rappers that would appear on famous album cover art. Crescendo moments like Kendrick Lamar’s performance at the Louis Vuitton Men’s Spring-Summer 2023 runway show in Paris in June 2022 didn’t happen without a storied trajectory toward the runway.

Big fashion moments in hip-hop have always captured the camera flash, but finding space to tell the bigger story of hip-hop’s connection and influence on fashion has not been without struggle. Journalist and author Sowmya Krishnamurphy said plenty of publishers passed on her anthology on the subject, Fashion Killa: How Hip-Hop Revolutionized High Fashion, and "the idea of hip hop fashion warranting 80,000 words." 

"They didn't think it was big enough or culturally important," Krishnamurphy tells GRAMMY.com, "and of course, when I tell people that usually, the reaction is they're shocked."

Yet, at the 50 year anniversary, sands continue to shift swiftly. Last year exhibitions like the Fashion Institute of Technology’s Fresh, Fly, and Fabulous: Fifty Years of Hip-Hop Style popped up alongside notable publishing releases including journalist Vikki Tobak’s, Ice Cold. A Hip-Hop Jewelry Story. Tabak’s second published release covering hip-hop’s influence on style, following her 2018 title, Contact High: A Visual History of Hip-Hop.

"I wanted to go deeper into the history," Krishnamurphy continues. "The psychology, the sociology, all of these important factors that played a role in the rise of hip-hop and the rise of hip-hop fashion"

What do the next 50 years look like? "I would love to see a hip-hop brand, whether it be from an artist, a designer, creative director, somebody from the hip-hop space, become that next great American heritage brand," said Krishnamurphy.

In order to look forward we have to look back. In celebration of hip-hop’s 50 year legacy, GRAMMY.com examines iconic moments that have defined and inspired generations. From Tupac walking the runways at Versace to Gucci's inception-esque knockoff of Dapper Dan, these moments in hip-hop fashion showcase how artists have used clothing, jewelry, accessories, and personal style to shape the culture and leave an indelible mark on the world.

*The cover art to Eric B and Rakim’s* Paid in Full

Dapper Dan And Logomania: Luxury + High Fashion Streetwear

Dapper Dan, the legendary designer known as "the king of knock-offs," played a pivotal role in transforming luxury fashion into a symbol of empowerment and resistance for hip-hop stars, hustlers, and athletes starting in the 1980s. His Harlem boutique, famously open 24 hours a day, became a hub where high fashion collided with the grit of the streets.

Dapper Dan's customized, tailored outfits, crafted from deconstructed and transformed luxury items, often came with significantly higher price tags compared to ready-to-wear luxury fashion. A friend and favorite of artists like LL Cool J and Notorious B.I.G., Dapper Dan created iconic one-of-a-kind looks seen on artists like Eric B and Rakim’s on the cover of their Paid in Full album.

This fusion, marked by custom pieces emblazoned with designer logos, continues to influence hip-hop high fashion streetwear. His story — which began with endless raids by luxury houses like Fendi, who claimed copyright infringement — would come full circle with brands like Gucci later paying homage to his legacy.

Athleisure Takes Over

Hip-hop's intersection with sportswear gave rise to the "athleisure" trend in the 1980s and '90s, making tracksuits, sweatshirts, and sneakers everyday attire. This transformation was propelled by iconic figures such as Run-D.M.C. and their association with Adidas, as seen in photoshoots and music videos for tracks like "My Adidas."

*LL Cool J. Photo: Paul Natkin/Getty Images*

LL Cool J’s Kangol Hat

The Kangol hat holds a prominent place in hip-hop fashion, often associated with the genre's early days in the '80s and '90s. This popular headwear became a symbol of casual coolness, popularized by hip-hop pioneers like LL Cool J and Run-D.M.C. The simple, round shape and the Kangaroo logo on the front became instantly recognizable, making the Kangol an essential accessory that was synonymous with a laid-back, streetwise style.

*Dr. Dre, comedian T.K. Kirkland, Eazy-E, and Too Short in 1989. Photo: Raymond Boyd/Getty Images*

N.W.A & Sports Team Representation

Hip-hop, and notably N.W.A., played a significant role in popularizing sports team representation in fashion. The Los Angeles Raiders' gear became synonymous with West Coast hip-hop thanks to its association with the group's members Dr. Dre, Eazy-E, and Ice Cube, as well as MC Ren.

 *Slick Rick in 1991. Photo: Al Pereira/Getty Images/Michael Ochs Archives*

Slick Rick’s Rings & Gold Chains

Slick Rick "The Ruler" has made a lasting impact on hip-hop jewelry and fashion with his kingly display of jewelry and wealth. His trendsetting signature look — a fistful of gold rings and a neck heavily layered with an array of opulent chains — exuded a sense of grandeur and self-confidence. Slick Rick's bold and flamboyant approach to jewelry and fashion remains a defining element of hip-hop's sartorial history, well documented in Tobak's Ice Cold.

Tupac Walks The Versace Runway Show

Tupac Shakur's runway appearance at the 1996 Versace runway show was a remarkable and unexpected moment in fashion history. The show was part of Milan Fashion Week, and Versace was known for pushing boundaries and embracing popular culture in their designs. In Fashion Killa, Krishnamurpy documents Shakur's introduction to Gianni Versace and his participation in the 1996 Milan runway show, where he walked arm-in-arm with Kadida Jones.

*TLC. Photo: Tim Roney/Getty Images*

Women Embrace Oversized Styles

Oversized styles during the 1990s were not limited to menswear; many women in hip-hop during this time adopted a "tomboy" aesthetic. This trend was exemplified by artists like Aaliyah’s predilection for crop tops paired with oversized pants and outerwear (and iconic outfits like her well-remembered Tommy Hilfiger look.)

Many other female artists donned oversized, menswear-inspired looks, including TLC and their known love for matching outfits featuring baggy overalls, denim, and peeking boxer shorts and Missy Elliott's famous "trash bag" suit worn in her 1997 music video for "The Rain." Speaking to Elle Magazine two decades after the original video release Elliot told the magazine that it was a powerful symbol that helped mask her shyness, "I loved the idea of feeling like a hip hop Michelin woman."

Diddy Launches Sean John

Sean "Diddy" Combs’ launch of Sean John in 1998 was about more than just clothing. Following the success of other successful sportswear brands by music industry legends like Russell Simmons’ Phat Farm, Sean John further represented a lifestyle and a cultural movement. Inspired by his own fashion sensibilities, Diddy wanted to create elevated clothing that reflected the style and swagger of hip-hop. From tailored suits to sportswear, the brand was known for its bold designs and signature logo, and shared space with other successful brands like Jay-Z’s Rocawear and model Kimora Lee Simmons' brand Baby Phat.

 *Lil' Kim. Photo: Ron Galella/Ron Galella Collection via Getty Images*

Lil’ Kim Steals The Show

Lil' Kim’s daring and iconic styles found a kindred home at Versace with

In 1999, Lil' Kim made waves at the MTV Video Music Awards with her unforgettable appearance in a lavender jumpsuit designed by Donatella Versace. This iconic moment solidified her close relationship with the fashion designer, and their collaboration played a pivotal role in reshaping the landscape of hip-hop fashion, pushing boundaries and embracing bold, daring styles predating other newsworthy moments like J.Lo’s 2000 appearance in "The Dress" at the GRAMMY Awards.

Lil Wayne Popularizes "Bling Bling"

Juvenile & Lil Wayne's "Bling Bling" marked a culturally significant moment. Coined in the late 1990s by Cash Money Records, the term "bling bling" became synonymous with the excessive and flashy display of luxury jewelry. Lil Wayne and the wider Cash Money roster celebrated this opulent aesthetic, solidifying the link between hip-hop music and lavish jewelry. As a result, "bling" became a cornerstone of hip-hop's visual identity.

Jay-Z x Nike Air Force 1

In 2004, Jay-Z's partnership with Nike produced the iconic "Roc-A-Fella" Air Force 1 sneakers, a significant collaboration that helped bridge the worlds of hip-hop and sneaker culture. These limited-edition kicks in white and blue colorways featured the Roc-A-Fella Records logo on the heel and were highly coveted by fans. The collaboration exemplified how hip-hop artists could have a profound impact on sneaker culture and streetwear by putting a unique spin on classic designs. Hova's design lives on in limitless references to fresh white Nike kicks.

Daft Punk and Pharrell Williams. Photo: Mark Davis/WireImage

Pharrell Williams' Hat At The 2014 GRAMMYs

Pharrell Williams made a memorable red carpet appearance at the 2014 GRAMMY Awards in a distinctive and oversized brown hat. Designed by Vivienne Westwood, the hat quickly became the talk of the event and social media. A perfect blend of sartorial daring, Pharrell's hat complemented his red Adidas track jacket while accentuating his unique sense of style. An instant fashion moment, the look sparked innumerable memes and, likely, a renewed interest in headwear.

Kanye’s Rise & Fall At Adidas (2013-2022)

Much more than a "moment," the rise and eventual fall of Kanye’s relationship with Adidas, was as documented in a recent investigation by the New York Times. The story begins in 2013 when West and the German sportswear brand agreed to enter a partnership. The collaboration would sell billions of dollars worth of shoes, known as "Yeezys," until West’s anti-semitic, misogynistic, fat-phobic, and other problematic public comments forced the Adidas brand to break from the partnership amid public outrage.

Supreme Drops x Hip-Hop Greats

Supreme, with its limited drops, bold designs, and collaborations with artists like Nas and Wu-Tang Clan, stands as a modern embodiment of hip-hop's influence on streetwear. The brand's ability to create hype, long lines outside its stores, and exclusive artist partnerships underscores the enduring synergy between hip-hop and street fashion.

*A model walks the runway at the Gucci Cruise 2018 show. Photo: Pietro D'Aprano/Getty Images*

Gucci Pays "homage" to Dapper Dan

When Gucci released a collection in 2017 that seemingly copied Dapper Dan's distinctive style, (particularly one look that seemed to be a direct re-make of a jacket he had created for Olympian Dionne Dixon in the '80s), it triggered outrage and accusations of cultural theft. This incident sparked a conversation about the fashion industry's tendency to co-opt urban and streetwear styles without proper recognition, while also displaying flagrant symbols of racism through designs.

Eventually, spurred by public outrage, the controversy led to a collaboration between Gucci and Dapper Dan, a significant moment in luxury fashion's acknowledgement and celebration of the contributions of Black culture, including streetwear and hip-hop to high fashion. "Had Twitter not spotted the, "Diane Dixon" [jacket] walking down the Gucci runway and then amplified that conversation on social media... I don't think we would have had this incredible comeback," Sowmya Krishnamurphy says.

A$AP Rocky x DIOR

Self-proclaimed "Fashion Killa" A$AP Rocky is a true fashion aficionado. In 2016, the sartorially obsessed musician and rapper became one of the faces of Dior Homme’s fall/winter campaign shot by photographer Willy Vanderperre — an early example of Rocky's many high fashion collaborations with the luxury European brand.

A$AP Rocky's tailored style and impeccable taste for high fashion labels was eloquently enumerated in the track "Fashion Killa" from his 2013 debut album Long. Live. ASAP, which namedrops some 36 luxury fashion brands. The music video for "Fashion Killa" was co-directed by Virgil Abloh featuring a Supreme jersey-clad Fenty founder, Rihanna long before the two became one of music’s most powerful couples. The track became an anthem for hip-hop’s appreciation for high fashion (and serves as the title for Krishnamurphy’s recently published anthology). 

*Cardi B. Photo: Steve Granitz/WireImage*

Cardi B Wears Vintage Mugler At The 2019 GRAMMYs

Cardi B has solidified her "it girl" fashion status in 2018 and 2019 with bold and captivating style choices and designer collaborations that consistently turn heads. Her 2019 GRAMMYs red carpet appearance in exaggerated vintage Mugler gown, and many custom couture Met Gala looks by designers including Jeremy Scott and Thom Browne that showcased her penchant for drama and extravagance.

But Cardi B's fashion influence extends beyond her penchant for custom high-end designer pieces (like her 2021 gold-masked Schiaparelli look, one of nine looks in an evening.) Her unique ability to blend couture glamour with urban chic (she's known for championing emerging designers and streetwear brands) fosters a sense of inclusivity and diversity, and makes her a true trendsetter.

Beyoncé & Jay-Z in Tiffany & Co.’s "About Love" campaign

The power duo graced Tiffany & Co.'s "About Love'' campaign in 2021, showcasing the iconic "Tiffany Yellow Diamond," a 128.54-carat yellow worn by Beyoncé alongside a tuxedo-clad Jay-Z. The campaign sparked controversy in several ways, with some viewers unable to reconcile the use of such a prominent and historically significant diamond, sourced at the hands of slavery, in a campaign that could be seen as commercializing and diluting the diamond's cultural and historical importance. Despite mixed reaction to the campaign, their stunning appearance celebrated love, adorned with Tiffany jewels and reinforced their status as a power couple in both music and fashion.

Kendrick Lamar Performs At Louis Vuitton

When Kendrick Lamar performed live at the Louis Vuitton Men’s spring-summer 2023 runway show in Paris in June 2022 following the passing of Louis Vuitton’s beloved creative director Virgil Abloh, he underscored the inextricable connection between music, fashion and Black American culture.


Lamar sat front row next to Naomi Campbell, adorned with a jeweled crown of thorns made from diamonds and white gold worth over $2 million, while he performed tracks including "Savior," "N95," and "Rich Spirit'' from his last album, Mr. Morale and the Big Steppers before ending with a repeated mantra, "Long live Virgil." A giant children’s toy racetrack erected in the Cour Carrée of the Louvre became a yellow brick road where models marched, clad in designer looks with bold, streetwear-inspired design details, some strapped with oversized wearable stereo systems.

Pharrell Succeeds Virgil Abloh At Louis Vuitton

Pharrell Williams' appointment as the creative director at Louis Vuitton for their men's wear division in 2023 emphasized hip-hop's enduring influence on global fashion. Pharrell succeeded Virgil Abloh, who was the first Black American to hold the position.

Pharrell's path to this prestigious role, marked by his 2004 and 2008 collaborations with Louis Vuitton, as well as the founding of his streetwear label Billionaire Boy’s Club in 2006 alongside Nigo, the founder of BAPE and Kenzo's current artistic director, highlights the growing diversity and acknowledgment of Black talent within high fashion.

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

André 3000 and Big Boi of Outkast in October 1998
André 3000 and Big Boi of Outkast in October 1998

Photo: Raymond Boyd/Getty Images

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Why 1998 Was Hip-Hop's Most Mature Year: From The Rise Of The Underground To Artist Masterworks

From the release of 'The Miseducation of Lauryn Hill' and 'Aquemini,' to the proliferation of underground rap and the rise of regionalism, 1998 was hip-hop's sweet spot.

GRAMMYs/Nov 20, 2023 - 03:02 pm

2023 has seen countless tributes to hip-hop, celebrating both its golden anniversary and the staying power of a genre that was vilified, underestimated, and branded a passing fad for decades. Nonetheless, while 50 is a major milestone, many believe hip-hop reached its peak decades ago.  

At the tail end of the golden age of hip-hop, the genre reached a new level of maturity. Twenty-five years ago, hip-hop music demonstrated a wide variety of production styles and a diversity of perspectives. Further proving that 1998 was a high watermark for hip-hop, several important and stylistically distinct albums by Jay-Z, Black Star, A Tribe Called Quest and Outkast were even released on the same day.

This diversity of expression resulted in multiple commercially successful, distinct subgenres and niche audiences. The culture moved beyond the bi-coastal hostility that had culminated in the tragic murders of Tupac and Biggie, and the South asserted itself in a big way. The year’s versatility was demonstrated through the emergence of an underground scene that was critical of mainstream hip-hop’s consumerist mentality, but nonetheless thrived alongside commercially successful albums by both new and established artists.  

Southern Hip-Hop Earns Respect 

By 1998 groups beyond the East and West Coasts had started to gain national visibility — a hallmark of hip-hop's growing maturity. 

While Outkast's Andre 3000 famously declared that  "The South got somethin’ to say" in1995, the group didn't earn widespread respect and recognition until three years later. Released in September 1998, Aquemini, garnered near-universal praise — earning Outkast a notoriously rare five mics in The Source — and is still considered to be one of hip-hop’s greatest albums. 

No other hip-hop group sounded like Outkast, and Southern flavor and slang pervaded the album (see the harmonica breakdown in "Rosa Parks"), but it was also the live instrumentation on tracks like "Liberation" and "SpottieOttieDopaliscious" that made the album so special. 

Fellow ATLiens Goodie MOB, a group in the Dungeon Family collective, also released an album in '98. Like Aquemini, their sophomore effort Still Standing was produced largely by Organized Noize and featured a similar production style. 

Outkast and Goodie MOB collaborated often in the 1990s: Aquemini’s "Liberation" only works because of the deeply soulful vocals of Goodie MOB’s Cee-Lo, and Still Standing’s "Black Ice" features one of Andre 3000’s most poetic and brilliant verses. While speaking to the many struggles of being young, Black and poor in the South, these two groups demonstrated how regional pride could be asserted in a more positive way, instead of spilling over into real-life violence; it was evidence of hip-hop’s maturity.

On the more commercial side, Atlanta rapper/producer Jermaine Dupri — who was already producing and writing songs for major R&B artists like Usher and Mariah Carey — released his debut album, resulting in one of the hits of the summer: the bouncy Jay-Z collaboration "Money Ain’t A Thang." New Orleans was also becoming an important locus of Southern hip-hop by 1998, with Master P’s No Limit Records releasing albums by Master P himself, Silkk the Shocker, C-Murder, Mystikal, and Snoop Dogg. Hits included "Make ‘Em Say Ugh" and "It Ain’t My Fault," both containing Mystikal’s distinctive high-pitched growling; his lightning-fast verse on the first song is truly something to behold. Also from Crescent City, Cash Money Records struck gold with Juvenile’s 400 Degreez and his booty-shaking anthem, "Back That Azz Up."

The Rise of Underground Hip-Hop

1998 was also the year "underground" hip-hop bubbled to the surface as a reaction to the genre’s crossover success. It was defined primarily by a critique of the presumed excessive consumerism of mainstream hip-hop, and a desire to return to the days when DJs, b-boys and graffiti artists were as important as rappers. 

Turntablism was strongly associated with this style, as were cyphers — gatherings where rappers, b-boys and beatboxers would form a circle and engage in freestyle battles. The emergence of underground hip-hop was another sign that the genre was maturing as a whole; artists were no longer as worried about the ghettoization by the music industry and some felt that it had strayed too far from its marginalized roots. 

The most significant underground hip-hop album of 1998 was Mos Def and Talib Kweli are Black Star, created by a young duo of Brooklyn MCs. Interestingly, it was released on the same day in September as Aquemini, as well as two other major albums of the year: Jay-Z’s Vol. 2…Hard Knock Life and A Tribe Called Quest’s The Love Movement — which although not an essential listen in their discography, did produce a hit with "Find A Way." Four major albums released on the same day was a testament to how far hip-hop had come. 

In fact, the Black Star album was an explicit critique of the type of consumerist mentality and sexually explicit/boasting lyrics Jay-Z employed on Hard Knock Life. Songs like "Definition" display Mos Def and Talib Kweli’s exceptional lyrical dexterity and clever references, while  "Hater Players" draws a clear line in the sand between commercial hip-hop and the "real MCs." In the latter, Kweli raps: "We ain't havin’ that, reachin’ past the star status that you grabbin’ at/ My battle raps blast your ass back to your natural habitat."

Mos Def’s adaptation of Slick Rick’s "Children’s Story" is a clever screed about the lack of originality within mainstream hip-hop. "They jacked the beats, money came wit' ease, but son, he couldn't stop, it's like he had a disease. He jacked another and another, Michael Jackson, Stevie Wonder." The song was a not-so-veiled reference to the production technique utilized by Puff Daddy, relying heavily on well-known samples of soul and R&B songs.

Black Star also distinguished itself from much of commercial rap of the time by uplifting, instead of denigrating, women. "Brown Skin Lady" is an ode to Black women throughout the African diaspora, presenting a clear contrast to the frequent use of the b-word on Hard Knock Life, particularly on one of its biggest hits, "Can I Get A…" Nonetheless, like many "conscious" rappers — notably, Common, who makes a guest appearance on this album — Black Star reflects the almost-universal homophobia in hip-hop at the time, particularly in Mos Def’s verse on "Re-Definition." 

Despite Jay-Z’s distrust and demonization of women on Hard Knock Life — his third and most commercially successful record — no one can dispute his tremendous verbal prowess and flow, evident on tracks like "N— What, N— Who." And while he called out "gold diggers" in "Can I Get A…," he invited a female rapper (Amil) onto the song — leveling the playing field a bit. 

Production-wise, Jay-Z’s use of the "Annie" theme for the title song was one of the most inspired choices in the genre’s history. The slick production of the album guaranteed it would be a home run; in retrospect, it heralded the future of commercial hip-hop’s sound.  

Oher underground hip-hop artists were making big waves in 1998. Rawkus Records — which released the Black Star album — put out an important compilation, Lyricist Lounge, Volume 1, which featured performances by Mos Def, Talib Kweli, A Tribe Called Quest’s Q-Tip, and the L.A.-based Jurassic 5, who also released their debut album that year. Other West Coast underground artists who released debut albums in 1998 included the Bay Area-based Hieroglyphics and Rasco, and the L.A.-based Aceyalone and People Under the Stairs. 

Debuts, Veterans And The Biggest Album Of The Year 

1998 also saw the release of important debut albums by commercial hip-hop artists like DMX, Big Pun and Black Eyed Peas. Big Pun’s "Still Not A Player" was one of the biggest hits of the year, with his lyricism reminiscent of Biggie

DMX had a particularly productive year, releasing two albums in 1998, It’s Dark and Hell Is Hot and Flesh of My Flesh, Blood of My Blood. That year, it was impossible to escape the melodic hook and chorus of "Ruff Ryders’ Anthem" ("Stop! Drop! Shut ‘em down, open up shop") from the first DMX album. DMX also contributed a memorable verse on the Lox’s hit "Money, Power, Respect," off the group’s debut album, released by Puffy’s Bad Boy. 

Beyond the debut albums of 1998, a slew of established artists from various regions and representing myriad styles put out their third, fourth or fifth albums. East Coast artists with new albums included Beastie Boys, Method Man, Redman, Busta Rhymes, Queen Latifah, Gang Starr, Mc Lyte, and Public Enemy, who released a soundtrack album for Spike Lee’s He Got Game. On the West Coast, there were new albums by Cypress Hill, Ice Cube, and Digital Underground. 

Notwithstanding the success of so many diverse hip-hop artists, no album achieved greater heights than Lauryn Hill’s masterful solo debut, The Miseducation of Lauryn Hill. To start, it won Album Of The Year at the 1999 GRAMMYs, a feat never before accomplished for a hip-hop artist, as well as four other golden gramophones. Hill wrote, arranged and produced the album herself, reportedly turning down offers for production help from both her former Fugees bandmate Wyclef Jean and her label, which suggested bringing in Wu-Tang Clan’s mastermind, RZA.

The album was somewhere between R&B and hip-hop (and in fact was nominated and won in R&B instead of rap categories), and right off the bat, the album showcases Hill’s considerable skill as both a rapper and singer. The dancehall-inflected "Lost Ones" takes on an aggressive stance, with Hill rapping in Jamaican patois and invoking phrases of religious retribution, but it’s followed by a neo-soul breakup ballad, "Ex-Factor," featuring Hill’s signature throaty vocals.

The other major hits on the album besides "Ex-Factor" were "Doo Wop (That Thing)" and "Everything Is Everything," which cemented Hill as one of the best lyricists in hip-hop. Twenty-five years later, the whole album holds up beautifully and features some incredible invited guests.

Perhaps it’s not a coincidence that the first hip-hop album to break the Album Of The Year barrier was released in 1998 — when the genre had reached what is arguably its creative apex. With the incredible stylistic and regional diversity of that year’s albums, hip-hop had succeeded beyond its founders’ wildest dreams. 

Hip-Hop Just Rang In 50 Years As A Genre. What Will Its Next 50 Years Look Like?