The San Francisco Bay Area is a geographically and culturally diverse region of Northern California whose music scene has influenced the world. There is a lot more territory to Northern California, but the more than 7.5 million people who live in the Bay are crucial to the state's music scene.

While the Summer of Love and associated boom of rock and psychedelia in the 1960s might be the first thing that comes to mind when thinking of the sounds of San Francisco, the Bay has long been a source of creative, boundary-breaking hip-hop music and culture. The region's nine counties are where many definitive hip-hop acts were raised and became inspired to create.

Major labels largely ignored Bay Area artists at the beginning of hip-hop's golden age. However, that lack of attention allowed for wider creative freedom and a bevy of distinctly Bay Area sounds. 

As hip-hop celebrates half a century of soundtracking the world, it’s a good time to learn how this part of the West Coast fits into this global culture — and how it stands out. Listen to Spotify playlist below or visit Amazon Music, Pandora and Apple Music to learn more about the Bay Area's bountiful hip-hop culture.

A Brief History Of Bay Area Hip-Hop

The Bay Area's first local commercial rap release came in 1981 via Motorcycle Mike’s "Super Rat." But the world wouldn’t become seriously acquainted with Bay Area rappers until the early ‘90s, when MC Hammer told everyone what they couldn’t touch.

Some of the most notable releases tap into the region's educated and aware, activist-oriented, health-focused lifestyle. The Bay also knows how to party, and the funky musicality of the region — from Sly and the Family Stone to Con Funk Shun (whose member Felton Pilate produced some of MC Hammer’s early works) — have been a strong influence on hip-hop culture nationwide.

However, the Bay Area rap music scene is historically distinguished by reality-based work that sometimes alludes to criminal activity — including violence, murder, drug dealing and sex trafficking — and details rough times. 

The intermingling between the fictional world of music and criminal realities has led rap lyrics to be used against defendants in criminal cases around the country. In the '90s and early aughts, prominent rappers such as Sacramento’s C-Bo and Vallejo’s Andre "Mac Dre" Hicks were jailed for their lyrics, which detailed crimes and had anti-police and governor sentiment.  

New state legislation is setting a national example for such work to be inadmissible in court. In September, with the support of popular Bay Area rappers E-40 and Too $hort, California Gov. Gavin Newsom signed the Decriminalizing Artistic Expression Act to restrict the use of rap lyrics in criminal proceedings. (The Recording Academy is also involved in a federal effort to limit the use of lyrics in court.)

Several high-profile murders and deaths altered the trajectory of burgeoning careers, casting a question mark about the unrealized potential of some of the Bay Area’s brightest artists. This unfortunate list includes the 1996 Las Vegas murder of Tupac Shakur — who spent formative years being educated and recording in the Bay Area — and Mac Dre, the progenitor of the region’s hyphy culture who was shot to death in Kansas City in 2004 and still reigns as the Bay Area’s biggest posthumous figure. Pittsburg’s Dominick "The Jacka" Newton is another revered figure supported heavily by Northern California who was killed in Oakland in 2015. In 2021, Stephen "Zumbi" Gaines from Zion I died in an Oakland hospital; his death was ruled a homicide, yet no criminal charges have been filed and his family called to continue the investigation in 2022. 

Bay Area hip-hop has had a few moments to shine especially bright in the eyes of the world, but the local scene has kept grinding in and out of the mainstream spotlight. Sporadic attention and contracts from the major record labels throughout the years meant that the Bay Area rap scene generally needed to continue to be sustained independently. 

In the pre-streaming era, record stores such as Amoeba Music in San Francisco and Rasputin Music (which had several locations at its height) sold thousands of copies of albums and mixtapes from local artists on their own. Too $hort and E-40’s DIY business model would influence Southern rap moguls like Percy "Master P" Miller, who started his No Limit Records in Richmond, California, and Bryan "Baby" Williams of New Orleans’ Cash Money Records.

For decades, there was an absence of prolonged label and distribution support from the traditional music business centers of Los Angeles, New York City and, later, Atlanta. A significant shift began when EMPIRE Distribution opened in San Francisco in 2010, making the city a power player in the international music industry.

While the San Francisco Bay Area may not be the biggest name in the national hip-hop conversation, its underdog status is a point of pride and reason for continued creativity. In 2023, hip-hop artists, producers and businesspeople keep an eye on the Bay for lyrical, linguistic, music, dance and style trends.  

Definitive Artists In Bay Area Hip-Hop

MC Hammer: Stanley Burrell’s evolution from young bat boy for the Oakland Athletics and growing up connected to the streets, to becoming the GRAMMY-winning and Billboard-charting pop superhero MC Hammer is the Bay Area’s first international hip-hop success story. He’s the only rapper from Northern California who had his own Saturday morning cartoon (Hammerman) on ABC — an epic achievement in the early '90s, when weekend programming for kids was still a household phenomenon. 

He was the first to work with major brands like Taco Bell and Sprite in an era when hip-hop didn’t have the attention of corporate America, like it does now. VH1 aired a biopic in 2001 and A&E commissioned a family reality series in 2009. There’s even a Hammer doll made by the toy company Mattel.

Digital Underground: Helmed by Gregory "Shock G" Jacobs and Ronald "Money-B" Brooks, Oakland’s mischievous party rap crew Digital Underground flirted with various Billboard singles and albums charts throughout the '90s and released six albums until Jacobs' untimely passing in 2021. 

The self-described "Sons of the P" drew from the well of the Parliament-Funkadelic world, sampling and interpolating George Clinton’s best-known riffs, ad-libs and freewheeling thoughts. Digital Underground’s two top 40 hits include "Kiss You Back" and "The Humpty Dance," the latter nominated for Best Rap Performance By A Duo Or Group at the 1991 GRAMMYs. "The Humpty Dance" introduced the character of Humpty Hump, which was another of Jacobs’ alter egos, but the group pretended like they were different people, sometimes enlisting Jacobs’ own brother to help further the prank on stage.

Tupac Shakur: Shock G and Money-B took a young Tupac Shakur under their wings, bringing him on tour as a roadie and dancer in 1990 and producing songs on his 1991 debut album 2Pacalypse Now. Shakur recorded half of his sophomore album in the East Bay, and later signed to Los Angeles labels Interscope and Death Row.

His mother, Afeni Shakur, reconnected with the Bay Area in the last years of her life and passed away on her houseboat in Sausalito, not far from Marin City, where Tupac lived in his high school years. History hasn’t viewed him as a strictly Bay Area artist, but the region is a crucial architect of his career.

Too $hort: Though he was born in Los Angeles and moved to the East Bay in his youth, Todd Shaw’s Too $hort character is synonymous with Oakland, its pimp culture and being the first to sell custom mixtapes on the streets. He turned his "out the trunk" ethos into a decades-long deal with Jive Records.

Despite threatening to retire in the mid-'90s, Too $hort continues to make music to add to his discography, which includes six platinum-selling albums, three gold albums and the enduring hyphy anthem "Blow The Whistle." He has collaborated with many rappers, including Tupac and the Notorious B.I.G., and on "Bossy," a top 20 hit for Kelis. Shaw represented the Bay Area at the 2023 GRAMMYs' tribute to hip-hop, and told PEOPLE that he was "really glad to be a part of it." 

E-40: Like Too $hort, E-40 (Earl Stevens) parlayed his independent record hustle into a contract with Jive Records that yielded gold and platinum-selling singles and albums. Both essentially created a playbook that was cited and followed by Southern labels such as No Limit and Cash Money. E-40’s storytelling prowess and gift for slanguage is delivered with impressive speed, and continues to influence MCs all over the world. He’s as deft at crafting party-starters like his hyphy hit "Tell Me When to Go" as poignant tales like "Zoom," which describes how life handed him nothing, but he transcended his circumstances to become a leader.

A community-minded philanthropist, he recently donated $100,000 to Grambling University, which he attended, to create the Earl "E-40" Stevens Sound Recording Studio on campus and inspire the next generation of artists. In recent years, he has applied his independent strategies to the food, wine and spirits industries, and will release a cookbook in November.

E-40 and Too $hort have recorded two albums together, and have since formed the northern half of the rap supergroup Mount Westmore, with Los Angeles natives Snoop Dogg and Ice Cube. Stevens will soon have a Bay Area street named after him called E-40 Way in Vallejo — just as Shaw received Too $hort Way in Oakland in December.

Mac Dre: Andre Hicks didn’t have a mainstream career like MC Hammer or Too $hort, but his influence on Bay Area music and culture as a progenitor and propeller of hyphy remains outsized. His music is rooted in the streets, but also party minded and musical, bridging a gap between the rough and serious and happy and intoxicated.

His mother Wanda Salvatto, who is nicknamed Mac Wanda, continued his Thizz Entertainment label after his still-unsolved 2004 murder in Kansas City, Missouri. She has built an extensive discography of posthumous and tribute albums and compilations.

Keak Da Sneak: After making noise in the mid-Nineties Oakland group 3X Krazy and later on his own, the rapper born Charles Kente Williams has earned his spot as a crucial Bay Area music and slang innovator. He’s credited with expressions like "fa sheezy," "yadidimean" and hyphy, the latter a contraction devised to describe his hyperactive tendencies. 

"I don’t think they know, that’s my word," he proclaims in the chorus of his quick-moving 2005 party hit "Super Hyphy." In 2017, Keak Da Sneak was shot eight times by an unknown assailant at a gas station in Richmond, California. Though he’s been using a wheelchair ever since, he remains active in the local scene, recently appearing at DJ and podcaster Dregs One’s History of Bay Area Hip-Hop day party in San Francisco.

Definitive Bay Area Hip-Hop Releases 

Too $hort - Life Is…Too $hort (1988)

As a rapper and character, Too $hort has transcended generations of Bay Area hip-hop fans, but the old-schoolers will still point to his fifth album, which broke him out of the region thanks to support in the form of a 1989 re-release from Jive Records. It delivers the bawdy, pimp boasting raps that he’s known for, but Life Is… also shows his less-known talents for keyboard and drum programming.

MC Hammer - Please Hammer Don’t Hurt ‘Em (1990)

MC Hammer’s third album Please Hammer Don’t Hurt ‘Em spent almost five months on top of the Billboard 200, and he is the only rap artist from Northern California to win GRAMMY Awards. With their hooky Rick James and Prince samples, respectively, the album’s hit singles "U Can’t Touch This" and "Pray" set a production standard that has been relied on pretty much ever since — whether in the most popular songs of P. Diddy’s Bad Boy Records catalog in the 1990s, or today’s social media hits by Latto and Coi Leray. 

In 1991, Please Hammer Don’t Hurt ‘Em was nominated for Album Of The Year, and he took home three golden gramophones for Best Rhythm & Blues Song and Best Rap Solo Performance for "U Can’t Touch This" and Best Music Video - Long Form.

Digital Underground - Sex Packets (1990)

DU’s platinum-selling debut album may be the Bay Area’s greatest concept rap album, a lascivious romp assisted by imaginary sexual enhancement pills years before Viagra was invented. Songs like "Freaks of the Industry," "Doowutchyalike" and "The Humpty Dance" brought fun and levity to the streets and households across America. 

"The Humpty Dance" was not only a top 20 pop hit and a No. 1 rap single; its undulating groove formed the backbone of countless pop, rap, R&B and drum and bass songs that later sampled it. Even the Spice Girls couldn’t resist using it for their 1996 song "If U Can’t Dance."

2Pac - 2Pacalypse Now (1991)

The majority of Tupac Shakur’s first two albums were made in the Bay Area: He recorded all of 2Pacalypse Now and half of his sophomore album Strictly 4 My N.I.G.G.A.Z… at Starlight Sound in the East Bay city of Richmond. 2Pacalypse Now shows how a descendent of the Black Panther Party reflects his history for the '90s. 

He worked with local producers — including Digital Underground’s Shock G, Raw Fusion and Big D The Impossible — on early anthems like "Brenda’s Got a Baby," "Trapped" and "If My Homie Calls." Though his posthumous discography is long, he would go on to release just two more albums before his murder in 1996: Me Against the World and the GRAMMY-nominated All Eyez on Me.

Del the Funky Homosapien - "Mistadobalina" (1991)

When he was a little kid, Del the Funky Homosapien designed the three-eyed face that became the logo of his Hieroglyphics crew and a worldwide symbol of Bay Area rap. "Mistadobalina," which he produced with Boogiemen and his cousin Ice Cube, was his breakout song. His confident and fun flow drew people into the Hiero world — which now includes an annual festival in Oakland — and it still sounds timeless.

RBL Posse - "Don’t Give Me No Bammer Weed" (1992)

The biggest group to come from San Francisco’s tough Hunters Point neighborhood and score a major label record deal, RBL Posse is best remembered for this ode to smoking quality cannabis from their debut album A Lesson To Be Learned. Members Hitman and Mr. Cee were both victims of gun violence, but their sonic calling card remains a local anthem.

N2DEEP - "Back to the Hotel" (1992)

Vallejo is most often associated with Mac Dre and E-40, but the city also birthed N2DEEP, the Latinx group that brought the sax-heavy rap song "Back to the Hotel" to No. 14 on the Billboard Hot 100. This song was everywhere in 1992, and has been due for a renaissance of appreciation.

Souls of Mischief - "93 ‘til Infinity" (1993)

Friends of Del the Funky Homosapien and fellow Hieroglyphics crew members, A-Plus, Opio, Phesto and Tajai are Souls of Mischief. "93 ‘til Infinity" remains their inspiring signature song, resonating sonically and lyrically across generations. The track has been sampled dozens of times by artists like J. Cole, Big K.R.I.T. and Tyga.

The Conscious Daughters - Ear to the Street (1993)

Released by Priority Records — the Los Angeles label that introduced venerable acts such as Funkadelic, N.W.A. and EPMD to the world — Ear to the Street gave a national platform to two smooth and streetwise rappers from Oakland who happened to be women: CMG (Carla Green) and the late Special One (Karryl Smith, who passed away in 2011). Their debut album, and especially its breakout single "Somethin’ to Ride to (Fonky Expedition)," are still requisite car listening in the Bay Area.

Spice 1 - 187 He Wrote (1993)

Though he collaborated with Shakur, Spice 1 is still one of the more underrated and under the radar of the old-school gangster rappers. This sophomore album features production by Too $hort and local legends Ant Banks and E-A-Ski, as well as guest spots by E-40 and Compton’s MC Eiht. 187 He Wrote topped the R&B/Hip-Hop Albums chart and No. 10 on the Billboard 200 chart.

Luniz - "I Got 5 On It (Bay Ballas Vocal Remix)" (1995)

Almost 30 years since its release, this ode to smoking weed by Oakland rappers Yukmouth and Numskull still makes frequent appearances at Bay Area events and clubs. The Bay Ballas Vocal Remix, which features E-40, Richie Rich, Spice 1, Dru Down, Shock G, hogged all the attention back in the day and is still the version to play.

DJ Shadow - Endtroducing (1996)

The mysterious DJ and producer mixed at the nucleus of the SoleSides crew, which later became the Quannum Projects label and includes vital Bay Area artists like Blackalicious, Lyrics Born and Lateef The Truthspeaker. Shadow’s debut album Endtroducing is a masterpiece of instrumental hip-hop.

Hieroglyphics - 3rd Eye Vision (1998)

Oakland’s Hieroglyphics is made up of solo MCs and groups who have created some of Bay Area rap’s most vaunted songs. The first of three crew albums, the stellar arrangement and song selection on the 22-track 3rd Eye Vision, which refers to their three-eyed logo and spotlights each individual’s talents, keeps it in the conversation 25 years since its release.

Blackalicious - "Alphabet Aerobics" (1999)

A stunning feat of linguistic excellence by the late rapper Gift of Gab (who tragically passed away in 2021 after receiving a kidney implant the year before), "Alphabet Aerobics" pushes rhymes of increasing complexity from A to Z. It’s a textbook of how to MC in one track.

Mystic - Cuts for Luck and Scars for Freedom (2001)

Mandolyn Wind Ludlum is best known as Mystic, a singer, rapper and educator from Oakland whose debut album sounds as fresh as when it was released in 2001. Cuts for Luck was re-released 10 years later in large part to the lead single "The Life" and "W," a duet featuring Fresno rapper Planet Asia that was nominated for Best Rap/Sung Collaboration at the 2002 GRAMMYs.

Charizma & Peanut Butter Wolf - Big Shots (2003)

Murdered in 1993, South Bay rapper Charizma never got the chance to see where his talent would take him. Big Shots was not released until 2003, but his flows on songs like "Methods" and "Jack the Mack" are timeless. Peanut Butter Wolf —a San Jose native producer and close friend of Charizma — moved his record label Stones Throw to Los Angeles and keeps Charizma's legacy alive.

Mac Dre - Treal TV DVD and Soundtrack (2004)

Thanks to the continuation of his Thizz Entertainment record label after his 2004 murder, Mac Dre’s posthumous discography is extensive, but a DVD released when he was alive is perhaps the most coveted release in the collection. Treal TV has a cult following for its casual depiction of his everyday life, car collection and live footage of him performing songs such as "Thizzelle Dance," which also appears on Dre’s 2002 album Thizzelle Washington. 

There’s also a CD soundtrack version of Treal TV featuring various artists and associates; a second volume of Treal TV was released in 2006 and includes footage of Mac Dre on the road in Hawaii. 

Mistah F.A.B. - "Super Sic Wit It" (2005)

With his Dope Era clothing store and frequent community events, Oakland’s Mistah F.A.B. has been an entrepreneurial and philanthropic leader in the scene since he turned out hyphy club and radio hits like "Super Sic Wit It." The high energy song for car sideshows helped him score a major label contract.

E-40 - My Ghetto Report Card (2006)

E-40’s many albums have consistently good arrangement and a narrative arc of storytelling, and My Ghetto Report Card represents him at the crest of a second wind that floated him into greater international recognition. Produced by Lil Jon, the lead single "Tell Me When to Go" landed at No. 35 on the Billboard Hot 100 and remains one of the big hits of the hyphy era. 

Atlanta’s king of crunk produced seven additional songs on the album, including "White Gurl" featuring UGK and Juelz Santana and "U and Dat" featuring T-Pain and Kandi, while Bay Area standard-setter Rick Rock and E-40’s son Droop-E rounded out the production duties.

The Coup - Pick a Bigger Weapon (2006)

The Coup represented the revolutionary side of Oakland with razor-sharp intellect and furiously funky beats. Pick a Bigger Weapon was released by Epitaph Records, a label known more for rock than rap music, and includes collaborations with Jello Biafra of Dead Kennedys and Tom Morello from Rage Against The Machine. Frontman Boots Riley has made forays into film and streaming TV, most recently with the comedy series "I’m a Virgo." The Coup’s late DJ, Pam The Funkstress, was selected by Prince to open some of his final shows.

Zion I - "Tech $" (2017)

Oakland’s Zion I has long reflected on the changes and realities of the Bay Area in their music. Nowhere does this resonate the most as it does on "Tech $," which details displacement and gentrification as it was literally happening to the late MC Stephen Gaines, who was known as Zumbi and Baba Zumbi. The accompanying music video shows him moving his family out of their house and out of the area.

Stunnaman02 - "Big Steppin’" (2021)

Perhaps the biggest local rap song to come out of the pandemic, San Francisco rapper Jordan "Stunnaman02" Gomes even got the city’s mayor to do the song’s infectious associated dance, which KQED calls "a trend that rhythmically mimics the act of bench pressing."

Bay Area Hip-Hop Subgenres & Styles 

Bay Area rap can be educated, activist, party-starting and gangster — and sometimes all on the same track. There’s a distinct pride in the scope and the range of subject matter and sonic aesthetics in the region. Achieving uncategorizable moments is wonderful, but everyone seems to love big, trunk-rattling bass. 

There’s always been nuance within these major styles — for example, music that could blanketly be called gangster could also be subdivided into general topic styles such as pimping and drug dealing, and even small subgenres like mobb music — which was coined to describe a particular sinister and gritty sound characterized by even heavier basslines more than the lyrical content.

Turntablism: In the '90s Bay Area DJs with mobile party and technical battle circuit experience contributed significantly to the development of turntablism. With the help of the Return of the DJ compilation series from San Francisco’s Bomb Hip-Hop Records, turntablism became an international style of using and manipulating record players like musical instruments to record original works. With talents such as Shortkut, DJ Disk, DJ Apollo, DJ Flare, D-Styles, Qbert and Mix Master Mike, local crew Invisibl Skratch Piklz won world battle championships and inspired countless fans to become DJs. Mix Master Mike has toured extensively with Beastie Boys, Metallica and Cypress Hill.

Hyphy: The aughts ushered in the music, linguistic and car subculture called hyphy, bringing in quicker tempos ready for popping pills and "going dumb" on the dancefloor. Too $hort would criticize the abuse of MDMA in his 2006 hit "Blow the Whistle," but most of hyphy’s hits revel in ignorance — and Mac Dre certainly touted the benefits of ecstasy when he was alive. 

Almost 20 years since hyphy’s ascent and this is thought of as a sort of golden era of Bay Area hip-hop, a time when the world’s attention was facing west. Hyphy songs have been sampled in more contemporary contexts (as Saweetie used "Blow the Whistle" for 2020’s "Tap In"), and the subject is a common one used to evoke an uplifting nostalgia.

Based: Brandon "Lil B" McCartney formed the rap group the Pack while attending  Berkeley High School, and their 2006 cult hit "Vans" led to an album deal with Jive Records. After leaving the Pack, Lil B single-handedly propagated an unedited and free associative style he called based, dubbing himself the Based God. He was the first in the area to use social media sites and apps to become an early meme, which he supported with a large quantity of songs and videos.

Rising Bay Area Rap Artists

The next generation of artists leading the future of the Bay Area is tapping into the technological prowess of the region while furthering traditions of musical innovation and philanthropic goals. While Bay Area rap has long been male-dominated, the future may be more balanced.

Larry June: Ten albums deep, Larry June is not exactly new to this, but he’s the San Francisco artist who is currently breaking through to the world with his album Spaceships on the Blade. Northern California’s healthy, organic lifestyle is a popular topic for June, who eats well, owns a boba shop and is showing his fans the benefits of consistent, hard work.

P-Lo: After years producing for the Bay Area’s HBK Gang artists as well as national stars such as Wiz Khalifa and Yo Gotti, P-Lo’s status as a solo artist is on the rise with his 2022 album STUNNA. His 2022 collab with Larry June, "Doing Good," is a uplifting banger

Lil Kayla: Born and raised in San Francisco, 24-year-old Lil Kayla is signed to Atlantic and repping for the 415 on her freestyles, singles and 2022 album Young & Turnt. "I’m about to do it for my city," she said in a May interview with Lil Blood TV. "I’m gonna be the one to do it, 'cause everybody else, they get it and they leave and they don’t come back. I’m not going nowhere."

LARussell: Born LaRussell Thomas, Vallejo’s LARussell has harnessed social media to spread his sharp rhymes, as well as his social message. He donates money to allow his community to enjoy  restaurant meals they may not otherwise be able to afford. Freestyles for Sway and the Breakfast Club and his album I Hate When Life’s Going Great have solidified his name outside the region.

MacArthur Maze: Teamwork makes the dreamwork, and there’s hope that MacArthur Maze, the Oakland collective of MCs and producers led by Golden State Warriors DJ D Sharp, will help usher in a fresh era of working together for the creative good in the Bay Area, as evidenced on the new group album Blvck Saturday.

Su’Lan: This Richmond-based duo describe themselves as having "pretty girl swag with a hood twist" flip old crunk and hyphy hits into fresh new favorites on their debut album Forever Da Gang.

TotogangzMau: A female Samoan rapper from East Palo Alto, TotogangzMau is showing lyrical greatness and melodic hooks out the gate on autobiographical songs like "Grow Up."

Notable Northern California Neighbors

The Bay Area’s sky high rents and home prices have steadily driven residents to the Central Valley, which includes cities like Modesto, Stockton and California’s capital city of Sacramento, and effectively stretched the geographical and sociological boundaries of the region.

Sacramento produced a bounty of homegrown gangster rappers. The most notable are C-Bo, a 2Pac collaborator who was jailed in 1998 for his anti-police and governor lyrics; Marvaless, a woman who debuted with C-Bo and went on to release several solo albums and collaborations with Bay Area rappers Messy Marv, Husalah and The Jacka; and Mozzy, a contemporary star from the Empire Distribution crew. The region also claims Saweetie, the "Icy Girl" who has been endorsed by McDonald’s and is signed to Warner Records; she grew up in the East Bay city of Hayward before moving to Sacramento.

After a spate of violent incidents at major hip-hop concerts led Oakland to ban rap shows for a year in 1989, the Bay Area’s biggest cities developed a reputation for being averse to the genre. Sacramento, Stockton and Modesto have served as more consistent markets for a number of Bay Area rappers, especially those with more violent or drug-related content.

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

Coolio was living in the "Gangsta's Paradise" of his own creation when the 1996 GRAMMY Awards rolled around. The year before, the ode to hip-hop culture had not only become a global No. 1 hit for the rapper, but also the best-selling song of 1995 in the U.S. And that February night in Los Angeles' Shrine Auditorium, the track won Coolio his first GRAMMY, for Best Rap Solo Performance.

Receiving the trophy from Salt-N-Pepa and Mary J. Blige (clad in head-to-toe leopard print), the rapper emerged from backstage with his overjoyed entourage in tow, and started out his acceptance speech by claiming his GRAMMY "for the whole hip-hop nation."

"West Coast, East Coast, worldwide — united we stand, divided we fall. Recognize," he continued before going on to thank God, his then-fiancée Josefa Salinas and his kids, as well as Stevie Wonder, Quincy Jones, his collaborator L.V., Michelle Pfeiffer (who starred in the song's music video) and others.

Coolio then ended his remarks on a serious note, acknowledging, "We've had a lil' problem lately in high schools and I only got one ting to say to all my Black and Latino brothers out there fightin': Ain't no gangsters living in paradise." 

During the telecast, Coolio also took to the stage to perform "Gangsta's Paradise," which had earned a second nomination for Record of the Year. (That major award ultimately went to Seal's "Kiss From a Rose," along with Song of the Year.)

Sadly, the gangsta rap pioneer died in September 2022 at age 59 after suffering an accidental overdose laced with fentanyl. Press play on the video above to revisit Coolio's GRAMMYs win and check GRAMMY.com for more new episodes of GRAMMY Rewind.

50 Artists Who Changed Rap: Jay-Z, The Notorious B.I.G., Dr. Dre, Nicki Minaj, Kendrick Lamar, Eminem & More

Lil Wayne had already hit a new high point when he released "A Milli" in the winter of 2008. "Lollipop," the single that directly preceded "A Milli," had scored the rap legend his first hat trick by hitting No. 1 on the Billboard Hot 100, Hot R&B/Hip-Hop Songs and Hot Rap Songs charts.

With "A Milli," the rapper born Dwayne Carter Jr. continued his chart-topping success by capturing yet another No. 1 on the latter two tallies and winning him the GRAMMY for Best Rap Solo Performance at the 2009 ceremony. The modern classic also heralded Wayne's blockbuster album Tha Carter III, which became the final album of the decade to sell more than a million copies in its opening week.

In this new episode of Hip-Hop Re:Defined, rising rap star Armani White tackles Wayne's noughties smash, with the Philadelphia-born newcomer building his flow over the same stuttering sample of A Tribe Called Quest's "I Left My Wallet in El Segundo" as the original.

"A millionaire/ I'm a West Philly millionaire, tougher than Nigerian hair/ My criteria compared to your career just isn't fair," White raps, personalizing the lyrics with a shout-out to his hometown while still echoing Weezy's trademark cadence.

In May, White dropped his major-label debut, Road to Casablanco, with the EP led by his viral single "BILLIE EILISH" and its official remix featuring Ludacris, Busta Rhymes and N.O.R.E.

Press play on the video above to watch White rip through "A Milli," and check back to GRAMMY.com for more new episodes of Hip-Hop Re:Defined.

K-Pop's Hip-Hop Roots: A History Of Cultural Connection On The Dancefloor

"We done split it down the middle so you can see both the visions," raps Big Boi on "Tomb of the Boom," one of the highlights from Outkast's 2003 magnum opus. And he wasn't kidding.

Essentially two solo albums for the price of one, Speakerboxxx/The Love Below saw Atlanta's premier hip-hop duo take the creative reins for one disc each, resulting in a whopping 135 minutes and 40 tracks of genre-hopping genius.

Favorably compared with classic double albums such as Prince's Sign O' The Times, Pink Floyd's The Wall and the Beatles' The White Album, the follow-up to 2000's Stankonia enjoyed similarly super-sized success, too. It topped the Billboard 200 for seven weeks on its way to worldwide sales of 11.4 million, spawned two No. 1 hits and picked up six nominations at the 2004 GRAMMY Awards — which resulted in three wins, including the coveted Album Of The Year.

And a full 20 years on from its Sept. 23, 2003 release, Outkast's fifth studio effort still stands up as a fearless, funkadelic and forward-thinking body of work. Below, take a look at 10 reasons why Speakerboxxx/The Love Below still has the power to get us all shaking it like a Polaroid picture.

It Helped Outkast Join An Exclusive Chart Club

Only 14 acts in the history of the Billboard Hot 100 have knocked themselves off the top spot. And Outkast joined that illustrious group — which also now includes the likes of Drake and Taylor Swift — in 2004 thanks to two of the era's most addictive hits.

The Little Richard-goes-power pop of "Hey Ya!" was the first to reach the summit, spending nine weeks there between December 2003 and the following February. And then it was finally dislodged by the brassy Southern hip-hop of Sleepy Brown collaboration "The Way You Move," which enjoyed just seven days in pole position before Twista's "Slow Jamz" put an end to the Outkast stranglehold.

It Doubled Outkast's GRAMMY Count

By 2004, Outkast were no stranger to the GRAMMY Awards. They'd picked up Best Rap Performance by a Duo or Group for "Ms. Jackson" and Best Rap Album for Stankonia in 2002, and then emerged victorious in the former category again a year later for "The Whole World." But it was the 2004 ceremony where they truly reigned supreme.

The duo stole the show with two memorable performances. First, Big Boi performed "The Way You Move" in a star-studded Funk Music Tribute, which also included legends George Clinton, Earth Wind and Fire and Robert Randolph. Later, André 3000 closed out the show with a celebratory rendition of Best Urban/Alternative Performance winner "Hey Ya!"

The "Hey Ya!" performance was a fitting end to the night indeed, as the pair took home the final — and most prestigious — award: Speakerboxxx/The Love Below was crowned Album of the Year. (It also won Best Rap Album earlier that evening.)

It Spawned Several Classic Videos

Outkast had always been a visual hip-hop outfit, but their videography undeniably peaked with the Speakerboxxx/The Love Below campaign. "Hey Ya!" deservedly picked up four MTV Video Music Awards thanks to its inspired tribute to the Beatles' debut on "The Ed Sullivan Show" — and André 3000's portrayal of all eight of the fabulously named musicians in the video, including guitarist Johnny Vulture and drummer Dookie Blossom Gain III.

Also directed by Bryan Barber, the "The Way You Move" video saw Big Boi showcase his lyrical flow in everything from a rim shop and old-school music hall to dojo and safari retreat. "Roses," meanwhile, finally allowed both members to share the screen as warring members of rival high school crews in a tongue-in-cheek homage to West Side Story.

It Boasts An Impressively Diverse Guest List

Big Boi roped in several usual suspects on Speakerboxxx, including Big Gipp on "Tomb of the Boom," Killer Mike on "Bust" and Cee-Lo Green on "Reset," while also securing the talents of heavy hitters like Jay-Z, Ludacris and Lil Jon and the East Side Boyz. While an undeniably impressive guest list, André 3000's choice of collaborators was even more intriguing.

Shortly before teaming up with the rapper on her own track "Millionaire," Kelis lent her signature husky tones to the appropriately creepy funk of "Dracula's Wedding." Hot on the heels of Come Away with Me, Norah Jones provided the necessary sultriness on the acoustic "Take Off Your Cool." And perhaps most unexpected of all, Hollywood actress Rosario Dawson proved her diva credentials on the metallic funk of "She Lives In My Lap." The Love Below's roll call was yet another sign that Outkast weren't interested in playing by hip-hop's rules.

It Samples Wisely

Considering Speakerboxxx/The Love Below consists of 40 different tracks and clocks in at nearly 135 minutes, it's surprising that Big Boi and André 3000 only relied on a handful of samples. And like their choice of collaborators, they're far from obvious, either.

Who knew that The Sound of Music showtune "My Favorite Things" would work as a drum and bass instrumental? Or that Timmy Thomas' one-hit wonder "Why Can't We Live Together" and the sensual New Jack Swing of Aaliyah's "Age Ain't Nothing But a Number" would fit perfectly as on "Pink and Blue"?

Elsewhere, the propulsive electronic hip-hop of opener "Ghetto Musick" borrows from Patti LaBelle's '80s soul jam "Love, Need and Want You," while "She Lives in My Lap" lifts from both Geto Boys' "Mind Playing Tricks on Me" and Volume 10's "Pistolgrip-Pump."

It Paved The Way For Genre-Hopping

While genre boundaries have been well and truly broken down in today's streaming era, back in 2003, most major artists stayed in their lane — but not Outkast.

The Love Below certainly has little regard for pigeonholing, veering from big band crooning ("Love Hater") to celestial neo soul ("Prototype") to twitchy electro ("Vibrate") with both confidence and panache. The more-focused Speakerboxxx also keeps listeners on their toes, whether it's with the squelchy P-funk of "Last Call," punchy rap-rock of "Bust" or the mariachi-tinged hip-hop of "The Rooster."

Despite its mammoth running time, the album impressively never repeats itself, providing more flashes of invention than most of the duo's peers manage in an entire career.

Even The Interludes Are Inspired

Of Speakerboxxx/The Love Below's 40 tracks, 11 could be classed as interludes — a number that would normally draw groans, especially considering how much they're often the bane of a hip-hop album. But while the blink-and-you'll-miss-it contribution from comedian Henry Welch ("D-Boi") and the brief helium-voiced reprise of "Bowtie" are rather pointless, the majority of the breathers do add something to the record.

"Interlude" is a hypnotic spoken word piece which offers a crash course in Outkast history ("Believe in the dirty Southernplayalisticadillac-funky-ATLiens/ Together, makes Aquemini"). "The Love Below (Intro)" is a sumptuous orchestral number in which André 3000 throws things back to the Rat Pack. And "God (Interlude)" finds the latter living up to his horndog reputation in a cheeky prayer recited over some sun-dappled guitars.

It's About Both Love And War

As titles such as "Happy Valentine's Day," "Behold a Lady" and, of course, The Love Below would suggest, André 3000's half of the album is largely focused on the affairs of the heart — no doubt informed by his break up from Erykah Badu and subsequent quest to find 'the one.'

But to counterbalance all the love talk, Speakerboxxx is a more socially-conscious record in which Big Boi tackles themes of spirituality, philosophy and politics, none more so than on "War," a fervent protest song which no doubt left George W. Bush's ears burning ("Basically America, you got f—ed/ The media shucked and jived, now we stuck, damn.")

The Pair Deliver Career-Best Vocals

Free from having to battle for space on the same track — they only appear together on "Ghetto Musick," "Knowing" and "Roses" — Big Boi and André 3000 have arguably never sounded better than on their respective discs.

The former is in particularly ebullient form on his alter ego Sir Lucious Left Foot's origin story "Unhappy," and also spars well with hip-hop giants Jay-Z and Ludacris on "Flip Flop Rock" and "Tomb of the Boom," respectively. His regular partner in crime, meanwhile, appears to relish channeling his inner Prince on the falsetto-led "Spread" and final single "Prototype."

It Helped Revive The Hip-Hop Double Album

The mid-'90s had been a boom period for the hip-hop double album, with Tupac Shakur's All Eyez on Me, Notorious B.I.G's Life After Death and Wu Tang Clan's Wu Tang Forever regarded as the holy trinity. But the concept had fallen out of favor until Outkast's Speakerboxxx/The Love Below shifted nearly six million copies in the United States alone.

Following its triumph, Nas (2004's Street's Disciple), UGK Underground Kingz (2007's Outkast-featuring Underground Kingz) and Tech N9ne (2008's Killer) all got in on the act. More recently, Vince Staples (2015's Summertime '06), Drake (2018's Scorpion) and Kendrick Lamar (2022's Mr. Morale & The Big Steppers) have also tried to bottle lightning twice. But while they all have their high points, none quite match up to the sheer brilliance of Outkast's crowning glory.

50 Artists Who Changed Rap: Jay-Z, The Notorious B.I.G., Dr. Dre, Nicki Minaj, Kendrick Lamar, Eminem & More

Although they might seem like disparate genres today, K-pop and hip-hop go way back. Their link can be traced to a single nightclub in Korea: Moon Night. 

Located in Seoul's Itaewon neighborhood, Moon Night wasn't particularly remarkable among the many other bars catering to tourists and American servicemen at the nearby military base. However, in the late '80s and early '90s, the club was ground zero for the genesis of the nation’s first K-pop group and the founding of the country’s "Big 3" music entertainment labels. 

Moon Night is so crucial to the development of K-pop as we know it today because the club played music beloved by its target clientele: Americans. And in the midst of hip-hop's golden age, hip Korean audiences got hooked.

Over decades, that connection to hip-hop has developed and evolved to create the juggernaut that is contemporary K-pop. Today, the influence of hip-hop can be seen in K-pop dance, dress and even instrumentation.

Pioneering K-Pop On The Dancefloor

Where nightlife in Korea was long separated by nationality — Korean citizens had their own establishments, as did U.S. military personnel — a new kind of integrated club scene blossomed in the 1990s. For the first time, Koreans could legally patronize the same bars as American G.I.s. 

Around 1 a.m., clubs like Moon Night would transition from a "normal Korean club" to a foreigner haven, recalls Dr. Michael Hurt, an Assistant Professor at the University of Suwon's International College.

That Moon Night became the Ur of K-pop as we know it was chiefly because Black American soldiers patronized the club, which played hip-hop. As Koreans and Black soldiers socialized, a new culture of hip-hop dance, or "rap dance," and music grew. Dr. Hurt experienced the eagerness with which young Koreans learned hip-hop moves while visiting Moon Night in the '90s. 

Dr. Hurt — who is Black and Korean and has been living in country for various periods since the mid-'90s — recalls clubgoers asking to dance with him. They would follow along with every step. While hip-hop music was important to the progenitors of K-pop, Koreans at the time were most fascinated by dance moves, and the emphasis on dance remains an important aspect of K-pop today. 

By the early '90s, hip-hop had begun to egress its original audience and evolve into a new form. The cross-cultural connection happening at Moon Night was replicated across Seoul; Dr. Hurt notes that Koreans and Black Americans also found common musical interest at Blue Monkey in Sincheon and Golden Helmet in Hongdae.

Future K-pop heavy hitters like Yang Hyun-suk of YG Entertainment, Park Jin-young of JYP Entertainment, and Lee Soo-man of SM Entertainment were rumored to have patronized Moon Night. However, Dr. Hurt theorizes that if they were in the club scene they also visited other places too.

K-Pop's First Generation Of Stars: Born At Moon Night, Shared Online 

While hip-hop was largely inaccessible to Koreans in the 1990s, there were always dedicated Korean listeners. This young, niche community consisted of members like Seo Taiji, who brought rap dance to the public and became K-pop's first stars. 

Seo Taiji and Boys reportedly learned how to dance from Black American soldiers at Moon Night. (Yang Hyun-suk, who later on became the founder of YGE, and Lee Juno were the "and Boys" component of the trio.) Their example laid the groundwork for the second generation of K-pop stars. 

"[Seo Taiji and Boys] were like gods on earth," recalls Dr. Hurt. 

The members became the undisputed purveyors of hip-hop in Korea, utilizing American hip-hop, metal and punk to create a unique musical fusion. The practice of mixing and melding genres is the standard in K-pop to this day.

Seo Taiji and Boys' 1992 performance of "난 알아요 (I Know)" on a competitive TV show struck a chord with the nation's youth, effectively introducing hip-hop to the general public. The performance also filled a capacious hole left in the Korean music industry after the roll back of Emergency Measure No. 9 (which only allowed patriotic or "healthy" songs to be broadcast), which banned hundreds of songs from the likes of Bob Dylan, Johnny Cash and Eric Clapton. Therein, Seo and company brought a new sound to the previously restricted airwaves. 

Still, a lesser-known idol predates Seo Taiji and Boys' rise by a couple of years. Once again, Moon Night remains in the backdrop.

If Seo Taiji and Boys is K-pop’s first idol group then Hyun Jin-Young is K-pop’s first solo artist. Though his career was brief, Hyun Jin-Young "is generally credited with bringing hip-hop to the mainstream in Korea," says Dr. Crystal Anderson, Associate Director of Engaged Learning and African and African American Studies at George Mason University. On hits like, "슬픈 마네킹 (Sad Mannequin)," Jin-young sang, rapped, and performed dance moves, such as the Roger Rabbit, over a hip-hop beat. "Without him, you wouldn't have [K-pop] idols, but at the same time, Seo Taiji showed that it could be lucrative and popular." 

Artists like Hyun Jin-Young, Seo Taiji, and, later, H.O.T were at the forefront of Korea's "rap dance" scene in the mid-to-late '90s. At the turn of the century, hip-hop culture began to circulate even further via the internet.

"The young hip-hop community [in Korea] has always been pretty hardcore because they had to be to even get enough information to maintain community," Dr. Hurt notes. "[Things] like what are the new fashions, you had to be deep into it."

Youth were largely responsible for disseminating the burgeoning sound of K-pop. "Music ​is ​not ​becoming ​popular ​at ​church. ​It ​starts ​from ​some ​kid ​pirating ​a ​CD," says Kirsten Keels, a 2021 Fulbright Korea scholar.  

Online, Koreans could explore hip-hop even further. In BTS’ book, Beyond The Story, RM recounted learning  about hip-hop through interviews and documentaries about rappers posted on YouTube as a teen. His interest in hip-hop would later cause a ripple effect that would lead him to his current position in BTS.

"Legitimizing" Hip-Hop In K-Pop's Second Generation

By the second generation of K-pop, which roughly begins in 2003, the days of "rap dance" had fizzled out in favor of a distinct K-pop sound. However, hip-hop’s presence in the genre remains in the form of creating a designated rapper in each idol group.

Korean Americans also played a significant role in the "legitimization" of hip-hop and K-pop. "In the early days of K-pop, particularly with the idol groups, you would have one or more members who were Korean American. The idea was they were closer to the source material and therefore it was more authentic," says Dr. Anderson. 

This rings true for K-pop groups like H.O.T — Lee Soo-man of SM Entertainment's first massively successful group —  and 1TYM, which had Korean American members. Both groups have been cited as inspiration for groups like BTS and 2PM. H.O.T's successful formula became the blueprint for many K-pop groups. They industrialized the K-pop system, much as Motown developed its artists and hit-making processes. 

Hip-Hop Artists And K-Pop Idols: Past And Present

Decades after its inception, K-pop and hip-hop acts continue to work together. In 2004, Snoop Dogg and Warren G hopped on Jinusean’s track, "2 All My People." The song's infectiously funky beat made the two rappers' appearance feel seamless.

In 2010, Kanye West was featured on JYJ’s "Ayy Girl" (West also appeared in the music video). And two years later, Psy, who has been a lifelong fan of M.C. Hammer, performed the rapper’s signature dance move next to him at the 2012 American Music Awards.

K-pop and hip-hop royalty came together in 2013 when BIGBANG’s G-Dragon and Missy Elliott gave a mesmerizing performance of "Niliria" on "M-countdown", a weekly music program broadcasted by M-net.  It was a legendary moment in K-pop history because it brought together two highly respected rappers from different countries.

One group in particular has a slew of hip-hop collaborations – BTS. It doesn’t come with much surprise, since the septet’s CEO has openly stated "Black music is the base" of their musical identity. BTS and its members have collaborated with the likes of Nicki Minaj, J.Cole, Wale, Desiigner, Juice WRLD, and Lil Nas X (with whom they performed at the 2020 GRAMMYs). Recently, Jungkook, the youngest member of the group, made his solo debut with the song "Seven" featuring Southern rapper, Latto. The song hit No. 1 on the Billboard Hot 100.

In 2017, Jay-Z signed former 2PM leader Jay Park (who takes his name from the multi-GRAMMY winner) to Roc Nation. The following year, Park was seen at Roc Nation’s annual brunch where he snapped pictures with the likes of Beyoncé and Big Sean. His debut EP, Ask Bout Me, featured rappers such as 2 Chainz, Rich The Kid, and Vic Mensa.

Hip-hop’s influence on K-pop runs through the genre’s past, present and future. K-pop and hip-hop artists have always had moments of mutual respect. Even at the most unsuspecting times, the two genres have always found ways to collaborate. 

Understanding Appropriation

However, the earnestness with which K-pop takes inspiration from hip-hop has understandably been questioned. The topic of cultural appropriation continues to be divisive, and unanimous consensus a rarity. "One person's appropriation isn't necessarily another person's appropriation," says Dr. Anderson. 

Lately, the conversation around cultural appropriation in K-pop is commonly in relation to visual signifiers. Instances where K-pop idols have been in the hot seat include but are not limited to: ATEEZ’s Hongjoong wearing cornrows in promo images, BLACKPINK’s Lisa sporting box braids on multiple occasions, and MAMAMOO’s Hwasa donning a durag. While there's often swift backlash from fans, response from record labels is typically delayed — if they acknowledge the uproars at all.

In 2019 and 2020, respectively, former CLC member Sorn posted a picture of someone dressed in a mask that resembled a racist caricature, while Stray Kids' Hyunjin imitated a Korean cartoon character that was reportedly based on Black racial stereotypes. The latter eventually issued an official apology, while Sorn continued to get into hot water — most recently for a photoshoot where she flaunted an afro. 

These recent cases are just repeat offenses of longstanding practices. In the '90s, JYPE Founder Park Jin-young put backup dancers in blackface and afros. The Bubble Sisters infamously wore blackface for their debut cover art and corresponding promo pictures in 2003. 

BTS' J-Hope raised eyebrows with his remake of Webstar and Young B’s 2006 track "Chicken Noodle Soup." The 2019 track featured Becky G, while J-Hope appeared with a gelled hairstyle that resembled dreadlocks. While the look bordered on appropriation, Young B praised the song in an interview with Billboard. 

"People of all cultures know the song," Young B said."[J-Hope and Becky G] made it even bigger for this day and age. I’m very open-minded and I feel like [the remake] is good for the culture. It was created in Harlem, and now it’s a worldwide thing."

"There’s a legit reason for people to be angry because aspects of African American culture have been and continue to be appropriated… the problem with Black popular culture is [it’s] so damn successful," Dr. Hurt says."[It’s] so hyper-successful that in a way you can't make restraining claims on it. I don't think it's at all realistic anymore." 

Cases of appropriation can get harder to identify when there seems to be no clear signs of foul 

play. RAIN and J.Y. Park’s 2020 duet, "Switch To Me," is redolent of Bobby Brown’s 1988 tune, "Every Little Step." The beat, clothing, and dance moves show that Park Jin-young was inspired by Brown. 

"My baseline for a negative appropriation and misappropriation is a racial performance that mocks or demeans," Dr. Anderson adds. "We need to recognize that there's another perspective, not necessarily to excuse some of the more egregious cases of negative appropriation,. We can't use our American racial lens and just put it over this thing and have it make sense because there are other factors at play."

Sometimes the boundaries are pushed too far and are met with legal contention. In 2004, first-generation K-pop group Baby V.O.X released "Xcstasy," utilizing a freestyle Tupac made while incarcerated. The group’s label founder, Yoon Deung Ryong, vehemently denied the rumors that they illegally used the late rapper’s voice and likeness. However, reports from that time failed to corroborate their label’s defenses. In 2020, "Cupid Shuffle" singer Bryson Bernard accused and threatened to sue K-pop group Seventeen for their song "Left & Right" which sounded comparable to his 2007 hit. 

Over the past three decades, hip-hop has become part of Korea’s public consciousness resulting in the K-pop we see and hear today. The spark that Black American GIs, Seo Taiji, and hip-hop-loving Korean youth lit has exploded into a billion dollar industry. Although it can come at the cost of misappropriation and well-meaning appreciation, it ultimately shows the influence of hip-hop and Black popular music around the world.

What's Next For K-Pop? A Roundtable Unpacks The Genre's Past, Present And Future