110 Fun Facts About 90s Hip Hop

Vice President Dan Quayle said which Tupac album 'has no place in our society'?

2Pacalypse Now: Quayle attacked it after a Texas state trooper was shot dead in 1992, a killing linked to the album.

Tupac's Me Against the World hit number one in 1995 while he was where?

In prison: he was serving time at Clinton Correctional Facility for sexual abuse, and he married Keisha Morris there that April.

Which double album was Tupac's first album for Death Row Records?

All Eyez on Me: it counted as two of the three albums in his Death Row contract, and he recorded it at a furious pace.

Under what alias did Tupac release The Don Killuminati: The 7 Day Theory?

Makaveli: Tupac took the name after reading Niccolò Machiavelli, saying he admired thinking that does whatever it takes to reach a goal.

Tupac was shot in a drive-by on September 7, 1996, in which city?

Las Vegas: earlier that night his entourage beat a Crips member in the MGM Grand lobby, and in 2026 that man's uncle, Duane Davis, was convicted of the murder.

The Notorious B.I.G. borrowed his alias 'Biggie Smalls' from a character in which 1975 film?

Let's Do It Again: in the film, two lodge brothers hypnotize an underdog boxer, bet on him with gangster Biggie Smalls, and win.

Biggie's 1994 single opening 'It was all a dream' is built on which 1983 track?

Mtume's 'Juicy Fruit': after 9/11 many radio stations cut the words 'World Trade' from the song, where Biggie had referenced the 1993 bombing.

Which R&B singer did Biggie marry in August 1994, weeks before Ready to Die came out?

Faith Evans: they met at a Bad Boy photo shoot, but the couple had separated by the time Biggie was killed in 1997.

The Notorious B.I.G. was murdered 16 days before the release of which album?

Life After Death: Biggie was shot as he left a crowded Los Angeles industry party that had been shut down early.

Which film's drug lord, Frank White, gave the Notorious B.I.G. one of his aliases?

King of New York: Christopher Walken played Frank White, and days before his death Biggie wore a plastic crown for a 'King of New York' portrait.

Which housing project did Nas grow up in before releasing Illmatic at age 20?

Queensbridge Houses: the Illmatic cover sets a childhood photo of Nas over the projects, and the now-classic album sold poorly at first despite rave reviews.

A Tribe Called Quest's 1990 single 'Can I Kick It?' is built on which Lou Reed song?

Walk on the Wild Side: Phife Dawg said the group saw no money from the single, because Reed claimed the profits from the sample.

Which 1996 Nas album brought in the Trackmasters to chase a more commercial sound?

It Was Written: to widen his audience, Nas also enlisted Lauryn Hill for the single 'If I Ruled the World'.

Wu-Tang Clan's debut album is named after Enter the Dragon and which other kung fu film?

The 36th Chamber of Shaolin: the group's own name came from another favorite of RZA and Ol' Dirty Bastard, the 1983 film Shaolin and Wu Tang.

What unusual clause did RZA win in the Wu-Tang Clan's Loud Records contract?

Solo deals with other labels: RZA wanted members spread across labels, so Method Man went to Def Jam while Ol' Dirty Bastard signed with Elektra.

The Chronic's cover pays homage to what?

Zig-Zag rolling papers: the album also made its guest rapper, Snoop Doggy Dogg, a star before he had released an album of his own.

How did Snoop Dogg get his nickname?

His mother thought he looked like Snoopy, the Peanuts beagle, and in 2012 a Rastafari priest in Jamaica gave him a new name, Snoop Lion.

Roughly how many copies did Snoop Dogg's debut Doggystyle sell in its first week in 1993?

About 800,000: Snoop was facing a murder charge over a shooting by his bodyguard, and a jury acquitted him of murder in February 1996.

Which label did Snoop Dogg join right after leaving Death Row?

No Limit: Master P's label released his next three albums, and in 2022 Snoop bought Death Row itself.

Death Row Records was founded in 1991 by Suge Knight, Dr. Dre, Dick Griffey and which N.W.A associate?

The D.O.C.: a 1989 car crash wrecked his rapping voice, so he kept working behind the scenes as a writer with Dr. Dre.

Sean Combs founded Bad Boy in 1993 after being fired from which label?

Uptown: Andre Harrell fired Combs in 1993, and Combs took the Notorious B.I.G. with him to his new label.

In 1995 Suge Knight invited artists to 'come to Death Row' if tired of their executive producer doing what?

Appearing in all their videos: the jab at Puff Daddy publicly escalated Death Row's feud with Bad Boy.

Tupac blamed Biggie and Puffy for the November 1994 shooting at which New York studio?

Quad Studios: Biggie's 'Who Shot Ya?', released months later, sounded to Tupac like mockery of the attack, and he answered with 'Hit 'Em Up'.

Andre 3000's line 'The South got something to say' was a response to what?

Boos at an awards show: the New York crowd jeered OutKast as they collected an award in 1995, and André answered them from the stage.

Which civil-rights icon sued OutKast in 1999 over a song title on Aquemini?

Rosa Parks: her lawyers argued the song borrowed her name without being about her, and the dispute dragged on until a settlement in 2005.

Jay-Z's 1996 debut Reasonable Doubt appeared on which label he co-founded with Damon Dash and Kareem Burke?

Roc-A-Fella: rejected by the major labels, Jay-Z, Damon Dash and Kareem Burke started their own label to put out his debut.

Which unlikely artist did the Fugees sample on their 1996 single 'Ready or Not'?

Enya: the Fugees used her 1987 song 'Boadicea' without asking, and she came close to suing before they reached an agreement.

The Miseducation of Lauryn Hill (1998) was the first hip hop record to win what?

The Album of the Year Grammy: accepting it from Whitney Houston, Hill marveled on stage that a hip hop record had won.

Which lead single from The Miseducation of Lauryn Hill topped the Hot 100?

Doo Wop (That Thing): Hill wrote it as a warning to women and men alike not to let 'that thing' run their lives.

Coolio's 1995 smash hit interpolates which Stevie Wonder song?

Pastime Paradise: Stevie Wonder approved the interpolation only if Coolio took the curse words out, so it became one of his few clean songs.

Salt-N-Pepa won their first Grammy in 1995 with which single?

None of Your Business: Salt-N-Pepa had lost rap Grammys twice before, with 'Push It' and 'Let's Talk About Sex', both times to DJ Jazzy Jeff & the Fresh Prince.

In 1998 DMX released two albums that both did what?

Debuted at number one: earlier in the decade, Columbia had let DMX go after his single 'Born Loser' went nowhere.

DMX took his stage name from what?

An Oberheim drum machine: he started out beatboxing and, feeling he was 'nice with the beats', took his name from one of the era's best drum machines.

Which British singer's track is sampled on Eminem's 1999 breakthrough 'My Name Is'?

Labi Siffre: the openly gay singer refused to clear the sample until lyrics he called lazy bigotry against women and gay people were cut.

MC Hammer's Please Hammer, Don't Hurt 'Em was the first hip hop album to achieve what?

Diamond certification: Hammer earned an estimated $33 million in 1991 but filed for bankruptcy in 1996 with debts of nearly $14 million.

Which song's bassline did Vanilla Ice's 'Ice Ice Baby' borrow without credit?

Queen and Bowie's 'Under Pressure': the song began as the B-side of a 'Play That Funky Music' cover, and Queen and Bowie got credit only after it became a hit.

Which rap group released its second album, Black Sunday, in 1993?

Cypress Hill: that year they were banned from Saturday Night Live after a member lit a joint during their performance.

Bone Thugs-n-Harmony's 'Tha Crossroads' (1996) was a tribute to which figure who had signed them?

Eazy-E: the Cleveland group bought one-way bus tickets to California and phoned his label for weeks trying to land an audition.

Big Pun's Capital Punishment (1998) was the first album by a solo Latino rapper to do what?

Go platinum: earlier bids to name a Bronx street for him failed, but in 2021 the city named a Bronx corner Big Pun Plaza.

Which rapper was ousted from Nas's 1996 supergroup with AZ and Foxy Brown?

Cormega: he fell out with Nas over his dismissal, but they made up, and he rejoined the original lineup on Nas's 2020 album King's Disease.

Fab 5 Freddy was the first host of which rap video show?

Yo! MTV Raps: MTV aired the 1988 pilot as an experiment, but it drew some of the network's best ratings and became one of its most popular shows.

Coolio's 1995 smash with L.V. was the lead single from which film's soundtrack?

Dangerous Minds: when 'Weird Al' Yankovic parodied the song, Coolio refused his blessing and publicly objected, though the two later made peace.

Missy Elliott's blow-up suit in 'The Rain (Supa Dupa Fly)' was widely compared to what?

An inflated trash bag: Missy later joked on Twitter that it was never a trash bag but a patent leather blow-up suit.

Puff Daddy's 1997 Biggie tribute 'I'll Be Missing You' is built on which Police song?

Every Breath You Take: Combs never asked Sting's permission to use it, so Sting was able to claim 100 percent of the song's publishing royalties.

Will Smith's 1998 hit 'Gettin' Jiggy wit It' samples which Sister Sledge song?

He's the Greatest Dancer: rumors said Nas ghostwrote the rap, but Nas said Will Smith wrote it himself.

Which rap elder gave Busta Rhymes his stage name, borrowed from NFL receiver George 'Buster' Rhymes?

Chuck D: the name stuck as Busta broke out with a scene-stealing verse on A Tribe Called Quest's 'Scenario', ahead of his 1996 solo debut, The Coming.

Rapper Master P spent ten days on which NBA team's training-camp roster in January 1999?

Charlotte Hornets: he made the camp roster once the lockout ended, then was waived on February 1, four days before the shortened season opened.

Which jazz double bassist did A Tribe Called Quest hire to play on The Low End Theory (1991)?

Ron Carter: he agreed only after warning Q-Tip to drop the cursing, saying he would be gone before they could spell the word 'exit'.

Which Wu-Tang member raps the opening verse on 1997's chorus-free posse cut 'Triumph'?

Inspectah Deck: a flood in RZA's basement studio destroyed the beats made for his solo debut, delaying the album.

During which singer's 1998 Grammy speech for 'Sunny Came Home' did ODB declare 'Wu-Tang is for the children'?

Shawn Colvin: ODB told the crowd he had bought expensive clothes expecting Wu-Tang Forever to win Best Rap Album, which went to Puff Daddy instead.

In Juice (1992), Tupac's first film role, he plays which of the four Harlem friends?

Treach, Money-B and Donald Faison had all auditioned for the part; Tupac only tagged along with Money-B, asked to read, and got 15 minutes to rehearse.

Which Broadway musical's children's chorus did Jay-Z sample for a 1998 hit single?

Annie: the sample began a lasting link to the show, and Jay-Z went on to produce the 2014 film adaptation of Annie.

Naughty by Nature's 1991 hit 'O.P.P.' is built on a sample of which Jackson 5 song?

ABC: the song's 'You down with O.P.P.?' chant became a national catchphrase in the 1990s.

Warren G's 'Regulate' (1994) rides a sample of which Michael McDonald song?

I Keep Forgettin': Warren G sampled it because his parents used to play that record, and finding it brought back good feelings.

Which producer discovered the teenage duo Kris Kross at an Atlanta mall in 1990?

Jermaine Dupri: he spotted them at Atlanta's Greenbriar Mall, and he later stressed that the two boys weren't rappers or even trying to be.

Which DJ produced House of Pain's 1992 hit 'Jump Around'?

DJ Muggs. At University of Wisconsin home football games, students jump to it between the third and fourth quarters.

Which female rapper released the 1994 debut album Funkdafied?

Da Brat. In March 2020 she publicly came out on Instagram, confirming her relationship with businesswoman Jesseca Dupart.

Which Queen Latifah single from Black Reign won the 1995 Grammy for Best Rap Solo Performance?

U.N.I.T.Y. Latifah wrote it to confront the disrespect of women in rap and in society, from street harassment to abuse.

Which production team produced most of Ice Cube's 1990 solo debut, AmeriKKKa's Most Wanted?

The Bomb Squad. Cube turned to them after quitting N.W.A, angry at how little the group had paid him.

Pete Rock & CL Smooth's 'T.R.O.Y.' (1992) memorialises a dancer from which group?

Heavy D & the Boyz lost dancer Trouble T Roy in 1990, after he fell from a ramp at their show in Indianapolis.

Which funk star won his only Grammy as a credited co-writer of MC Hammer's 'U Can't Touch This'?

Rick James sued for a songwriting credit because the hit loops the riff from his 1981 single 'Super Freak'. The credit paid off when the track won Best R&B Song in 1991.

Which future Oscar-nominated actor topped the Hot 100 in 1991 as frontman of the Funky Bunch?

Mark Wahlberg rapped as Marky Mark on 'Good Vibrations', a number one single in 1991. The follow-up, 'Wildside', reached number ten before he swapped music for film roles.

Which NBA star released a hit rap album in 1993, a year after Orlando drafted him first overall?

Shaquille O'Neal reached number 25 on the Billboard 200 with Shaq Diesel, which shipped a million copies despite mixed reviews. He went on to release three more rap albums.

Which future hitmaker, then an unknown protégé, wrote Teddy Riley's verse on the 1992 hit 'Rump Shaker'?

Pharrell Williams was discovered by Riley at a high school talent show, as the producer's studio stood right next to the school. He later found fame with the Neptunes.

A 1994 Supreme Court ruling protecting parody arose from 2 Live Crew's take on which Roy Orbison hit?

Oh, Pretty Woman was reworked by the group after the song's publisher refused a licence. The justices held that even a commercial parody can qualify as fair use.

LL Cool J slipped which rival clothing brand's hat into a Gap television commercial in the late 1990s?

FUBU gained mainstream fame from the stunt, in which the rapper also rhymed the phrase behind the brand's initials. The fuss ended up boosting both companies.

Which 1992 presidential candidate's rebuke of rapper Sister Souljah became a political catchphrase?

Bill Clinton criticised her remarks in a speech to Jesse Jackson's Rainbow Coalition. A 'Sister Souljah moment' now means a politician publicly rebuking an extreme voice on their own side.

Which music mogul founded Vibe magazine and helped bring The Fresh Prince of Bel-Air to television?

Quincy Jones launched Vibe in 1993 with Time Inc. A few years earlier he had met Will Smith at a party in his own home and challenged him to audition for the sitcom on the spot.

Which duo's 1993 smash 'Whoomp! (There It Is)' followed weeks after a rival group's near-identical single?

Tag Team spent seven straight weeks at number two on the Hot 100. Florida's 95 South had released 'Whoot, There It Is' weeks earlier, and both labels called the overlap a coincidence.

Kris Kross, the teenage duo behind the 1992 chart-topper 'Jump', famously wore their clothes in what way?

Backwards clothing was the pair's signature look. 'Jump' stayed on top of the Hot 100 for eight weeks, and the album it came from sold four million copies in the US.

Queen Latifah played magazine publisher Khadijah James on which 1990s sitcom set in Brooklyn?

Living Single ran for five seasons on Fox from 1993, following six friends in their twenties. NBC's Friends, built around a similar group of six, did not premiere until a year later.

The Fugees' 1996 hit 'Killing Me Softly' reworked a 1973 number one by which singer?

Roberta Flack later performed the song on stage with the trio, and their hit prompted a dance remix of her original. The remake topped the charts in 20 countries.

Ice Cube first acted on screen as Doughboy in which 1991 drama set in South Central Los Angeles?

Boyz n the Hood made John Singleton the youngest person, and the first African American, nominated for the Best Director Oscar. He wrote the role of Doughboy specially for the rapper.

Which rap duo, one of them known for a ten-inch hi-top fade, starred in the 1990 comedy House Party?

Kid 'n Play carried the film to a Sundance premiere, where it won two prizes. Co-star Martin Lawrence, then little known, later headlined a hit sitcom of his own.

Which comedian starred in CB4, the 1993 mockumentary spoofing gangsta rap and N.W.A?

Chris Rock played a suburban kid who poses as an ex-convict to sell records. The title stands for Cell Block 4, the prison wing where his fake group claims to have formed.

Which rapper and frontman of the metal band Body Count played an undercover cop in New Jack City?

Ice-T played detective Scotty Appleton, who infiltrates a drug lord's gang. He went on to play Detective Tutuola on Law & Order: Special Victims Unit for more than two decades.

Which Virginia beatmaker produced every track on Missy Elliott's 1997 debut album, Supa Dupa Fly?

Timbaland recorded the album with her in two weeks or less, and critics praised its futuristic sound. The pair had already written songs together for Aaliyah's album One in a Million.

Which West Coast style of slow grooves and whining synthesizers took off with Dr. Dre's The Chronic?

G-funk leaned on samples of 1970s Parliament-Funkadelic records, topped with a high-pitched synthesizer lead. Snoop Dogg's Doggystyle carried the sound on a year later.

Which Public Enemy hype man became famous for wearing oversized clocks around his neck?

Flavor Flav explained that he wears the clocks because time is the most important element. He co-founded the group in 1985 and later became a television personality.

Which R&B singer joined Method Man on a 1995 duet that won the Grammy for best rap duo or group performance?

Mary J. Blige sings the intro and chorus, which borrow from a Marvin Gaye and Tammi Terrell hit. The single peaked at number three on the Hot 100.

Which rap trio organised the first Tibetan Freedom Concert, held in San Francisco's Golden Gate Park in 1996?

Beastie Boys member Adam Yauch co-founded the Milarepa Fund, first set up to pay royalties to Tibetan monks sampled on the group's 1994 album Ill Communication.

Dr. Dre left Death Row Records in 1996 to found which label, later home to Eminem?

Aftermath was built as a boutique label favouring a few high-profile releases. Dre signed Eminem to it in March 1998 on the advice of Interscope co-founder Jimmy Iovine.

Which Philadelphia hip hop band, formed by Black Thought and Questlove, is known for playing live instruments?

The Roots took that live sound to television as the house band on Jimmy Fallon's late-night shows from 2009. The two founders met at a Philadelphia performing arts high school.

Fugees members Wyclef Jean and Pras Michel share family ties to which Caribbean country?

Haiti shaped even the trio's name, clipped from 'refugees', a word often thrown at Haitian-Americans as an insult. Jean was born there and moved to Brooklyn with his family at the age of nine.

The Geto Boys, the group behind 1991's 'Mind Playing Tricks on Me', put which Texas city on the rap map?

Houston was also home to the group's label, Rap-A-Lot Records, set up to promote Southern talent. The single climbed to number 23 on the Hot 100, the group's highest placing.

Which New Orleans rapper's 1999 single 'Bling Bling' pushed the jewellery slang into mainstream dictionaries?

B.G. released it from his album Chopper City in the Ghetto, and it became a top 40 hit. The word reached the Shorter Oxford English Dictionary in 2002 and Merriam-Webster in 2006.

Which future superstar joined Cash Money's Hot Boys at 14, the youngest member of the New Orleans group?

Lil Wayne had signed with the label at just 11 after being discovered by Birdman. The quartet reached number five on the Billboard 200 with the 1999 album Guerrilla Warfare.

Which rapper's unlicensed Gilbert O'Sullivan sample led to the 1991 ruling that reshaped hip hop sampling?

Biz Markie had looped the singer's 'Alone Again (Naturally)', and the judgment required every future sample to be approved by its owner. His next album was titled All Samples Cleared!

Which Bad Boy rapper announced in 1999 that he was quitting music to follow a calling from God?

Mase broke the news on New York radio station Hot 97. He became an ordained minister and stayed away from recording for five years.

Which Chicago rapper did Guinness World Records name the fastest in the world in 1992?

Twista, then billed as Tung Twista, was clocked at 598 syllables in 55 seconds. His rapid-fire delivery is known as the chopper style.

Which producer made up one half of the duo Gang Starr alongside the Boston-raised rapper Guru?

DJ Premier got the job by sending a tape of beats to the label Wild Pitch, at a time when he was known as Waxmaster C. Guru liked it and invited him to move to Brooklyn.

Which Queens duo of Prodigy and Havoc released the 1995 album The Infamous, featuring 'Shook Ones, Part II'?

Mobb Deep produced most of the album themselves after finding outside beats poor or overpriced. Q-Tip of A Tribe Called Quest, who had discovered the pair, helped out and mixed the record.

Eminem caught Interscope's attention by finishing second at which 1997 Los Angeles battle contest?

Rap Olympics winner Otherwize beat him in the final, but an Interscope intern in the crowd asked the runner-up for a copy of his EP. It was soon playing in Dr. Dre's hands.

Which Brooklyn rapper teamed up with Mos Def to release a 1998 album as the duo Black Star?

Talib Kweli and his partner took the name from the Black Star Line, a shipping company founded by the Pan-Africanist Marcus Garvey.

Which Atlanta group's 1995 debut album, Soul Food, popularised the phrase 'Dirty South'?

Goodie Mob counted CeeLo Green among its four members before he left for a solo career. The phrase itself was originated by the rapper Cool Breeze.

Which Brooklyn-raised rapper's 1993 single 'Ruffneck' made her the first solo woman in rap with a gold record?

MC Lyte had already become the first female rapper to release a full solo album, with 1988's Lyte as a Rock. The gold single also earned her a Grammy nomination.

Which trio marked the end of its 'D.A.I.S.Y. Age' with a 1991 album cover showing a broken pot of daisies?

De La Soul wanted distance from the hippie image of the debut album 3 Feet High and Rising. A video from the new record even shows a pot of daisies being smashed.

MTV once filmed Ol' Dirty Bastard riding a limousine to pick up which benefit while his album sat in the top ten?

Food stamps and a $375 welfare cheque were still his on paper, because he had not yet filed that year's taxes. His caseworker cut him off after seeing the segment.

Which Junior M.A.F.I.A. rapper followed the group's success with the 1996 solo debut Hard Core?

Lil' Kim made the album with the Notorious B.I.G. as executive producer, and he performs on four of its songs. It entered the Billboard 200 at number 11.

Which Philadelphia rapper, billed as the Ruff Ryders' first lady, topped the Billboard 200 with her 1999 debut?

Eve was only the third female rapper to top the album chart, after Lauryn Hill and Foxy Brown. She grew up in West Philadelphia and later moved to Germantown.

In Ice Cube's 'It Was a Good Day', the narrator's ideal day includes the Lakers beating which team?

The SuperSonics result is one of the clues a comedian used in 2012 to work out that the day in the song was probably January 20, 1992.

In his self-mocking 1995 hit 'I Wish', Skee-Lo blames his love life on not starring in which sport?

Basketball stardom tops his wish list, along with being much taller. The verses also mention the Los Angeles neighbourhood of Crenshaw, whose street sign turns up in the video.

Which 1992 number one rap single opens with two valley girls gossiping about another woman's figure?

Baby Got Back spent five weeks on top of the Hot 100 even though MTV briefly banned its video. It went on to win the 1993 Grammy for Best Rap Solo Performance.

LL Cool J's 1990 comeback anthem 'Mama Said Knock You Out' grew out of a pep talk from which relative?

His grandmother told him to knock out his critics when he feared he could not survive the rise of gangsta rap. She appears in the closing scene of the music video.

Public Enemy's 'By the Time I Get to Arizona' attacks that state for refusing to observe which holiday?

MLK Day had been cancelled in Arizona by Governor Evan Mecham. The song's video opens with a politician telling the press that the holiday will never be observed in the state.

Which Los Angeles group's 1993 single 'Passin' Me By' has each of its four rappers recount a schoolboy crush?

The Pharcyde formed in South Central Los Angeles in 1991, a playful contrast to the gangsta rap that typified the city. All four romances in the song end in heartbreak.

Nas raps the 1996 album track 'I Gave You Power' entirely from the point of view of which object?

A gun narrates the whole song in the first person. Nas said he was around a lot of firearms at the time he wrote it and decided to rap about them.

Lauryn Hill's 'To Zion', featuring guitarist Carlos Santana, is a tribute to which person in her life?

Her son Zion was born in 1997, and the lyrics describe her decision to have him rather than put her rising career first.

Salt-N-Pepa re-recorded their 1991 hit 'Let's Talk About Sex' with new lyrics addressing which health crisis?

AIDS was the focus of the alternate version, sent to radio as a promotional single. The original was already hailed as one of the most uncompromising safe-sex raps ever written.

In Warren G and Nate Dogg's 1994 hit 'Regulate', the narrator is robbed after trying to join which game?

Dice players hold Warren G up as he cruises Long Beach alone at night. The pair said the hold-up was a real incident that happened to a friend of theirs.