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60 free 90s Hip Hop trivia questions with answers — music quiz, new questions added Aug 2026.
52 free 90s hip hop trivia questions with answers. 90s hip hop trivia questions and answers for the golden-age heads: Tupac and Biggie, Death Row and Bad Boy, Illmatic and 36 Chambers, The Chronic and Doggystyle, OutKast at the Source Awards, the Fugees and Lauryn Hill's Grammys, DMX's two number ones in a year, Missy's trash-bag suit, and the pop crossovers - Hammer, Vanilla Ice, Coolio, Will Smith - that everyone pretends they did not own. This is 90s rap trivia built from the records, the labels, the samples and the feuds, not a list of birthdays. Easy questions any fan of the era will get come first (which city Tupac was shot in, what Snoop's mother called him, which musical Jay-Z borrowed for Hard Knock Life) and the later ones will separate the people who actually read The Source: which producer was not on Illmatic, what clause the Wu-Tang negotiated, who The Firm's fourth member was, whose Grammy speech ODB interrupted. Every answer has been checked against a reference page and carries its source. For rap history beyond the decade, see the main hip hop quiz.
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Q 01Tupac Shakur's debut album 2Pacalypse Now (1991) took its title from which film?
Apocalypse Now
He had debuted months earlier as a dancer and rapper with Digital Underground; his mother Afeni was a Black Panther.
Q 02Tupac's Me Against the World hit number one in March 1995 while he was where?
In prison
He was serving a sentence for sexual abuse; the album made him the first artist to top the Billboard 200 from behind bars.
Q 03All Eyez on Me (1996) holds what distinction in rap history?
Rap's first double album
Suge Knight bailed Tupac out of prison in exchange for three albums on Death Row; this was the first, released in February 1996.
Q 04Under what alias did Tupac release The Don Killuminati: The 7 Day Theory?
Makaveli
The name nodded to Machiavelli, fuelling theories that he had faked his death; the album came out two months after he was shot in Las Vegas.
Q 05Tupac was shot in a drive-by on September 7, 1996, in which city?
Las Vegas
He had just watched a Mike Tyson fight; he died six days later, and the case stayed unsolved for 27 years.
Q 06The Notorious B.I.G. borrowed his alias 'Biggie Smalls' from a character in which 1975 film?
Let's Do It Again
Calvin Lockhart played the gangster; Christopher Wallace was born in Brooklyn in 1972.
Q 07Biggie's breakthrough 1994 single, the one that opens 'It was all a dream', is built on which 1983 track?
Mtume's 'Juicy Fruit'
'Big Poppa' followed to number six and a Grammy nomination; the album is six-times platinum.
Q 08Which R&B singer did Biggie marry in August 1994, weeks before Ready to Die came out?
Faith Evans
She later sang on 'I'll Be Missing You', Puff Daddy's tribute that topped the chart for 11 weeks.
Q 09How long after Biggie's murder in March 1997 was his second album, Life After Death, released?
16 days
It debuted at number one and delivered two posthumous chart-toppers, 'Hypnotize' and 'Mo Money Mo Problems'.
Q 10Which magazine's July 1995 cover declared Biggie 'The King of New York'?
The Source
He was inducted into the Rock and Roll Hall of Fame in 2020, three years after Tupac.
Q 11How old was Nas when Illmatic came out in April 1994?
20
The Source gave it a perfect five mics; the cover shows a seven-year-old Nas over a photo of the Queensbridge projects.
Q 12Which of these producers did NOT work on Illmatic?
Dr. Dre
Large Professor and L.E.S. round out the credits; AZ is the album's only guest rapper, on 'Life's a Bitch'.
Q 13Illmatic was hailed as a classic on release, but when did the RIAA certify a million shipments?
2001
Nas's follow-up It Was Written (1996), largely produced by the Trackmasters, went to number one and remains his best seller.
Enter the Wu-Tang (36 Chambers) takes its title from Enter the Dragon and which other kung fu film?
Q 21Sean Combs founded Bad Boy in 1993 after being fired from which label?
Uptown
The first release was Craig Mack's 'Flava in Ya Ear'; by 1997 the label was worth an estimated $100 million.
Q 22In 1995 Suge Knight invited artists to 'come to Death Row' if tired of their executive producer doing what?
Appearing in all their videos
The dig at Puff Daddy is usually cited as the public start of the East Coast-West Coast war.
Q 23Tupac blamed Biggie and Puffy for the November 1994 shooting at which New York studio?
Quad Studios
He was shot in the lobby while Junior M.A.F.I.A. members were upstairs; 'Hit 'Em Up' followed in 1996.
The 36th Chamber of Shaolin
RZA produced it on a shoestring at Firehouse Studio; the deal famously let each member sign solo contracts elsewhere.
Q 15What unusual clause did the Wu-Tang Clan negotiate with their label in 1993?
Members could sign solo deals with other labels
The result was Method Man on Def Jam, Raekwon on Loud, GZA on Geffen and Ol' Dirty Bastard on Elektra within two years.
Q 16The Chronic's cover pays homage to what?
Zig-Zag rolling papers
The title is slang for high-grade cannabis; the album launched Snoop and defined G-funk with its Parliament-Funkadelic bass.
Q 17How did Snoop Dogg get his nickname?
His mother thought he looked like Snoopy
Born Calvin Broadus in Long Beach in 1971, he was rechristened Snoop Lion by a Rastafarian priest in 2012.
Q 18Snoop Dogg's Doggystyle (1993) sold how many copies in its first week on the way to a number-one debut?
806,000
He was facing a first-degree murder charge at the time; he was acquitted in February 1996.
Q 19Which label did Snoop Dogg move to in March 1998 after leaving Death Row?
No Limit
Master P's New Orleans empire released his next three albums; Snoop bought the Death Row brand itself in 2022.
Q 20Death Row Records was founded in 1991 by Suge Knight, Dr. Dre, Dick Griffey and which N.W.A associate?
The D.O.C.
Interscope put up $10 million in 1992; Dre walked out in March 1996 to start Aftermath as the label imploded.
Q 24Andre 3000's line 'The South got something to say' was a response to what?
Being booed at the 1995 Source Awards
The Atlanta duo's Southernplayalisticadillacmuzik had won Best New Rap Group; ATLiens and Aquemini followed.
Q 25Which civil-rights icon sued OutKast in 1999 over a song title on Aquemini?
Rosa Parks
The case dragged on for six years before settling; the duo went on to win Album of the Year for Speakerboxxx/The Love Below.
Q 26Jay-Z's 1996 debut Reasonable Doubt appeared on which label he co-founded with Damon Dash and Kareem Burke?
Roc-A-Fella
It peaked at only number 23 but featured Biggie on 'Brooklyn's Finest' and Mary J. Blige on 'Can't Knock the Hustle'.
Q 27The Fugees' 'Ready or Not' samples an unlikely artist. Who?
Enya
The Score, with its Roberta Flack cover 'Killing Me Softly', sold about 22 million copies, still the most by any hip hop group.
Q 28The Miseducation of Lauryn Hill (1998) was the first hip hop record to win what?
The Album of the Year Grammy
She took five Grammys that night, then a record for a woman; most of the album was recorded at Bob Marley's Tuff Gong studio in Kingston.
Q 29Which lead single from The Miseducation of Lauryn Hill debuted at number one on the Hot 100?
Doo Wop (That Thing)
The album's first-week sales of 422,000 were a record for a female artist; it remains her only solo studio album.
Q 30Coolio's 1995 smash hit interpolates which Stevie Wonder song?
Pastime Paradise
Wonder refused to allow profanity, so it is one of Coolio's few clean tracks; it was 1995's best-selling US single and soundtracked Dangerous Minds.