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60 free Hard Hip Hop trivia questions with answers — music quiz, new questions added Aug 2026.
This is hard hip hop trivia, written for people who know their Marley Marl from their Mr. Magic. There is nothing here about who released The Chronic or which borough hip hop came from. Instead you get the producers (Dilla and Madlib's duo name, Premier's second group, Madlib's alter ego), the labels (who bankrolled Rawkus, how big Tommy Boy's start-up loan was, who co-founded Rap-A-Lot), and the feuds (the B-side that started the Roxanne Wars, the album that ended the Bridge Wars). It also covers firsts and records: the first rapper signed to a major, the first female rapper with a full solo album, the first Hot Rap Singles number one, the sampling lawsuit that changed everything, and the honours later handed to Grandmaster Flash and Cypress Hill. Regional pioneers from Too Short and UGK to the Geto Boys and Bone Thugs get their due too. If you want the standards first, start with our main hip hop trivia quiz. Every answer was checked against the Wikipedia article on the artist, label or record in question, and each explanation adds one more thing worth knowing.
30 of 60 questions with answers and explanations. Play the quiz
Q 01J Dilla's final album, Donuts, was released how long before his death?
Three days
Three days: Donuts came out on 7 February 2006, Dilla's 32nd birthday, and he died on 10 February 2006 from complications of TTP and lupus.
Q 02J Dilla and Madlib recorded the album Champion Sound under what duo name?
Jaylib
Jaylib was the J Dilla–Madlib duo; Champion Sound came out on Stones Throw in 2003, with each producer rapping over the other's beats.
Q 03DJ Premier formed which duo with Royce da 5'9" in 2014?
PRhyme
PRhyme paired DJ Premier with Royce da 5'9"; their self-titled 2014 debut built every beat from composer Adrian Younge's catalogue.
Q 04Producer Pete Rock rose to fame in the early 1990s alongside which rapper, as a duo?
CL Smooth
Pete Rock & CL Smooth was the duo; Rock is also cited alongside Premier, RZA and Q-Tip as a pillar of 90s East Coast production.
Q 05Madlib recorded The Unseen (2000) under which alter ego?
Quasimoto
Quasimoto is Madlib's helium-voiced alter ego; he made The Unseen (2000) by recording his vocals with the tape slowed so they played back high-pitched.
Q 06Rakim's first solo album, released in 1997, was called what?
The 18th Letter
R is the 18th letter of the alphabet; The Master followed in 1999.
Q 07Eric B. & Rakim's 1987 debut Paid in Full was released on which label?
4th & B'way
4th & B'way, Island's urban imprint, issued Paid in Full on 7 July 1987; the album peaked at No. 58 on the Billboard 200.
Q 08Big Daddy Kane's high-school friend who became his DJ was who?
Mister Cee
Kane also co-wrote some of Biz Markie's best-known lyrics after they became friends in 1984.
Q 09Kool G Rap's 1989 debut Road to the Riches paired him with which DJ?
DJ Polo
DJ Polo was Kool G Rap's partner; Road to the Riches (Cold Chillin', 1989), produced by Marley Marl, was the first of three albums billed to Kool G Rap & DJ Polo.
Q 10What does the name KRS-One abbreviate?
Knowledge Reigns Supreme Over Nearly Everyone
KRS-One stands for Knowledge Reigns Supreme Over Nearly Everyone; Lawrence 'Kris' Parker used it as a graffiti tag before forming Boogie Down Productions in 1986.
Q 11Boogie Down Productions' name comes from a nickname for what?
The South Bronx
'Boogie Down' is a nickname for the Bronx; the South Bronx crew of KRS-One and Scott La Rock put the anthem 'South Bronx' on its 1987 debut Criminal Minded.
Q 12Slick Rick signed with which label in 1986?
Def Jam
Def Jam signed Slick Rick in 1986; The Great Adventures of Slick Rick (1988), featuring 'Children's Story', was his debut for the label.
Q 13EPMD's 1988 debut album was titled what?
Strictly Business
Strictly Business (1988) was EPMD's debut on Fresh/Sleeping Bag Records; its title track rides a sample of Eric Clapton's cover of 'I Shot the Sheriff'.
Q 21Too Short's 1987 album Born to Mack sold an estimated 50,000 copies how?
From the trunk of his car
Too Short sold Born to Mack from the trunk of his car around Oakland, moving an estimated 50,000 copies on his own Dangerous Music label before Jive reissued it in 1988.
Q 22E-40's breakthrough 2006 single 'Tell Me When to Go' was produced by whom?
Lil Jon
Lil Jon produced it; E-40, the Vallejo rapper, founded Sick Wid It Records and the group the Click.
Q 23Bone Thugs-n-Harmony were formerly known by which name?
B.O.N.E. Enterpri$e
Q 14Which rapper became an unofficial member of the Ultramagnetic MCs in 1989?
Tim Dog
Tim Dog, the Bronx rapper behind 1991's 'Fuck Compton' and Penicillin on Wax, ran with Ultramagnetic as an unofficial member and later formed the duo Ultra with Kool Keith.
Q 15Under what name did MF Doom rap in the trio KMD?
Zev Love X
Zev Love X was Daniel Dumile's KMD alias; his brother and bandmate DJ Subroc died in 1993, and Elektra shelved their second album Black Bastards in 1994.
Q 16Before becoming Mobb Deep, Havoc and Prodigy went by which name in 1990?
Poetical Prophets
The pair met at Manhattan's High School of Art and Design.
Q 17Which Outkast album is the only one to have debuted at number one on the Billboard 200?
Speakerboxxx/The Love Below
Speakerboxxx/The Love Below went Diamond and won the 2004 Grammy for Album of the Year.
Q 18The Geto Boys' 'Mind Playing Tricks on Me' peaked at what position on the Hot 100 in 1991?
23
'Mind Playing Tricks on Me' peaked at No. 23 on the Billboard Hot 100 in 1991, the Geto Boys' biggest pop hit, built on an Isaac Hayes 'Hung Up on My Baby' sample.
Q 19UGK's 1992 debut album on Jive was titled what?
Too Hard to Swallow
Too Hard to Swallow (1992) was UGK's Jive debut; the Port Arthur duo of Pimp C and Bun B followed it with Super Tight (1994) and Ridin' Dirty (1996).
Q 20Three 6 Mafia won the Academy Award for Best Original Song for a track from which film?
Hustle & Flow
Hustle & Flow (2005), with Terrence Howard as an aspiring Memphis rapper, featured 'It's Hard out Here for a Pimp', which won Best Original Song at the 78th Academy Awards in 2006.
B.O.N.E. Enterpri$e was the name on their 1993 Cleveland debut Faces of Death, before Eazy-E signed them to Ruthless Records and they became Bone Thugs-n-Harmony.
Q 24What record did The Miseducation of Lauryn Hill set at the Grammys?
First hip-hop artist to win Album of the Year
Lauryn Hill became the first hip-hop artist to win Album of the Year, for The Miseducation of Lauryn Hill at the 1999 Grammys, where she took five awards from ten nominations.
Q 25The Roxanne Wars began over a B-side by which group?
U.T.F.O.
U.T.F.O.'s 'Roxanne, Roxanne' was the B-side of the flop single 'Hanging Out'; 14-year-old Roxanne Shanté answered it.
Q 26Which 2007 album officially retired the Bridge Wars between KRS-One and Marley Marl?
Hip Hop Lives
Hip Hop Lives (2007), a joint album by KRS-One and Marley Marl, formally closed the two-decade Bridge Wars sparked by MC Shan's 'The Bridge' and BDP's answer 'South Bronx'.
Q 27Kurtis Blow's 1979 deal, the first major-label signing of a rapper, was with which label?
Mercury
Mercury Records signed Kurtis Blow in 1979, the first major-label deal for a rapper; his debut single for them, 'Christmas Rappin'', came out that December.
Q 28Which Kurtis Blow single was the first rap record certified gold?
The Breaks
'The Breaks' (1980) was the first rap single certified gold by the RIAA; Kurtis Blow cut it with a live funk band rather than samples.
Q 29Before founding Sugar Hill Records, Sylvia Robinson had a 1973 solo R&B chart-topper called what?
Pillow Talk
'Pillow Talk' topped the Billboard R&B chart in 1973 and reached No. 3 on the Hot 100; Robinson had first hit in 1957 with Mickey & Sylvia's 'Love Is Strange'.
Q 30Yo! MTV Raps actually began on which channel, a year before its US debut?
MTV Europe
Sophie Bramly created and hosted the European original from October 1987.