Lauryn Hill's Miseducation of Lauryn Hill was the first hip hop album to win the Grammy for Album of the Year in 1998 — and went on to sell 19 million copies worldwide. This quiz covers 50 questions on the golden era that gave us Biggie, Tupac, Wu-Tang, and the rivalry that changed music forever.
You'll explore the East Coast/West Coast rivalry and its tragic consequences, the albums that defined a generation from Illmatic to The Chronic, the rise of Southern hip hop through OutKast and Master P, the women who broke barriers from Missy Elliott to Lil' Kim, and the labels that built empires.
While deeply subjective, Nas's Illmatic (1994) is most frequently cited by critics and fans as the greatest hip hop album of all time. Other strong contenders include The Notorious B.I.G.'s Ready to Die, Wu-Tang's Enter the Wu-Tang (36 Chambers), and Lauryn Hill's Miseducation.
The rivalry escalated from competitive regional pride into personal animosity, fueled by the shooting of Tupac at Quad Studios in 1994 (which he blamed on Biggie and Puffy), Suge Knight's provocative comments at the 1995 Source Awards, and diss tracks. It ended tragically with both Tupac and Biggie murdered within six months.
Tupac Shakur is the best-selling rapper of the 1990s, with over 75 million records sold worldwide. His prolific recording pace — he recorded hundreds of songs, many released posthumously — contributed to his remarkable sales figures that continue decades after his death.
Last updated: March 2026