2Pac
“Trapped” (Interscope Records/TNT Recordings/EastWest Records America)

2Pac was still buzzing off his breakout appearance on Digital Underground’s “Same Song” when he released the first single from his debut album. Yet its accompanying visuals were starkly different from DU’s funky comedy: shown in a jail facility, 2Pac rapped into the camera, “You know they got me trapped in this prison of seclusion/Happiness living on the streets is a delusion.” The real-life circumstances were different, too — Pac used the release to announce a lawsuit against the City of Oakland after being attacked by police over a jaywalking charge. It all meant that 2Pac would be a very different artist than the fun-loving Digital Underground crew, even as the Underground Railroad laced him with a beat and Shock G ad-libbed on the chorus, “Uh-uh, they can’t keep the Black man down.”

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