“Why you always so mad?” Tupac’s Lucky asks Janet Jackson’s Justice during his first appearance in John Singleton’s Poetic Justice. “You must ain’t got no man 'cause you don’t never smile.” Only Tupac Shakur could (passively) tell a woman she should smile more and make it somewhat redeemable.

At the core of Poetic Justice are the interactions between emotionally adrift 20-somethings. Jackson is the movie's lead, but Tupac is its heart. As Lucky, he’s charming and repugnant; volatile and vulnerable. His performance reflects the same dissonant, yet sincere range of emotions heard on "Keep Ya Head Up" and "Holler If Ya Hear Me" from his Strictly 4 My N****Z album, released five months before the film. This restlessness marked Tupac's scenes with Jackson, as well as his archetypal Gemini existence off-camera. —Julian Kimble