#1. Tupac Shakur (VIBE, 1994)

Issue: February 1994
Art Direction: Richard Baker
Photography: Shawn Mortensen

The world might never truly understand Tupac. What, if any of his persona was an act and what was reality? Was he a calculated genius? Was he crazy? Was he both? We'll never know. But the image of him on this classic VIBE cover captures the dichotomy of his character. Even in an insane asylum he maintains a "don't-give-a-fuck" look on his face. Complex later paid tribute to its legacy by wrapping up Lil Wayne in a similarly straight-jacketed pose in 2007 and asking the same question.