1. Jeffrey Wright as Jean-Michel Basquiat
Character: Jean-Michel Basquiat
Year Released: 1998
Julian Schnabel really struck the right chord with his love letter to genius street artist and contemporary, Jean-Michel Basquiat. Though the film itself can feel a bit bloated and occasionally even heavy handed, it shines through casting. Jeffrey Wright takes the complexity and intrigue of Basquiat on full force, turning the charm and the anger on in equal measure, challenging the perception of an already challenging artist.