Infamous and unpredictable, Jesse James (Brad Pitt), nicknamed the fastest gun in the west, plans his next big heist while he launches pre-emptive strikes against those looking to collect the reward the law has placed on his head. Jesse's newest recruits, Robert (Casey Affleck) and Charley Ford (Sam Rockwell), grow increasingly jealous of the outlaw. When they sense an opportunity to kill Jesse, they gun him down, but their actions backfire when Jesse's fame is elevated to near mythical status.

A comic-book nerd and Elvis fanatic Clarence (Christian Slater) and a prostitute named Alabama (Patricia Arquette) fall in love. Clarence breaks the news to her pimp and ends up killing him. He grabs a suitcase of cocaine on his way out thinking it is Alabama's clothing. The two hit the road for California hoping to sell the cocaine, but the mob is soon after them.