Bottle Rocket (1996)

"They're not really criminals, but everyone's got to have a dream."

Upon his release from a mental hospital following a nervous breakdown, the directionless Anthony joins his friend Dignan, who seems far less sane than the former. Dignan has hatched a harebrained scheme for an as-yet-unspecified crime spree that somehow involves his former boss, the (supposedly) legendary Mr. Henry.