Monty Brogan [Edward Norton] has one day to put his life in order before starting a seven year prison sentence for drug dealing. On this day he tries to set things right with estranged father [Brian Cox] and heads out of town with his friends Jacob [Philip Seymour Hoffman] and Slaughtery [Barry Pepper]. Being in touch with his old friends again makes him reconsider his life choices. Is it too late to change?