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Working the night shift as a toll collector on a lonely stretch of highway in Buffalo, New York, Henry (Keanu Reeves) is a man seemingly without ambition, dreams or purpose; sleepwalking his way through life. He gets his wake-up call early one morning when he becomes an unwitting participant in an ill-conceived bank heist. Rather than give up the names of the real culprits, Henry takes the fall and goes to jail. There he meets the irrepressible Max (James Caan), a con man who's grown fat too comfortable with the familiarity and security of his 'idyllic' life behind bars, but who also helps plant an idea in Henry's mind which will change his life forever: for a man to have a purpose, he must first have a dream.
Their plan is simple--by infiltrating the theatre and its current production of Chekhov's The Cherry Orchard, the unlikely duo will buy just enough time to dig their way to the adjacent bank vault and drive off with their loot. Unfortunately that plan also includes Henry taking the lead role in the play, where he finds himself slowly falling for the production's mercurial leading lady Julie (Vera Farmiga).
By turns wry, off-beat and simply hilarious, Henry's Crime is the heart-warming story of a man who finds his purpose in life. And then finds his destiny.