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A man who was wrongly accused of bank robbery decides to live up to his criminal record in this romantic crime comedy starring Keanu Reeves, James Caan, and Vera Farmiga. Henry (Reeves) was drifting through life as a toll collector in Buffalo, NY, when one morning he happened across a half-baked bank heist. Unwittingly drawn into the harebrained plan, Henry eventually lands in jail for refusing to identify the robbers, and lands in a cell with amiable con artist Max (Caan), who has grown rather comfortable with life behind bars. According to Max, a man must first have a dream in order to find his purpose, and one year later Henry is a free man with an audacious plan. Since he's already on record as a convicted bank robber, Henry figures he may as well try his hand at the criminal lifestyle. After stumbling across an old underground bootlegger tunnel that connects the bank to an adjacent theater, Henry convinces Max to apply for parole in order to help him execute the perfect robbery. Posing as an actor, Henry lands the lead role in the theater's production of Chekhov's The Cherry Orchard, and begins working with Max to burrow their way into the nearby bank vault. But now the more time Henry spends in the theater, the harder he finds himself falling for his capricious co-star Julie (Farmiga), a development that could very well land them all in jail before the final curtain.