Henry (Keanu Reeves), a man seemingly without ambition, dreams or purpose, gets a wake-up call early one morning when he becomes an unwitting participant in an ill-conceived bank heist. Taking the fall, Henry goes to jail where he meets the irrepressible Max (Academy Award® nominee James Caan), a con man who’s grown far too comfortable with the familiarity and security of his “idyllic” life behind bars.

Upon his release one year later, Henry finds his purpose. Having done the time, he decides he may as well do the crime. Henry convinces the reluctant Max to file for his long overdue parole so he can help stage a robbery. Their plan is simple: by infiltrating a theatre and its current production of Chekhov’s The Cherry Orchard, the unlikely duo will buy just enough time to dig their way to an adjacent bank vault and drive off with the loot. Unfortunately the plan also requires Henry to take the lead role in the play, where he finds himself slowly falling for Julie (Academy Award® nominee Vera Farmiga), the production’s mercurial leading lady.