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Chicago hitman Critical Jim (Tim Allen) has apprehended his latest New York target, Cletis Tout. The only reason Jim has not yet killed him is that he states he is not really Cletis Tout. The only thing in which Jim finds greater satisfaction than getting the job done, is watching classic movies, especially ones with a good story. As such, Jim gives him the opportunity to "pitch" his story to save his life. Saying that his name is Trevor Allen Finch (Christian Slater), he is a career white collar criminal who recently broke out of prison with a friend to help said friend retrieve a cache of diamonds he hid long ago. Beyond Finch assuming Tout's identity to elude the authorities, which got him into this predicament with Jim, he and his friend found that retrieving the diamonds were not going to be as easy as going back to where he had hid them. There was also the added complication of a young woman, Tess Tobias (Portia de Rossi), entering his life, she, who he may have let slip through his fingers, despite being probably the one with whom he was meant to be. Beyond buying or not buying the story, Jim may want to see his version of the classic Hollywood ending in not only writing the final scene to his satisfaction, but doing his part to ensure it comes to fruition.