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Overweight, depressed actor James (Jeff Garlin) does improv at Second City. James lives with his mother (Mina Kolb) and constantly cheats on his diet. His life seems to be in a downward spiral. He quits his acting job on a sleazy prank show, his girlfriend (Rebecca Sage Allen) breaks up with him, and his agent (Richard Kind) dumps him. When he visits his friend's daughter's elementary school for Career Day, he embarrasses himself in front of the attractive teacher (Bonnie Hunt) by rambling inappropriately about his personal problems in front of the kids. He hears about a Chicago-based remake of Paddy Chayefsky's Marty, one of his favorite movies, and the role he seemingly was born to play, but he can't even get an audition. One day, after giving up on Compulsive Eaters Anonymous, he seeks solace in an ice cream parlor, where he meets Beth (Sarah Silverman), who quickly wins his heart by offering him free ice cream, and asking him a sexually provocative question. But his attraction to the sexually aggressive and somewhat demented Beth may bring James more problems than it solves.