Paul Vitti (Robert De Niro) is one of New York's most powerful gangsters. As he's about to ascend to the leadership of a major crime family, he begins having a series of anxiety attacks. Dr. Ben Sobel (Billy Crystal) is a psychiatrist who accidentally rear-ends the car of Vitti's bodyguard, Jelly (Joe Viterelli), unfortunately exposing a man in the trunk. When Sobel gives Jelly his card, he suddenly becomes the solution to Vitti's problem. Vitti has an important mob summit in two weeks, and he needs to be cured immediately. Sobel wants no part of it, as he's marrying news reporter Laura MacNamara (Lisa Kudrow) in a week, but he's given little choice. Sobel must get to the roots of Vitti's problems with his work and his issues with his parents so that the mob boss may become a "happy, well-adjusted" gangster. Meanwhile, Vitti's rival, Sindrone (Chazz Palminteri), is waiting for a chance to strike.