Robert De Niro is Paul Vitti, the most powerful New York gangster. He's as tough as they come, until lately. He's having problems controlling his emotions. The only way he can solve his problem is talk with a shrink (Billy Crystal), but he must do it secretly or the other mob gangs might find out and "whack" him.

De Niro and Crystal together on screen is such an odd pair that's it's very entertaining. Crystal provides the shtick, but it's De Niro's comic performance that makes the film a winner. His sobbing will bring on the chuckles. It looks as though he's really enjoying playing this character, because it allows him to poke fun at himself. Most people regard De Niro as "that mob guy" or "the guy who is in every mob movie". This time, he gets to show us the softer gangster.

Lisa Kudrow plays Lisa Kudrow. Sure, she is Crystal's fiancee in the movie, but having only about 15 minutes of screen time, who cares. Ramis should have cut her from the movie because all of her scenes just take away from what De Niro and Crystal are doing. Joe Viterelli is De Niro's mug, or goon, whatever you want to call him. He's sent to get Crystal everytime the boss wants to talk, no matter where Crystal is at or what he's doing. He's amusing in the dumb gangster role.