When mobster Paul Vitti (Robert De Niro) suffers a crisis of confidence, threatening his ability to lead his criminal empire, he turns to professional help in the way of Dr. Ben Sobel (Billy Crystal) a psychiatrist who accidentally became acquainted with two of Vitti's henchmen. Dr. Sobel and his finance, (Lisa Kudrow) soon have their world turned upside down by Vitti's increasing demands for Sobels services which displace any semblance of order for the good doctor's heretofore mundane existence. Meanwhile, the growing importance of "the shrink" to the operation of the Vitti organization has not gone unnoticed in the law enforcement community, and the FBI approaches Sobel with an offer he cant refuse: betray Vitti by wearing a wire or spend a long time in a federal prison.
Complications escalate, and Ben finds himself dodging bullets, federal agents and rival gang members, but still wanting to fulfill his professional obligation to help the conflicted mob boss. It all comes to a climax when Sobel must act as Vitti's consigliore at a sit-down of the major crime syndicates to represent the famiglia and confront rival gang chieftain, Primo Sidone (Chazz Palminteri).
Complications escalate, and Ben finds himself dodging bullets, federal agents and rival gang members, but still wanting to fulfill his professional obligation to help the conflicted mob boss. It all comes to a climax when Sobel must act as Vitti's consigliore at a sit-down of the major crime syndicates to represent the famiglia and confront rival gang chieftain, Primo Sidone (Chazz Palminteri).