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Mob boss Paul Vitti (De Niro) is nearing the end of his term in Sing Sing, and the FBI agents monitoring him are baffled. Day after day they watch as New York's most notorious gangland figure walks around his cell in a semi-catatonic stupor, occasionally breaking into songs from West Side Story.
Is Vitti having a nervous breakdown because of recent threats on his life by a rival Family or is his odd behavior merely a foxy ploy to get him sprung from jail early? The FBI isn't sure and neither is his former psychotherapist Ben Sobel (Crystal), who gets called in to consult on the case.
The last time Sobel treated Vitti he tried to get to the source of his debilitating anxiety attacks, but barely scratched the surface. It will take time to examine the demons still lurking in Vitti's mind and help put him on the straight and narrow -- time that Sobel doesn't want to give. Not to Vitti. Not now.
Truth is, Sobel has problems of his own. His father has just died, plunging him into an identity crisis in both his personal and professional lives. Furthermore, he knows his wife Laura (Kudrow) will be furious if he allows the unpredictable Vitti back into their lives.
But when Vitti is granted a conditional release into Sobel's care and custody, becoming his patient again and -- even worse -- his houseguest, the reluctant psychiatrist finds that he has no choice. In order to get peace back in his life he must help the troubled gangster sort out his psyche, find gainful employment and go straight – which proves easier said than done.
Under Sobel's tutelage, Vitti applies his unique work experience to the job market, with disastrous results. Working in a jewelry store proves too tempting, being a greeter at a fancy restaurant too humiliating, and selling cars seriously tries his patience ("Look at the size of that trunk -- you could put 3 people in there... I mean, suitcases").
The good news is that Vitti finally appears to be sincere about taking the cure, and he assures Sobel that he won't be dragging the both of them into any dangerous underworld schemes like he did last time. And Sobel wants to believe him. But how can he be sure when guys like Lou The Wrench keep showing up?