Mobster Paul Vitti is released into Dr. Ben Sobol's care, where only more chaos ensues.
The mafia's Paul Vitti is back in prison and will need some serious counseling when he gets out. Naturally, he returns to his analyst Dr. Ben Sobel for help and finds that Sobel needs some serious help himself as he has inherited the family practice, as well as an excess stock of stress.—Tim Salazar
Feigning mental deficiency to get out of the impenetrable Sing Sing prison, the unrepentant mob boss, Paul Vitti, is now released into the custody of his favourite psychiatrist, Dr Ben Sobel. Still having unresolved issues to deal with, the good doctor reluctantly accepts to pick up where they left off after his idiosyncratic relationship with Paul in Analyze This (1999), forced to make his conflicted patient a proper model citizen. Once more, there is yet another pressing deadline, so that the dangerous don is ready before his parole hearing. Indeed, this is one of the most difficult cases in Dr Sobel's entire career. Can he analyse that?—Nick Riganas
Nicky Caesar (Anthony LaPaglia) kills Ducks (Joey "Coco" Diaz) on suspicion of being a rat within his mafia organization, in the TV show called Little Caesar.
Near the completion of his sentence in Sing Sing, Paul Vitti's (Robert De Niro) life is threatened by assassins and corrupt guards while incarcerated. Paul's friends and protectors inside the prison are transferred before the hits on him are carried out. Paul survives by anticipating the hits and hiding under his bed.Paul starts singing show-tunes from West Side Story to get the attention of Ben Sobel (Billy Crystal), who previously hung up on him while attending his father's funeral. Ben is married to Luara (Lisa Kudrow).
The FBI through Agent Cerrone (Callie Thorne) and Agent Miller (James Biberi) calls in Ben to perform psychiatric tests on Paul to determine if he is feigning insanity. Paul appears to be catatonic at times, and responsive at others.After the tests, it appears Paul's mental state is deteriorating, and the FBI lead Richard Chapin (John Finn) approves Paul's release for one month, into Ben's custody, for further therapy. Ben says that the constant stress of being inside the prison, and the threat of assassination, has led to Paul's temporary state of insanity. Chapin says that Paul appears in front of the parole board in 4 weeks, and there is no chance of him getting better inside the prison. Ben is not OK with the plan and argues for Paul to be sent to a halfway house where he can get the care that he needs.
Chapin gives Ben 30 days to get Paul in shape for the parole hearing, which means sane, sober and gainfully employed. If Paul escapes, Chapin promises to hold Ben responsible and to make him pay for it.As Ben drives Paul from prison, Paul immediately reveals that he was faking.Paul says that he does not know who is behind the assassination attempts. He speculates that the mafia families are not happy about the possibility of him returning to claim his share of the pie.Back at the FBI, Chapin reveals to Cerrone and Miller that he knows that Paul was faking. He says that he released Paul to throw a wild card in the middle of the mafia families feuding against each other to take control of the city.
At the same time, Paul is told by De Facto boss Patti LoPresti (Cathy Moriarty-Gentile) that the Rigazzi family wants him dead. Patti also doesn't trust Paul as she believes that Paul came out from prison to take the "family" away from her. Paul meanwhile suspects Patti of putting the hit on him during his stint at prison. Paul tells Patti that he is not interested in the mafia business and wants to be left alone.
Ben talks Paul into finding a regular job as requested by the FBI. Paul attempts to find a legitimate job (he tries a car dealer, a restaurant, and a jewelry store), but his rude manners and paranoia only complicate things further. This ends up in him getting fired each time.
He eventually finds employment working as a technical advisor on the set of a mafia TV series Little Caesar. Little Caesar is produced by Raoul Berman (Reg Rogers), who meets Paul at dinner along with Ben, who acts as a buffer. But, again, Paul is attacked at the restaurant, and escapes when his bodyguard Jelly manages to shoot back. Paul and Jelly track down the hit-man and find that he was sent by Lou "The Wrench" Rigazzi (Frank Gio).Paul meets the Rigazzis and tells them that he is "out" and seeking a new line of employment. Lou says that he is OK until Paul is thinking about going back to work for Patti.
Meanwhile, Patti kidnaps Ben and says that she wants Paul to back at his previous best as a hardcore mafia enforcer. She doesn't want Paul to be reformed or seeking other forms of employment.
At the sets of Little Caesar, Paul asks Jelly to assemble their old crew, and gradually takes over the entire set. Paul spends time coaching Nicky Caesar on the right mafia pronunciation.Patti visits Paul on the sets and says that she knows Paul is planning something big as he has his entire crew back together. She wants her cut of the action.
Meanwhile, FBI agents inform Ben that Paul has his former crew back together and may be planning something major. This rouses Ben's suspicion, and he visits Paul on the sets. Both get caught up in a car chase with Rigazzi hit-men, which ends up with Paul escaping. The FBI blames Ben and gives him 24 hours to locate Paul.
After locating Paul through Ben's son Michael (Kyle Sabihy), who is now working as Paul's chauffeur, Ben discovers Paul is planning a big, armored car heist with LoPresti as a partner. He attempts to intervene and talk Paul out of it, but Paul proceeds, and Ben is forced to go along as well.
The crew ambushes the armored car with smoke grenades and lift it over a fence in the middle of the confusion. They extract over $22 million of gold bullion, but LoPresti's thugs take over, revealing themselves to actually have been working for Rigazzi.
Ben, in a fit of anger, beats one of them, and Paul's men apprehend the others. They use the gold bullion to frame the Rigazzi family, leaving three Rigazzi goons locked in the armored truck suspended from the crane. This leads to the arrest of the entire Rigazzi family, and in turn, prevents a mob war.
Ben meets with Paul and Jelly (Joe Viterelli) near bridges on the New York waterfront, and they part ways again as friends, singing another West Side Story show-tune together.