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Paul Vitti (Robert DeNiro) is still in prison (since the ending of Analyze This). He escapes an assassination attempt during the middle of the night when a guard pumps some bullets into his bed, but Vitti was actually hiding underneath his bed (The old pillows-shaped as a sleeping person under the covers trick)
Vitti realizes someone ordered a hit on him and calls his former psychiatrist Ben Sobel (Billy Crystal) the next morning in the middle of Ben's father's funeral.
Vitti tells Ben someone is trying to kill him and needs his help getting out. Sobel is understandably not in a position to deal with this right now and hangs up on him.
During lunch in the prison lunch hall, a convict attempts to stab Vitti. Vitti thwarts him and the entire room goes into chaos. Vitti suddenly jumps on top of the tables and begins singing the Jets song from West Side Story. He is then taken away by the guards and put into solitary for psychiatric observation.
Ben is summoned to go to the prison by the FBI, to observe Vitti, who everyone believes has lost his mind from alternatively singing West Side Story and then going into a catonic state, day and night. After doing some tests on Vitti, Sobel declares to the head of the FBI that Vitti had a mental breakdown and should be moved to a psychiatric hospital.
The head of the FBI tells Ben that Vitti needs to be sane for his parole hearing in a month and appoints Ben as his guardian and doctor. Ben is shocked by this and refuses, but is threatened by the FBI guy to do this anyway or they will take his license away. As soon as Ben leaves, the rest of the FBI agents meet and discuss their actual motive, which is letting Vitti back out in the streets in the middle of the current mob war to shake things up, and then cleaning up the mess.
Ben picks up Vitti from prison and as they are driving home, Vitti drops the act and yells at Ben for taking so long getting him out of prison. Ben is angry but not really surprised for being tricked and sets the ground rules with Vitti. Vitti must live with Ben and his family for next 30 days and look for a legitimate job so as to impress the parole board. Vitti reluctantly goes along with it, but has other plans of his own: to find out who ordered a hit on him. Is it one of the fueding mobsters: Patty LoPresti, who now heads Vitti's former gang, or their rival, Lou the Wrench. (He got his name from twisting a guy's head off).
At the same time, Ben is still trying to resolve some personal feelings about his father's death and his wife (Lisa Kudrow, who is barely in the film) is not happy with Paul Vitti living in their house. She is justified later that night when Vitti has a "female companion" over the house for the evening and have loud sex all night and the next morning, in the middle of a large family gathering, Vitti and his female friend have a vulgar argument and then walks through the dining room and flashes everyone while adjusting his robe.
Ben sits down with Vitti to discuss his getting a job. We next see Vitti in various jobs. First as a car salesman, which doesn't go well because Vitti ends up being very belligerent when a couple of customers decide not to buy a car after spending an hour with him. Next we see him working at a jewelry store, but all he could think about is his tempation to rob the store. Lastly, we see him as a maitre'd in a fancy restaurant. He doesn't last long there either because he flips out when a customer orders him around. Vitti finally settles on being a creative consultant on the Little Caesar television program.
Vitti and his devoted and roly-poly sidekick Jelly visit Patty LoPresiti (Cathy Moriaty), the head of Vitti's former gang, who denies knowing anything about the attempted hit on Vitti. She asks Vitti to rejoin the gang and he says no and that he is going legit. As soon as Vitti and Jelly leave, LoPresti sends her goon, Eddie to follow them.
While having dinner with the Sobels and the director of the television show, a thug shoots up the restaurant trying to kill Vitti, but misses him. Vitti and Jelly find him later on and after hanging him off the roof of a buliding, they find out he was sent by Lou the Wrench.
Vitti decides to have his gang hang out with him on the set of Little Caesar to buy some time and think things through. He receives a visit from Patty LoPresti and she correctly guesses that Vitti is up to something, with his crew hanging around the lot. Vitti confesses to her that he is working on something big and she will get a piece of it. Patty then insists that Vitti take her goon Eddie along on the job and Vitti reluctantly says yes. As soon as Patty leaves, Vitti receives another visitor, Lou the Wrench, who lies and says that he knew nothing of the attempted hits and that the thug, now dead, was operating on his own. Lou then asks Vitti to join his gang and help him put an end to the war. Vitti refuses and reiterates that he's gone straight. Lou makes an unveiled threat towards Vitti.
Ben comes home and finds his son dressed up because he is now working for Vitti as his driver. Ben is upset by this and also figures out that Vitti is up to something illegal. Ben learns from his son that Vitti and his gang are meeting in a strip club in Queens tonight.
Vitti and his gang do meet up in a strip club later that night. Ben crashes the meeting with the intention of stopping Vitti from going back to his crooked ways. Too late. The meeting gets underway and Ben is forced to take part in the plan because Eddie and his guys are there and they demand that Ben is either in on this thing or he gets killed right now.
The plan is to rob an armored truck filled with gold. The robbery goes as planned. The truck is hijacked next to an enclosed junkyard. Vitti and the gang shoot gas around the truck, disorienting the armed guards. The armored truck is then hoisted over by crane from the street into the yard. The guards are left outside and try to break through the front gate. The gang quickly opens up the truck and proceed to take out the exactly 50 bars of gold and load it into a transit bus. Ben panics and goes off to the side and gets hysterical. Vitti follows him and tries to calm him down. Ben then has a revelation about his feelings for his father and following into his footsteps as a psychiatrist. He then brings up Vitti's childhood memory of seeing his own father murdered. Both men have a moment and start crying in each other's arms. Jelly walks in and breaks up the tender moment.
The gang finishes loading up the bus and leaves the rest of the gold in the truck.
Before anyone has a chance to leave, Eddie and his goons have their guns pointed at Vitti and his gang. Apparently Eddie has been playing both sides and is really working for Lou the Wrench. Eddie plans to take the gold for himself and kill Vitti. Eddie is about to shoot Vitti, but Ben jumps at him and beats him to a pulp. Vitti's gang overpower the rest of the goons and loads them all into the armored truck and raises it up by crane and leaves them hanging for the cops. The cops outside react to sounds of gunfire from a block away. Turns out that Little Caesar is filming on location right there and they were filming a shootout. While the cops and the director argue, Vitti and his gang use this distraction to drive away in the bus.
We next see Vitti and Jelly meeting Ben along the Hudson River in downtown Manhattan. Acting on an anonymous tip, the Feds find the gold in a van owned by Lou the Wrench and his whole crew is arrested, thus putting an end to the mob war. Ben tells Vitti he did the right thing, but Vitti admits that he will always live a life of crime. They then begin singing "Somewhere", from West Side Story and then part ways.
The end credits are shown with bloopers and outtakes from the film.
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