Several years after mob boss Paul Vitti (ROBERT DE NIRO) came to him with anxiety problems, psychotherapist Ben Sobel (BILLY CRYSTAL) suddenly finds the mobster back in his life. During his father's funeral, Ben receives a call from Paul who believes his life is in danger. When Ben hangs up on him, Paul apparently cracks and begins alternating between bouts of catatonia and apparently believing that he's part of "West Side Story," complete with singing.
Since Ben earlier treated him, he's called in once again to examine Paul and determines that the stress of prison life may have brought on this mental deterioration. Accordingly, Justice Department official Richard Chapin (JOHN FINN) assigns Ben as Paul's temporary custodian and releases the mobster from prison.
Ben is given a month to get Paul back into mental competency and find him a job, but the moment they're beyond the prison gates, Paul snaps back into his normal self. Even so, Ben insists that he must stay at his house, much to the chagrin of his wife Laura (LISA KUDROW) and amusement of his son Michael (KYLE SABIHY).
Despite that and having agents Miller (JAMES BIBERI) and Cerrone (CALLIE THORNE) following his moves, Paul, with the help of his bodyguard, Jelly (JOE VITERELLI), sets out to discover who wants him killed.
Perhaps it's his mob family's tough new boss, Patti LoPresti (CATHY MORIARTY-GENTILE), or her intimidating lieutenant, Eddie DeVol (RAYMOND FRANZA), or maybe rival mob boss Lou "The Wrench" Rigazzi (FRANK GIO) wants him out of the picture.
At the same time, Paul tries to hold down a variety of jobs to meet his parole conditions. He eventually finds himself on the set of "Little Caesar," a TV mob drama, working for director Raoul Berman (REG ROGERS) and coaching Australian actor Anthony Bella (ANTHONY LAPAGLIA) in the ways of being a mob boss.
As the attempts on his life continues, Paul tries to figure out who's responsible, all while plotting his next big heist, all of which nearly drive Ben to the point of a breakdown.