| Director | James Signorelli |
|---|---|
| Box office | $29.3 million |
Montgomery "Monty" Capuletti is a hard-living, heavy-drinking, pot-smoking, gambling family man who makes his living as a baby photographer in New Dorp, Staten Island. He loves his wife Rose but has a very tense relationship with his wealthy, snobbish mother-in-law, Kathleen Monahan, who runs a successful department store chain and hates the way Monty acts and lives. There is an added ethnic rivalry between Monty and his wife's family, as he is Italian and they are Irish.
The irresponsible Monty cannot even pick up a wedding cake for his engaged daughter Allison without fouling up. He and his best friend Nicholas "Nicky" Cerone are smoking marijuana while driving, and an accident destroys the cake. Allison's wedding to Julio goes off without a hitch, at least until the wedding night, where Allison, a virgin, is uncomfortable about having sex, frustrating Julio. Julio makes routine unsuccessful dramatic efforts to win her over, unsuccessfully.
After Kathleen dies in a plane crash unexpectedly, his family is in for an inheritance. Attorney Daniel Scrappleton reveals that Kathleen left a stipulation in her will that if Monty is able to curb his vices for a year by going on a diet and giving up drugs and gambling, he will receive $10 million. If not, the family gets nothing and it will go to her nephew Clive Barlow. Monty's gambling and drinking buddies are also interested in whether or not Monty can really give up everything and bet whether or not he will make it. Despite this, Nicky is supportive and helps Monty during this time.
Monty and Nicky go to the mother-in-law's department store and find awkward fashions, catering to a clientele which clearly does not include the likes of Nicky and Monty. Nicky argues that it may not be worth it to Monty if this is the kind of atmosphere he will be exposed to, but Monty points out he must tough it out to provide for his wife and daughters, not just him. Meanwhile, Clive does his best to undermine Monty's resolve so the money and department store can instead be left to him. Clive sets up a clothing line designed to humiliate Monty, but even this is unsuccessful.
Monty ultimately reforms following four weeks in the hospital after accidentally being shot in the butt by Julio trying to prove himself. When the entire year is up, he, his family, and some of his friends celebrate aboard a boat. To his chagrin though, Kathleen turns up. She had faked her own death simply to persuade her slovenly son-in-law to straighten up. In addition, Clive was told by Scrappleton that he was also tested as Kathleen tells Clive that he failed. Ultimately though, she gives the money to Monty on the basis he upheld her stipulation.
Now rich, Monty and his family live in a mansion. Still in control, Kathleen denies Monty dessert and coffee then commands her butler to have a beer she found in the refrigerator be thrown out. Monty gleefully agrees to each action then says he is heading out for a walk while having the butler throw out the glazed fruit as well. Kathleen gloats about her actions and that she finally has Monty under control to her daughter's chagrin. Unbeknownst to Kathleen, Monty has actually proceeded to a hideaway under the house to join Nicky and his friends for pizza, poker, and beer while talking about his evening with the family.