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 adores his wife Rose, but his relationship with his wealthy, snobbish mother-in-law, Kathleen Monahan, is perpetually tense. Kathleen runs a successful department store empire and looks down on Monty’s unruly, carefree nature, creating a sharp ethnic and class contrast between Monty’s Italian roots and Kathleen’s Irish heritage. The story frames these tensions against a backdrop of family loyalty, financial stakes, and the pressure to reform.
A wedding serves as a focal point for the mounting chaos. Monty and his best friend Nicky Cerone—a steadying presence who also champions Monty’s better angels—are found smoking marijuana and, in a careless moment, cause an accident that ruins the wedding cake for Monty’s daughter Allison and her fiancé Julio. Despite this hiccup, Allison’s wedding proceeds, but the newlyweds’ intimate life soon encounters awkwardness. Allison, a virgin on her wedding night, feels uneasy about sex, and Julio makes earnest but not always effective attempts to win her over, leaving their early married life in a delicate balance of expectation and unease.
The plot takes a sharp turn when Kathleen dies in a plane crash, leaving a fortune behind—but with a conditioning twist. Attorney Daniel Scrappleton reveals that Kathleen has left a will stipulating that Monty must curb his vices for a full year—abolish drinking, drugs, and gambling—by living a disciplined life. If he meets the challenge, he will receive a $10 million inheritance; if he fails, the entire sum goes to Kathleen’s nephew, Clive Barlow. Monty’s friends, along with Nicky, eagerly weigh in on whether Monty can actually pull this off, turning the wager into a barometer of his resolve.
To prove his seriousness, Monty and Nicky venture into Kathleen’s department store to face an environment that feels exquisitely alien to Monty’s world. They encounter fashions and a consumer culture designed for a clientele far removed from their own. Nicky questions whether the ordeal is worth it if the social atmosphere continually tests Monty, but Monty insists that the challenge is necessary not only for his family’s future but for his own sense of responsibility. Clive, meanwhile, schemes to undercut Monty at every turn, orchestrating a humiliating clothing line to undermine him. Yet Monty’s resolve remains resolute, even as the public spectacle highlights the gulf between Monty’s rough-hewn instincts and Kathleen’s exacting standards.
A turning point comes after a hospital stay that lasts four weeks, during which a gun misfire leaves Monty with a buttock injury—an incident sparked by Julio’s misguided attempt to prove himself. The period of rehabilitation gives Monty time to reflect and gradually rebuild his self-control. When the year is finally up, Monty, his family, and a circle of friends celebrate aboard a boat, hopeful about the future and the new stability in their lives. Yet Kathleen reappears, having faked her own death to test Monty’s commitment. She informs Clive that he, too, has been tested and reveals that he did not pass. The moment seems to settle into a clear verdict: Monty’s steadfastness has earned the reward Kathleen promised.
In the end, the inheritance goes to Monty, and the family ascends into a life of wealth and mansion living. Kathleen maintains a tight grip, even in victory, attempting to control Monty’s daily choices—denying dessert, coffee, and even a beer kept in the refrigerator—while ordering the butler to dispose of items he enjoys. Monty complies outwardly, yet on a covert level he quietly resists. The real twist comes as he slips away to a hidden corner under the house to join Nicky and their friends for pizza, poker, and beer, quietly plotting his next moves and reflecting on the balance between his daytime standards and the life he continues to share with his companions. The film closes on the image of Monty navigating two worlds: the outward, disciplined posture demanded by his new wealth and the unguarded camaraderie that has always sustained him.
