In December 2002, in the small fictional town of Dukesberry, New Hampshire, Davey Stone is a 33-year-old Jewish alcoholic troublemaker with a long criminal record whose antics have long earned him the community’s animosity. Davey is arrested for refusing to pay his bill at Mr. Chang’s Chinese restaurant, attempting to evade arrest (“Davey’s Song”), stealing a snowmobile, and destroying festive ice sculptures in the process. At Davey’s trial, Whitey Duvall, a 69-year-old volunteer referee from Davey’s former basketball league, intervenes. At Whitey’s suggestion, the judge sentences Davey to community service as a referee-in-training for Whitey’s Youth Basketball League. Under the terms of the community service, if Davey commits a crime before his sentence is completed, he will serve 10 years in prison.
The next day, Davey’s first game ends in disaster. As Davey causes disruptions and continuously torments an obese player, Whitey then suffers a grand mal seizure, and the game is abruptly halted, Davey forfeiting it to the opposing team for the sole purpose of making said obese player cry. Attempting to calm Davey down, Whitey takes him to the mall, where they meet Davey’s childhood friend Jennifer Friedman and her son Benjamin: Jennifer is now a divorced, single mother having moved back to her hometown and taking a job at the mall after her former husband had left her for another woman that he met online. Whitey reminds Davey that he lost his chance with Jennifer 20 years earlier, but Davey secretly still has feelings for her.
As time progresses, Davey and Whitey’s relationship becomes more strained, especially after Whitey threatens Davey that he will notify the judge when Davey shoplifts a peanut brittle; despite letting him off the hook, Whitey keeps to his word and vows to tell the judge if Davey commits another crime. Whitey’s various attempts to encourage Davey are met with humiliation and assault—including Davey knocking Whitey into a porta-potty. Later, Davey bonds with Benjamin while playing basketball at the community center with two other men; but then the game stops when Davey lets Benjamin cuss at the guys who had lost to them, leading Jennifer to reprimand Benjamin for swearing and scolds Davey for his actions telling him that she doesn’t need her son ending up like him. While the two are driving to their respective homes, they sing about their happy childhood together and how much things have changed (“Long Ago”).
When Davey gets home, his trailer is being burned down by one of the men who lost the basketball match to him. Davey runs into the burning trailer to rescue a Hanukkah card from his late parents, then watches the trailer burn down. Whitey opens his home to Davey, who reluctantly accepts; also living there is Whitey’s diabetic twin sister Eleanore; to keep Davey in line, Whitey and Eleanore explain the complex rules of the Duvall household, stating that Davey will have to leave if he does not abide them (“Technical Foul”). Davey seemingly overcomes them and starts to turn his life around. But Davey’s progress in reforming stops short when Whitey recalls what happened in 1982 twenty years ago: En route to one of Davey’s basketball games, his parents were tragically killed in a car accident, and Davey learned of their deaths when the police showed up after the basketball game. Devastated by the loss of his loving parents and leaping from foster home to foster home, Davey spent the next 20 years numbing his pain with alcohol and petty crime and as a result he ostracized himself away from Jennifer and his other friends. Uncomfortable with this reminder of his tragic, painful childhood, Davey loses his temper and insults both Whitey and Eleanore which results in Whitey kicking Davey out of his home, much to his relief.
Davey spends the rest of the day binge drinking, and that night, he breaks into the closed mall. In his drunken stupor, he imagines the logos of various stores coming to life and confronting him about his inability to grieve for his parents, which they identify as the source of his alcoholism (“Intervention Song”). He finally opens his parents’ Hanukkah card, which contains a heartfelt message praising him for being a good son and asking him to never change the way he is. Davey finally cries and comes to terms with his loss. Just then, two cops arrive to arrest him, but he escapes and boards a bus to New York City. The bus is then forced to stop when a single thumbtack in the road punctures all eight rear tires. Reminded of the Miracle of Hanukkah, Davey walks off the bus, intending to find Whitey and make amends with him.
Davey finds Whitey at the All-Star Banquet, an annual town celebration in which one member of the community is recognized for positive contributions to Dukesberry with the “Dukesberry All-Star Patch”, which Whitey has wanted for 35 years. When Whitey is passed over for seemingly the final time with the award being given to the hook-handed Tom Baltezor, he decides to move to Florida and live the rest of his life in anonymity, feeling like he’s no longer wanted. Risking arrest, Davey enters the hall and sings of Whitey’s many selfless contributions to Dukesberry throughout his life, causing the townspeople to realize the error of their ways (“Bum Biddy”). Davey leads them to Whitey, who has gone to the mall with Eleanore to “speak to it” one more time. The townspeople thank Whitey for his service over the years, and the Mayor officially grants him the Patch Award. All 34 previous recipients of the awards give theirs to Whitey.
Davey and Jennifer reconcile and Whitey goes into a seizure, which he calls “the happiest seizure of my life!”