In 1973, nine-year-old JR Maguire and his mother Dorothy move back in with her parents on
Long Island. Abandoned by his deadbeat father Johnny, a radio DJ known as "the Voice", JR grows up with his mother's working-class family. He finds a surrogate father in his uncle Charlie, the owner of a local bar, "The
Dickens". JR often listens to the Voice on the radio, and Johnny calls with plans to take him to a baseball game, but fails to show up and later flees the state. Imparting life lessons to JR, Charlie shares his love of reading and encourages him to become a writer, while Dorothy is determined that her son will have the college education she never had. Though her own well-educated father never made anything of his life, she insists that JR will one day attend
Harvard or
Yale and become a lawyer. Johnny makes a brief visit, beating up Charlie when he heckles him for his absence in JR's life. Confronting a school psychologist for exploiting JR to hit on Dorothy, Charlie is impressed by his nephew's writing. JR's grandfather accompanies him to a father-and-son breakfast, and explains that Dorothy is having her cancerous
thyroid removed. She recovers, and JR's knack for word puzzles earns him a spot in Charlie and his friends' bowling league. As a teenager, JR has an interview at Yale and meets a priest on the train to
New Haven. He is admitted to the university, to his family's delight, and later brings his roommates home to meet Charlie, having their first of-age drinks at The Dickens. JR strikes up a romance with his classmate Sidney, who brings him home to
Westport, Connecticut. After sneaking him up to her room for the night, she reveals that she is seeing someone else, leading to an uncomfortable breakfast with her "lower-upper-middle class" parents before he departs. Continuing his studies, JR encounters the same priest on the train, and is unsuccessful in winning Sidney back. Graduating in 1986, he receives one of his father's sporadic phone calls. JR presents his mother with a class ring, but disappoints her by eschewing law school and moving home to work on his novel. Ignoring his friend Wesley's advice, he continues to pursue Sidney with guidance from Charlie, and is hired as a trainee at
The New York Times. Learning that Sidney has married her college boyfriend, JR is let go from the Times. Charlie is briefly hospitalized, and encourages JR to incorporate his recent setbacks into his novel. On Charlie's advice, JR finds his father in
North Carolina, but realizes that he remains an abusive alcoholic. Johnny assaults his girlfriend and JR has him arrested, finally standing up to his father. Returning home, where his mother has found a new job, JR moves to
Manhattan, but not before Charlie gives him his car. Charlie and his drinking buddies see his nephew off, and JR is determined to prove himself as a writer. During the credits, young JR spends a day at the beach with Charlie and his friends. ==Cast==