Plot

The story about the relationship between a rebellious 1950s teenager and his abusive stepfather, based on the memoirs of writer and literature Professor Tobias Wolff.

In 1957, a son and mother flee the East and an abusive boyfriend to find a new life, and end up in Seattle, where the mother meets a polite garage mechanic. The boy continually gets into trouble by hanging out with the wrong crowd. The mom marries the mechanic, but they soon find out that he's an abusive and unreasoning alcoholic, and they struggle to maintain hope in an impossible situation as the boy grows up with plans to escape the small town by any means possible. Based on a true story by Tobias Wolff.—Ed Sutton <esutton@mindspring.com>

In October of 1957, Tobias "Toby" Wolff (Leonardo DiCaprio) and his struggling single mother Caroline (Ellen Barkin) are driving from Florida to Utah in search of better luck after Caroline was beat up by her latest boyfriend. Caroline has bought a Geiger counter and intends to get rich on uranium in Salt Lake City even though no uranium has been found there. Toby narrates that his birth father left his mother a long time ago and took Toby's older brother with him. In Salt Lake, Caroline gets a new job and Toby starts a new school. Soon Caroline's ex, Roy (Chris Cooper), turns up after tracking Caroline down. He gives Toby a rifle as a present and tries to reestablish his relationship with Caroline, but when he becomes too controlling for her, Caroline decides to pack up and skip town on a Greyhound.

Six months later in Seattle, Toby is skipping school, calls himself Jack and has Elvis hair. He and his two friends watch Superman on TV and talk about sex. Toby is living in a boarding house with Caroline, who is dating an attractive and well-mannered man, Dwight Hansen (Robert De Niro). He invites Caroline and Toby to stay the weekend at his home in the small town Concrete. They go to a turkey shoot; Dwight had promised Toby a chance to shoot, but it turns out the rules forbid it. Instead, Caroline enters the shoot as the only woman and ends up winning much to Dwight's dismay. Dwight has three children of his own, and he praises Concrete to Caroline hoping to persuade her to stay.

Back in Seattle, Toby is caught carving obscene words into a bathroom wall and is suspended. Desperate and short on cash, Caroline agrees to Dwight's suggestion that Toby should live with him for a while. Dwight picks him up, and on the drive Dwight shows his nasty side for the first time, threatening Toby with what he will do to him if he doesn't behave. He has Toby's hair cut, enrolls him in the boy scouts and gets him a paper route. Caroline and Dwight are married. It turns out there are many things they don't see eye to eye on, starting with their wedding night. Dwight has a volatile short fuse and has zero tolerance for excuses. Toby complains when Dwight keeps the money from Toby's paper route and won't buy him gym shoes, but Caroline doesn't want to get in the middle of their differences. Dwight tells stories of how he used to beat people up, which unsettles the family and teaches Toby to do the same. Toby befriends the townsfolk in Concrete, but also meets Arthur (Jonah Blechman), an outsider who does not like to be called a homo. They both initially get off on the wrong foot and beat each other up, but later they become friends. One night Toby takes Dwight's car out for a drive, and when Dwight finds out he beats Toby. Toby pleads his mother if they could flee again, but Caroline says she can't run anymore and that the best thing is to stay. This forces Toby to endure intensifying torture, torment, and humiliation from his abusive stepfather.

Two years later, in the spring of 1960, Kennedy is running for president, and Caroline wants to work for his campaign, to the displeasure of Dwight, who is as abusive as ever. Toby gets an idea to formulate an escape plan of his own when Dwight's eldest daughter announces that she has graduated from high school and will soon relocate to California, where she will enroll at Stanford. Taking matters into his own hands, Toby wants to apply for prep schools and live with his older brother, Gregory, who lives on the East Coast with their father, but he has sub par grades and enlists Arthur's help him forge his transcript. Arthur (wants to leave because he knows he will never fit in and that there is more to life than living in Concrete) is reluctant to offer his assistance, stating that Toby is behaving more like Dwight, although he eventually helps Toby to falsify his grade records. When schools start to decline his applications, he realizes that he may have to stay in Concrete like his friends and gets a job in a grocery store. But one school accepts his application and sends an interviewer, who Toby successfully convinces of his suitability for higher education. Toby is accepted by The Hill School in Pottstown, Pennsylvania near Philadelphia with a full scholarship. When Dwight learns that Toby has received a scholarship he attacks Toby with a mustard jar, and they end up in a fight only ended by Caroline and a baseball bat. Caroline finally realizes that she doesn't have to put up with Dwight, and she and Toby leave town as Dwight whinges about his misfortune.

At a bus stop, Toby bides farewell to his single mother and they embrace one last time before she leaves on a Greyhound, and he waits for his own bus to depart a few hours later. The epilogue reveals the later fates of the characters, including Dwight living in Concrete until the end of his life, Caroline remarrying happily and Toby being expelled from the prep school, serving in Vietnam and becoming an author.