Orange County
Shaun Brumder (Colin Hanks) is a teenager from affluent Orange County, California. Although bright and intelligent, he has very little interest in education or studying, instead trying to lead a carefree SoCal lifestyle of surfing, drinking, and partying. A turning point comes when Shaun's best friend Lonny (Bret Harrison) is killed in a surfing accident, causing Shaun to rethink his own life. One day, he finds a novel on the beach by the author Marcus Skinner, which quickly inspires him to become a writer. Upon learning that Skinner is an English professor at Stanford University, Shaun makes it his goal to attend Stanford and study under him, seeing it as an opportunity to escape from his superficial life in Orange County.
Shaun dramatically improves himself academically, obtaining high grades and SAT scores as well as becoming the president of his graduating class. Following the advice of his guidance counselor, Ms. Cobb (Lily Tomlin), who tells him that he is a "shoo-in" for acceptance, Shaun applies only to Stanford. This severely backfires as Shaun later finds out that he is rejected from Stanford, ironically because Ms. Cobb mixed up his academic transcript with that of a much less intelligent student. Shaun then reaches out to his wealthy father Bud (John Lithgow), who had left his wife and family to marry a much younger woman (Leslie Mann), pleading him to donate money to Stanford in order to increase his chances of being accepted. Bud, however, disapproves of Shaun's dream of being a writer and refuses. In an attempt to help him, Shaun's animal rights activist girlfriend Ashley (Schuyler Fisk) successfully convinces her friend Tanya (Carly Pope) to allow Shaun to be interviewed at his home by Tanya's grandfather, a Stanford board member, so Shaun can explain his situation. Unfortunately, the antics displayed during the interview by his dysfunctional family members, including his alcoholic, emotionally fragile mother Cindy (Catherine O'Hara) and his dim-witted stoner brother Lance (Jack Black), cause Shaun's interviewers to storm out in anger and disgust.
In a last-ditch effort to get him accepted, Ashley and Lance convince Shaun to drive to Palo Alto and plead his case directly to Stanford Admissions Director Don Durkett (Harold Ramis). By the time the trio arrive on campus, it is nighttime and the admissions building is already closed. While Lance distracts (and seduces) the secretary on duty in the office, Shaun and Ashley steal the address to Durkett's house. They arrive at his home, where Shaun shows him his real high school transcript. Although impressed with Shaun's credentials, Durkett is reluctant to admit him, as it is already very late in the admissions process. After much groveling, Shaun finally convinces Durkett to go back to his office in the Admissions Building and give it a second thought. Disaster strikes again, however, when Ashley drugs Durkett by accident with Lance's ecstasy, stored in an Excedrin bottle, thereby causing Durkett to become high. Things go from bad to worse when Shaun and Ashley arrive at the Admissions Building and find it engulfed in flames, caused by Lance starting a fire while he was seducing the receptionist to distract her; Lance is now wanted for arson. They abandon the hallucinating Durkett and flee the scene to avoid being arrested.
Ashley finally becomes frustrated with Shaun's obsession of only getting into Stanford, and points out that his attending would mean they would be separated, thus ending their relationship. She then angrily leaves Shaun on his own. Depressed, Shaun wanders the campus and meets a female student who invites him to a frat party. There, he witnesses the behavior of the Stanford coeds and is disappointed to learn that they are just as vapid and ditzy as the girls he knew from Orange County. After leaving the party with a more cynical view of college, Shaun, by chance, runs into Professor Skinner (Kevin Kline) and is invited to his office to chat. Skinner is amused with Shaun's belief that he must study and work in a highly intelligent environment in order to become successful, pointing out that many famous authors such as James Joyce and William Faulkner grew up in places that were not intellectually stimulating, but still became great writers. Having an epiphany, Shaun realizes his previous misguided intentions and seeks out Ashley to apologize to her. After catching up with her, the two also pick up Lance (who is still hiding from the police) and drive home.
Back in Orange County, Shaun's parents seek out each other to determine how to deal with Shaun's problem. They end up reconciling, realizing that they are much happier together than with their respective new spouses. They also conclude that they have not been very good parents to Shaun and, in an attempt to make amends, Bud donates enough money to Stanford for the construction of a brand new Admissions Building (ironically, to replace the one that Lance burned down). This action gets Shaun accepted into Stanford. Although Shaun is initially ecstatic, he then remembers the things that both Ashley and Professor Skinner had told him. Shaun finally decides to stay in Orange County with Ashley and his family because he loves them too much to leave them, and he is now able to view living in Orange County as a positive influence for his writing career, rather than a detriment. The film ends with Shaun going surfing with his friends again for the first time since Lonny's death.
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