Shaun Brumder (COLIN HANKS) is class president at Vista Del Mar High School in Orange County, California. While at one time he was satisfied surfing with his buddies Chad (RJ KNOLL) and Arlo (KYLE HOWARD), Shaun now wants to be a writer thanks to discovering author Marcus Skinner's (KEVIN KLINE) novel about teenage life, "Straight Jacket."
Accordingly, he wants to attend Stanford where Skinner is a professor, not only to become a writer, but also to escape his family life. His mom, Cindy Beugler (CATHERINE O'HARA) is a depressed alcoholic who forgets to give Bob, her wheelchair-bound husband, his medicine, and doesn't want Shaun to leave home for college. His brother, Lance (JACK BLACK), is always high and/or in a perpetual daze, while their estranged and self-absorbed but wealthy father, Bud (JOHN LITHGOW), isn't happy with Shaun's career choice.
Shaun's only real support comes from his girlfriend, Ashley (SCHUYLER FISK), but she isn't crazy about the idea of them going to different colleges. Nevertheless, Shaun is intent on attending Stanford, but when his admission application is rejected due to a clerical error by Charlotte Cobb (LILY TOMLIN), Vista Del Mar's college counselor, his world is shattered.
From that point on, and with the assistance of Ashley and Lance, Shaun sets out to correct the error. That leads them to meeting various people along the way, including Arthur Gantner (GARRY MARSHALL), Stanford's Chairman of the Board of Trustees, and his wife Vera (DANA IVEY); Dean of Admissions Don Durkett (HAROLD RAMIS); and others, all of whom he tries to convince to admit him to Stanford, all while dealing with his family and friends who inevitably complicate matters.