Shaun Brumder, played by Colin Hanks, becomes obsessed with becoming a writer after reading a book by Marcus Skinner, a Stanford professor. He realizes that he needs to attend Stanford to achieve his dream. Shaun's grades are not great, but he convinces his English teacher, Mr. Burke (Kevin Kline), to write him a stellar letter of recommendation.
However, when Shaun's application is rejected, he finds out that his guidance counselor, Ms. Cobb (Lily Tomlin), sent the wrong transcript to Stanford. Shaun and his girlfriend, Ashley (Schuyler Fisk), set out to appeal the decision and try to get Shaun's application re-considered.
Along the way, Shaun faces many obstacles, such as his dysfunctional family, including his drug-addicted brother, Lance (Jack Black), and his mother, Cindy (Catherine O'Hara), who is more concerned with her own priorities than Shaun's dreams.
Shaun's determination leads him to meet with Marcus Skinner (played by Kevin Kline in a dual role), who helps him see the value in writing about his own life experiences. Finally, Shaun is given a second chance to apply to Stanford and, with the support of his newfound mentor, achieves his dream of being accepted into the university.
