Rushmore

Rushmore (Criterion #65). 1998 Touchstone Pictures.
Starring: Jason Schwartzman, Bill Murray, Olivia Williams, Seymour Cassel, Brian Cox, Mason Gamble, Sara Tanaka, Connie Nielsen, Luke Wilson
Director: Wes Anderson
Buy Rushmore (Criterion Collection) at Amazon. Also available in a non-Criterion edition (bare bones).

Fifteen-year-old Max Fischer (Schwartzman) attends a school called Rushmore Academy on a scholarship, where he gets involved in many extracurricular activities, chairing many clubs and putting on stage plays, but he is still a poor student; poor enough that there is serious talk about expelling him. In between his many activities, Max befriends wealthy industrialist Herman Blume (Murray), who has two spoiled brat he's putting through Rushmore, and he's unhappily married. Max admires Herman's success, and Herman is impressed by Max's attitude.

Rosemary Cross (Williams) is a widowed teacher who starts at the academy after her husband, a former Rushmore student, dies. Max becomes infatuated with her, and starts trying to win her heart. Rosemary finds this cute at first, but his obsession over her starts to alarm her. Blume tries to talk Max out of this, saying Ms. Cross isn't worth the trouble, only to fall for her himself. They begin dating, and Max is unaware of this. He is soon expelled from Rushmore after he attempts to build an aquarium on the school grounds without the school's permission, and finds himself having to enroll in a public school. At Grover Cleveland High, Max finds that his attempts to join or form new extracurricular clubs have mixed results, at first with the support of Blume and Ms. Cross.

Max's friend Dirk informs him about the relationship between Ms. Cross and Blume, meant as payback for a rumor that Max spread about his mother. Max and Herman fall out, and they engage in some acts of revenge on each other, which sees Max getting arrested for cutting Herman's brake lines, and Blume's marriage ending, thanks to Max telling his wife about his affair. Eventually, Max gives up and concedes defeat, since if he did win the feud, Rosemary would still love Blume. He becomes very depressed and stops attending school.

Around Christmas, a chance meeting between Max and Herman, where he learns that Blume and Ms. Cross have split up, which lifts Max's spirits, and he starts applying himself in school. He also befriends Margaret Yang (Tanaka) and casts her in a play. After being denied once more by Ms. Cross, Max vows to win her back for Herman instead. He invites them to a play he wrote, making sure they are seated next to one another. They reconcile, while Max and Margaret become a couple.

Highly, highly, highly recommended movie. Just be sure to buy the Criterion edition.