Rushmore (1998)

Wes Anderson's comedy, co-written with Owen Wilson, is about a 15-year-old scholarship student at a private academy who is flunking his classes while running nearly every club on campus. Jason Schwartzman, in his film debut, makes Max Fischer infuriating and impossible not to root for, and Bill Murray is wonderful as the depressed tycoon who becomes his friend and then his rival for a teacher's affections. This is the pick for adults who like their comedy dry. Murray won the Independent Spirit Award for Best Supporting Male, and his quiet midlife despair is a big part of why the film plays better at 35 than it ever could at 15.