Rushmore

The film that launched the careers of both Wes Anderson and Jason Schwartzman, 'Rushmore' is a sharp, funny, and surprisingly poignant look at an eccentric high school student. Max Fischer's obsession with his school and his complicated friendship with a wealthy industrialist creates a unique dynamic that is both hilarious and uncomfortable. It established many of the tropes that would define Anderson's career, including the use of specific music, quirky characters, and a distinct visual style. It remains a cult classic for its raw energy and brilliant script.