Rushmore (1999)

A teenager at Rushmore Academy falls for a much older teacher and befriends a middle-aged industrialist. Later, he finds out that his love interest and his friend are having an affair, which prompts him to begin a vendetta.

Director: Wes Anderson

Cast: Jason Schwartzman, Bill Murray, Olivia Williams, Seymour Cassel, Brian Cox, Mason Gamble, Sara Tanaka, Stephen McCole, Connie Nielsen, Luke Wilson, Dipak Pallana, Andrew Wilson, Marietta Marich, Ronnie McCawley, Keith McCawley, Hae-Joon Lee, Adebayo Asabi, Al Fielder