Rushmore(1998)

Max Fischer is a social outcast at the posh Rushmore private school, which is populated by rich and obnoxious boys. Unsuccessful academically, he makes his mark through instigating dozens of clubs, inventing bizarre schemes, and on one occasion, putting on a harsh David Mamet-like play. He also falls for a much older teacher, Miss Cross, and when his infatuation is not returned, his schemes turn vengeful. He is expelled from school, and when he discovers that one of the parents of an obnoxious pupil is having an affair with Miss Cross, he declares war.