Rushmore

Max Fischer (Jason Schwartzmann) is a lackluster student at his elite prep school Rushmore. His sole aim in life seems to be desiring to be a member of every club and organization at school. Drifting from class to class with little motivation for anything else, he meets a beautiful teacher Miss Cross, for whom he falls in love. Unfortunately, he is spurned by her as she has feelings for Max's mentor and friend, the older Herman Blume (Bill Murray). Desperate to win her love, Max Max he seeks to rid Miss Cross of Blume, thereby setting off a series love triangle battles whose ultimate resolution surprises even Max, as his insight into life outside of school shepherds him into the start of adulthood.