Is this a coming of age story of a fifteen-year-old geek of everything except academics? Perhaps on the surface it is, or maybe you'd be laughing too hard to care--but I don't see it simply as the trials and tribulations of a teenager with plenty of gags thrown in. Rushmore is about the confusion of different types of love.
Max Fischer (Jason Schwartzman) is that fifteen-year-old geek who attends Rushmore, an elite prep school for the children of the rich. Max's father, however, is simply a barber and Max was only accepted into Rushmore on an academic scholarship due to his playwriting skills in second grade. Max still loves to put on plays, but his obsession with extracurricular activities are tempered with his dismal grades in academics.
Max has a strange relationship with Herman Blume (Bill Murray) a millionaire and father to twins who go to Rushmore. The seemingly odd pairing works because both of these characters are exact mirrors to each other--both used to getting their own way. Things get complicated when Max tracks down the writer of a Jacques Cousteau quote in a textbook--Rosemary Cross (Olivia Williams) who is a first grade teacher--and both Max and Blume promptly become infatuated with her.
The confusion comes in when Max mistakes loving a person with loving a thing (such as extracurricular activities and playwriting) and begins to pursue Ms. Cross with the single-mindedness that strays dangerously into stalkerdom. When Ms. Cross rejects him because, after all, he is only fifteen, Max interprets this as a rejection from everything and attempts to self-destruct by becoming a dull nobody.
Of course, things do end happily, but one must wonder if Max really did learn how to compromise or not--the public school he ends up at allowed him to put on a play with fires and explosives on stage.