Rushmore (1998)

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Wes Anderson directs this acclaimed comedy starring Jason Schwartzman as Max Fischer, a tenth grade pupil at Rushmore Academy. When not daydreaming, Max pours all of his energy into his beloved extra-curricular activities, often to the neglect of his studies. His determination to make a name for himself is sent into overdrive by the arrival of pretty new teacher Miss Cross (Olivia Williams). Outside of school, Max is taken under the wing of middle-aged steel tycoon Herman Blume (Bill Murray), but things begin to go awry when Blume falls for Miss Cross himself and Max becomes unhinged with jealousy. His schemes to win the affections of his teacher grow ever more extreme, while his academic life threatens to collapse around him.