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Rushmore (Wes Anderson, USA, 1998)

The hint of genuine pathos [Murray] brings to Rushmore tempers Schwartzman’s brash, sometimes off-putting antics, gracing an already great comedy with surprising depth and heart.
— Scott Tobias, AV Club

Wes Anderson's breakthrough movie stars Jason Schwartzman as Max, the smart-ass king of extracurricular activities at the prestigious Rushmore Academy. He finds two unlikely soulmates in Bill Murray's industrial magnate and Olivia Williams' first-grade teacher, but a budding romance between the two adults threatens Max's own designs on the lovely schoolteacher.