Rushmore (1998)

Jason Schwartzman, in his film debut, plays Max Fischer, a 15-year-old scholarship student at a prestigious academy who announces his absurd schemes in the solemn tone of a company chairman. Bill Murray, as a lonely industrialist, answers him with a hangdog stillness that became his signature in the years that followed. Wes Anderson's symmetrical framing does much of the joke work, presenting ridiculous behavior with complete formal seriousness. This is the warmest film here and the easiest way in if subtitles or slow pacing put you off the others.