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After his ultra low-budget, indie caper comedy Bottle Rocket, director Wes Anderson (along with co-writer Owen Wilson) peaked with Rushmore, developing a formula and a brand that he has continued to hammer into the ground, with less and less success. But with Rushmore, the story of an eccentric high school underachiever and his relationship to the people around him, Anderson found the right level of quirk without going over the annoyance line and in the process made one of the best comedies of the '90s, a truly unique and special film.

In the teenage mind of Max Fischer (Jason Schwartzman), he’s a scholastic genius, admired by his classmates at his beloved upscale private school, The Rushmore Academy. But in truth he’s a below average student and not very liked by his peers. Max is a different kind of outcast than we usually find in teenage nerds. Instead of rebelling against the school, his goal is to fit in, but his grandiose ideas and belief in himself makes him stand out. His lower income also keeps him at a distance from his peers. Max’s gentle father (Seymour Cassel) is a low-key barber, but Max claims his old man is a brain surgeon. Also at odds with Max is the school’s headmaster (Brian Cox). Max’s enthusiasm seems to be a constant source of stress for him, including Max’s effort to keep Latin in the school’s curriculum, his ambitious school theater production of Serpico, and his efforts to build an on-campus aquarium in a bid to impress a lovely widowed teacher, Rosemary Cross (Olivia Williams).

The one person Max comes to relate to on his own level is a local business tycoon, Herman Blume (Bill Murray at his funniest and most movingly pathetic). Blume has bratty kids he can’t stand at Max’s school, so in Max he sees some of himself, a self-made underachiever at odds with the upper class. Max relates to adults better and Blume is a man-child. At first the two bond but then become foes, fighting for the attention of Rosemary, topping each other in dirty tricks to sabotage their chances with her. Eventually Max is expelled from Rushmore, puts together a new group of comrades at the public school, and directs a hilariously epic play about the Vietnam war called Heaven And Hell. No matter the school, Max makes the most of his opportunities.

With Rushmore, Schwartzman was a find, playing Max as a cross between The Graduate and Holden Caulfield. Though there is a certain charm to Max, director Anderson and Schwartzman manage to walk a thin line perfectly, keeping Max appealing but then letting him show his immaturity. Though he tries to sound like an adult, he still makes mistakes and does childish things. Unlike, say, Juno, this is a kid role written by clever adults, but the dialogue coming out of the mouth of a kid is fully believable. Forgetting his Coppola family connection (he’s Francis Ford’s nephew), it’s no wonder Schwartzman has become a go-to indie character actor, shining in challenging films like Marie Antoinette (directed by his cousin Sophia).

In retrospect Bill Murray has become one of the most interesting actors of the last couple decades. Coming out of TV’s original Saturday Night Live (joining the cast in the third season) he was a giant comedy star in films like Stripes and Ghostbusters. But starting with Tootsie in 1981 he has usually been most interesting as a supporting actor with a strong string of great performances in films as diverse as Ed Wood, Wild Things, Kingpin, and as Polonius against Ethan Hawke’s mumbly Hamlet. With Rushmore (and then Lost In Transition), Murray went to a new level of acting excellence and earned a new respect as more than just a comic actor. No matter the quality of the film, Murray continues to find new shades to his already established film personality, making him still one of the more entertaining actors and one who never fails to surprise audiences.

Since the critical kudos Rushmore received, director Wes Anderson has become a celebrated auteur, but he seems to still be coasting off the style he found with Rushmore: quirky characters in search of family units; beautifully shot, creative sets; while moving '60s pop music plays. By the end of the film, as Max grows and acknowledges his faults, the pathos are earned. When he finally reconciles with Blume and Rosemary, it’s not a teary-eyed moment, but a sweet moment. Anderson’s follow-up, The Royal Tenenbaums, was another exercise in eccentric quirk; a creative hand and a great cast helped it. Unfortunately he continued to push the limits of unearned pathos: The Life Aquatic With Steve Zissou was an unfunny and uncertain wreck in search of a point and then worse, The Darjeeling Limited treated its shallow characters as if they were speaking from the Torah. Just because a guy cries in front of mirror to a cool song by the Kinks doesn’t guarantee that the audience will feel something; in that case all I felt was, "Get me away from these jerks." But with Rushmore they may be jerks, but they are still likable and completely original. In Rushmore the comedy and the pathos blend perfectly (unlike the often forced humanity that Judd Apatow tries to squeeze out of his characters). The film established Schwartzman and Anderson as interesting talents, and, most importantly, it reestablished Murray as one of the moist unique talents of his or any other generation.