Rushmore is 20 years old. Even with a two-decade legacy that reaches into cinema’s hallowed history to map out its future, Wes Anderson’s singular screwball tale of love, betrayal and extracurricular activity still isn’t old enough to drink in its own country.

It’s that post-adolescent, pre-adulthood energy that typifies Rushmore and its inimitable protagonist Max Fischer – Jason Schwartzman’s scrappy upstart half-orphan barber’s son, persistently pushing at the confines set around him by the establishment of his beloved titular private school. Max – not quite grown up, no longer a kid – is caught in that fleeting in-between period, a ferocious time of change that will define him for life. Like any teenager, he’s desperately clinging to a romantic past while trying to carve a unique place for himself in an uncertain future.

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Courtesy of: Buena Vista Pictures

When Rushmore was released in 1998, America was caught in a similar transitionary moment. The year started with the Monica Lewinsky scandal, which would weaken the sturdy pillars of Bill Clinton’s administration. Titanic became the first movie to ever gross $1 billion at the box office. In the San Francisco bay, Larry Page and Sergey Brin founded Google, Inc. The US was in a state of flux, barrelling towards the 21st century without a roadmap – politics, culture and technology all set to transform at once.

By comparison, the second feature by a promising, if meek, indie director co-written with his college pal Owen Wilson is, admittedly, small potatoes. But in 1998, everything was about to change – and Rushmore understood that better than most.

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Courtesy of: Buena Vista Pictures

Battles between old and new, familiar and unfamiliar, rage across the movie’s canvas. Just as Max duels his conflicting natures – his love for the traditions and pageantry of Rushmore Academy colliding with an irrepressible urge to shred the rulebook and flunk his classes – his co-conspirators must face their own internal conflicts, while seeing those anxieties manifest before their eyes.

Bill Murray plays local industrialist Herman Blume – a hollow husk of a former hotshot businessman, worn down by a loveless marriage and his asshole twin sons. Purposeless and adrift, his curiosity is sparked by Max’s peculiarities, and the promise of possible new love draws out a spirit and drive he’d long thought lost.

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Courtesy of: Buena Vista Pictures

Kindergarten teacher Rosemary Cross (Olivia Williams) lives with the ghost of her late adventurer husband Edward Appleby holding her back from a new, full life. When she sees fragments of Edward in Max’s gusto and idiosyncrasies, she rediscovers her own agency and sense of self, moving forward from mourning into exciting, uncharted territory.

But progress hurts, as Anderson and Wilson observe. None of these leaps forward come easily, and damage is done. Both Max and Herman fall for Rosemary, which sees their own friendship devolve into a bitter back-and-forth of spiteful pranks. Rosemary, caught between an upstart schoolboy with a crush and a sad-sack older man with an inferiority complex, is able to shed her own grief only to find herself shouldered with the burdens of men who can’t carry their own.

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Courtesy of: Buena Vista Pictures

This friction is incendiary, and leads to explosive incidents and melancholic realisations. Without a clear view of the path ahead, the characters keep crashing into each other – stumbling in the dark for a sense of direction. It takes a protracted string of painful failures to reach the moment of blissful clarity that closes the film and, when that conclusion comes and is accepted by the cast, it is only because they have made peace with the fact that they probably aren’t heading where they want to go. Things will not be how they expect when they reach their destination, but the changes will be fundamental and, hopefully, for the better.

Max’s journey to true maturity, by reconciling naive, nostalgic daydreaming versus cool-headed realism, is mirrored in the story of Rushmore’s own production. Anderson was desperately struggling to keep to his $10 million budget, much of which had to be spent on legacy star Murray who at this point was accustomed to a healthy paycheque. Perhaps perceiving the significance of what was being made in a moment of clarity, Murray agreed to work to scale. He earned $9,000 for his work, but also wrote the director a $25,000 cheque to cover helicopter rental for a crucial shot (that didn’t even make the final cut).

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Courtesy of: Buena Vista Pictures

Effectively losing money on the venture, Murray’s decision would lead to something of a rebirth – both for himself and American indie cinema at large. Following Rushmore, Murray would move away from the sweary, charming goofballs of his 1980s heyday and age disgracefully into the downbeat, self-aware and thoroughly more nuanced work that typifies his latter-day filmography: for Sofia Coppola’s Lost in Translation, Jim Jarmusch’s Broken Flowers and once more for Anderson in Moonrise Kingdom, he would channel and cultivate an aged despondency that still charms audiences today.

For Anderson, the painful birth of Rushmore would see him heralded as the forefather of a new kind of filmmaking – respectful of, but not beholden to the past, with a knack for ingenuity and innovation that cannot be tempered. While Rushmore’s cultural touchstones are indisputably overt – the school plays harping Serpico and Apocalypse Now, the raucous soundtrack populated by the Who, Faces and the Kinks, the Charlie Brown Christmas aesthetic – Anderson’s nods to the cultural canon would become increasingly sophisticated as he moved ahead, with references and tributes enriching rather than informing his style.

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Courtesy of: Buena Vista Pictures

America, and the rest of the world, is a very different place in 2018. It’s reflected as much in our latest Wes Anderson offering as anywhere else – Isle of Dogs, preoccupied as it is with environmental degradation, xenophobia, autocratic-populist politicians and the loss of innocence and friendship.

But Rushmore has carved a special space for itself in the past 20 years. It’s at once a window back to where we came from and an indicator of how we move ahead: uncertainly, painfully, but with faith in ourselves and each other. In a time when so many of us are quick to tear at each other and draw lines between opposing camps, it’s worth taking a look back at the weird barber’s son who captained the debate team, founded the astronomy society and saved Latin, and see how he set ego and grandeur aside to build something better and kinder, together with his friends.

That’s pretty wise for a movie that still can’t buy itself a beer.