Much later, Anderson turns to the Stones’ “I Am Waiting” for the film’s near-climactic “November” montage—a series of scenes in which the characters are all at their lowest, eating lonely Thanksgiving dinners in a state of depressed suspension. Over flourishes of harpsichord and dulcimer that echo Mothersbaugh’s score, Mick Jagger sings about an obscurely defined “waiting for someone to come out of somewhere”—an uneasy sentiment that reflects the holding pattern they’re all in, uncertain of when things will change, or who or what might be the catalyst. It’s wistful and worried, and when Jagger unleashes on the refrains, it captures their own repressed howls.

Rushmore’s “angry young man” vibe also finds potent expression through The Who, whose miniature rock opera “A Quick One While He’s Away” (specifically, its final movement) crashes and caterwauls behind the escalating war between Max and Herman. As Anderson’s longtime music supervisor Randall Poster explained to Vulture, “What’s great about that song in particular is that it’s sort of a dialogue, so we have the twin sides of Blume and Fischer”—even though its lyrical exchange, between a man and his unfaithful lover, doesn’t track literally. (Even less so if you consider “A Quick One” as an extended metaphor for Pete Townshend’s childhood sexual abuse.) What it does do, however, is provide some much-needed levity to these scenes of two wounded guys who are trying desperately to hurt, even kill one another. Townshend’s repeated “You are forgiven” offers ironic counterpoint to a bitter grudge match that might otherwise read as genuinely unnerving. In Anderson’s hands, “A Quick One” also joins the cinematic pantheon of “cool songs to walk to in slow-motion.”

Anderson employs another wink for Max and Herman’s reconciliation, using John Lennon’s sappy-sweet “Oh Yoko!” as the backdrop to a montage where Max tries to help a bottomed-out Herman get into shape and win back Rosemary. While Herman probably (hopefully) isn’t calling out Max’s name in the bath, it suggests they’ve found a similarly codependent companionship—that all they really need is each other. Along with the breezy saccharinity of Chad & Jeremy’s “A Summer Song,” which lilts along during the early scenes of Max and Rosemary’s burgeoning friendship, it’s one of Rushmore’s more knowingly precious moments. Although, in both cases, their straightforward pop simplicities are a feint, a setup for the intrusion of complicated reality into easy-listening fantasy.

Hal Ashby’s Harold And Maude also looms large over Rushmore, so it makes sense that Anderson and Poster would turn to its bard, Yusuf Islam (formerly Cat Stevens), who lends a similar, similarly layered form of sentimentality here in his two contributions. His 1967 hit “Here Comes My Baby” plays over scenes of Max, Rosemary, and Herman hanging out in happier days, the lyrics—pining for a woman who’s “Never to be mine / No matter how I try”—belying the music’s jaunty tone, much as the group’s cheerfulness provides cover for Max’s own longing for Rosemary, as well as her furtive flirtations with Herman. Later, the 1971 deep cut “The Wind” punctuates the moment when a newly humbled Max slowly begins rediscovering himself, its meditative lines on learning from your mistakes peacefully unfurling while Max flies a kite (which is maybe just a tad on the nose there) and plots his newest club. Poster said he considered getting Stevens’ music in front of a modern audience as one of his personal coups, as he’d become much more reluctant about licensing his work in the ’90s. (Hearing your song in the background of Airwolf will probably do that.)

In addition to liberating Stevens’ records from the used bins, the Rushmore soundtrack’s greatest legacy is that it did the same for a handful of other British Invasion-era artists who had by then fallen out of favor, or who didn’t have the same legacy protection as the Big Three of The Stones, The Kinks, and The Who. Unit 4 + 2, for example, who had scored a No. 1 hit with 1965’s “Concrete And Clay,” but struggled to match its success and had largely been forgotten. The song’s jaunty, vaguely Latin-jazzy bounce was not only ideal for the sequence where Max circulates his petition to save Latin. It was also one of those perfect, crate-digger rediscoveries—the kind of “wait, you’ve never heard this?” moment that Anderson had only hinted he was capable of back when he was dropping deep Love cuts into Bottle Rocket. Anderson’s ability to pluck out those kinds of overlooked golden oldies, while casually referencing both The 400 Blows and Serpico, proved Anderson’s mettle as a consummate pop curator, much like his contemporary Quentin Tarantino.

Nowhere was this expertise—and the power it wielded—more evident than in Rushmore’s two most iconic tracks. In 1999, The Creation was one of those secret handshake bands beloved primarily by other musicians from The Sex Pistols to Jimmy Page (who nicked their use of a violin bow on the guitar), but little-discussed outside of psych-rock connoisseurs. The group’s debut single “Making Time” had been just a minor UK hit in 1966, and the lack of a proper album largely kept The Creation unknown to all but the most ardent scourers of old 45s. But Rushmore affirmed the song as one of the all-time great mod/garage/psych anthems. It chugs beneath the film’s opening yearbook montage, its lyrical push against the rut of “always singing the same old song”—as well as the sardonic aside of “People have their uses”—presaging both the film’s themes of rebellion and Max’s manipulative ways. It’s one of the great marriages of music and movies.

Ditto the use of “Ooh La La” by Faces, a band that was by then long removed from its early-’70s heyday, and largely remembered, if at all, as the springboard for Rod Stewart’s solo career. The group had disintegrated around the recording of the eponymous 1975 album it hails from, which Stewart slagged off in the press, ending in sour defeat an impressive run that had stretched from its influential Small Faces days. “Ooh La La” was also an anomaly in Faces’ catalogue for featuring Ronnie Wood on lead vocals, and as a result, it, too, had the ring of freshly unearthed rarity when Anderson featured it in the film’s final dance scene—here as a special request that’s been pre-arranged with the DJ by Max himself, ever the precocious old soul. The scene is one of the most resonant needle-drops in Anderson’s entire catalog, with Wood offering a warning wrapped inside a wistful lament about the unavoidable pitfalls and heartbreaks of youth, while all the assembled characters sway toward their final curtain call.

Like the rest of the film, it’s a moment that feels completely, dreamily unmoored from time, which allows it to be timeless. Although Rushmore is ostensibly set in the then-present, there are few late-’90s markers, beyond a few decidedly modern cars. The school uniforms and Murray’s inconspicuous, unchanging suit help maintain the illusion, as does the very deliberate lack of cell phones and computers. But it’s largely through its music that Rushmore taps into its yearning for an undisturbed, if fuzzily defined midcentury—a longing that was mirrored in the way music was already shifting outside of Rushmore, too. By 1999, the diminishing returns of “alternative rock” were evident in the glossy pop-punk glurge and bubble-grunge that was all over its fellow teen movies that year. They were soon to be swept aside by a new crop of moddish garage-rock revivalists (led by bands like The White Stripes, The Hives, and The Strokes) who seemed similarly interested in pretending the ’80s and ’90s had never happened. Many of them dressed in louche, loosened neckties, cultivating their own aura of preppiedom gone to seed. Two minutes ago, most of those New York bands had been cigarette-sneaking prep school kids themselves.

It’s difficult to gauge just how much influence Rushmore might have had on fostering that scene, or whether it was simply caught up in the larger flow. The year Rushmore debuted in limited and festival run, for instance, Rhino had already released a four-CD reissue of the indispensable comp Nuggets: Original Artyfacts From The First Psychedelic Era, 1965-1968, putting other forgotten ’60s garage bands on the radar of many a blooming hipster. Mod and garage nights, where DJs spun old R&B and freakbeat cuts for kids playing Quadrophenia dress-up, were already taking hold in college town clubs. (I would know.) But Rushmore fed into that growing retro craze, and it’s safe to say it played at least some part in introducing those charms to a new generation. Like Max, they were looking for their own shortcuts to appearing older and more sophisticated, and hungry for something beyond recycled Green Day and Stone Temple Pilots riffs. And they definitely saw, probably even loved Rushmore. By the time Rhino commissioned a second volume of Nuggets in 2001, the whole thing kicked off, naturally, with “Making Time.”

What is undeniable is just how much influence Rushmore and its soundtrack had on Anderson, for better or worse. On the one hand, his song choices have become a quirk as familiar as his symmetrical framing and Futura fonts; any worthwhile Wes Anderson parody demands some sort of jangly ’60s pop trifle. But it also set a bar for meticulously selected music-nerd picks that he would continue to raise, in tandem with his movie’s budgets, while digging up new/old sounds for The Royal Tenenbaums, The Life Aquatic With Steve Zissou, and so on.

That these soundtracks have remained popular, even as streaming has largely rendered the soundtrack redundant, is testament to their staying power. And it’s proof of the difference between a soundtrack created by committee and one by a filmmaker who approaches it with purpose, even as Anderson’s eclectic, playlist-shuffling approach has since become unremarkably commonplace. It’s likely Rushmore will still be a paragon of the form another 20 years from now, when the Wes Anderson equivalent of 2039 will be mining his own nostalgia by cuing up Smash Mouth.