In 1995, Supreme New York was not much more than a year-old skate shop in pre-commercialized Soho. The streetwear brand made a few local waves after slapping their stickers across Kate Moss Calvin Klein billboards around town, but mostly they just happened to sell uncharacteristically expensive tees and hoodies emboldened with a bright red logo (that many would later claim was ripped off from visual artist Barbara Kruger, though Supreme has never come close to admitting as much). In the more than 20 years since, Supreme has managed to become the greatest streetwear brand of all-time. Its mix of authentic skater ethos, insanely limited product runs, and high-class taste—which has translated into T-shirts featuring Lou Reed, Neil Young, and most recently Morrissey, plus design collaborations with elite fashion brands like A.P.C. and Comme Des Garçons—have allowed Supreme to be both out in the open and exclusive at the same time. But its unprecedented run to the top began with a skate video—the grainy, beautiful, black-and-white epic, A Love Supreme.

Videos from the '90s hold a special, nostalgic place in the hearts of skaters, if only because they're pre-Internet. Back then, a new video created moments for kids to bond over in real life, whereas today that connection is, if not diminished, at least re-contextualized by social media. Plus, the inherently crappy quality of the VHS tapes used in the '90s reinforced the gritty, DIY feeling skating has always cultivated and projected. For their first ever video, Supreme went even more retro; it was directed by artist Thomas Campbell, who went on to become one of the most prolific filmmakers in the worlds of skateboarding and surfing, and shot on Super8 film. And instead of punk, it was sweet. A Love Supreme is set to the first two tracks from John Coltrane's album of the same name.

It was not by any means the first skate video to use jazz, or even Coltrane for that matter; directed by Spike Jonze, 1991's Video Days is largely considered one of the most important skate videos of all-time and has a section set to the sax icon's 1957 track "Traneing In." But the 16-minute video did push the concept of a skate video from a cheeky home movie to something more serious. There's certainly a fair share of footage of people actually skating in A Love Supreme, but there are also long, uncomfortable stretches where no skating happens at all. Instead, the music plays while the camera holds on the silhouette of a kissing couple or the out-of-focus headlights of New York City traffic. When the film returns to boards and tricks, the fluidity and dance-like quality of the skaters is in stark contrast to the syncopation and idiosyncrasies of Coltrane and his band. That contrast is made even more apparent because much of the film was shot at frame rates other than the standard 24 FPS, and when the footage is sped up, you feel like you're watching jazz in motion. Like its music, the film is chaotic, surprising, engrossing, and hypnotic.

Still, the almost too-cute play on words between Supreme and A Love Supreme distracts from the deeper parallels between jazz and skating. Perhaps more than any other sport, skateboarding is inherently improvisational—there's no "right" way to use a park bench or hand rail to execute a specific trick. And despite what the X Games may suggest, the actual culture of skating is built more around socialization than competition. There are no scoreboards. Even though it's often thought of an activity for misfits and troublemakers, there's actually something beautiful about skating's democratic qualities. Supreme was able to make a video that displayed this beauty while creating something warmer and more inviting than anything that came before it without dulling skateboarding's rough edges.

When he released A Love Supreme in 1965, Coltrane described it as the fusion of his passion for jazz music and his faith in God, and the album has been worshipped as a touchstone ever since. Similarly, the transcendent quality of Supreme's A Love Supreme inspired unwavering faith from generations of believers in the brand and set the tone for their iconic and artful simplicity.