One of the first films I remember watching with my dad is To Sir, With Love. The 1967 Sidney Poitier film is about a Californian/Guianan teacher heading up a class of juvenile delinquents in the East End of London. My dad had seen it in the theater, but we had to settle for a VHS copy in the late ’80s.

The film’s turning point comes when Poitier’s character, Mark Thackeray, having been pushed to the breaking point, announces that he’s going to treat his class of teens like adults, offering to hear them out, discuss things affecting them, and teach the kinds of things you’re expected to know in the real world, like how to fill out resumés.

That’s what Glenn O’Brien’s “Style Guy” column was for me, and one of the main reasons I wanted to work at American GQ (although the column technically started at Details). When I eventually ended up in the hallowed halls of Condé Nast a few years ago, part of my job was to translate his revered column from the magazine to the website. Strangely, it’s one of the aspects of my time there I can remember pretty clearly.

RIP to the legendary Glenn O'Brien. ?: Robert Maxwell for @GQ

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So the news that he passed away yesterday felt like losing a surrogate father. I didn’t learn the finer rules of menswear from my own dad. I learned how to tie a bow tie on YouTube. I learned how to buy a suit that fits on StyleForum. And I learned how to cop Supreme from SuperFuture. But what Glenn O’Brien taught me is how to throw the rules out the window when I didn’t agree with them.

When I left GQ to return to Complex, I worked closely with the Four Pins team. I  remember the day we published Glenn O’Brien’s legendary roast and rebuttal to being replaced as “The Style Guy.” It demarcated an end of an era and a changing of the guard. The future of men’s style conversation wasn’t in a slickly-produced print magazine (though they still have a certain value), it was on a multitude of screens and an endless feed of community-based social media.

For most of our audience, it’s notable that the first words in Supreme’s 2010 Rizzoli book are his. Written in O’Brien’s inimitable style, he ties in anecdotes about skating as a teenager, John Coltrane, and multiple references to artists from Barbara Kruger to Nam June Paik. His writing establishes a canon that ties the work of William S. Burroughs to Greek philosopher Diogenes, reinforcing their relevance with modern culture. He was forever a champion of the obscure.

J. Berliner / BEI / Shutterstock

In fawning over Supreme’s long sleeved T-shirts and reinforced khaki work pants, he likens the quality of the clothes to Hérmes, years before Louis Vuitton and Supreme became strange bedfellows. But what he’s always demonstrated is an unmatchable level of cultural fluency. He got it. He understood the undertones and nuances that separated cool from wack, and was able to summarize how “what was” informed “what is.”

TV Party, his seminal public-access show from the late ’70s and early ’80s attracted guests like David Byrne, Jean Michel-Basquiat, and Fab Five Freddy. One of my favorite episodes featured Blondie’s Debbie Harry, and German countertenor, Klaus Nomi  and there are a ton of them currently available for streaming. TV Party’s absurdist undertones and subversion of the variety show format predate the kind of cannabis-enhanced programming you’ll now find on adult swim. It’s a tone of voice that lives on in his writing — his archived blog posts are definitely worth a read.

Speaking of cannabis, Glenn O’Brien invented the title of “Editor-at-Large” at High Times, a distinguished label for the type of person who preferred to work remotely rather than be tied down in an office. It’s a title I once held for this very site, before I had to start reporting into the office every day. But that’s the kind of foresight he had; O’Brien saw a future in which the best kind of job was an ambiguous one, where what you actually did remained ever so slightly dubious.

But most of all, Glenn O’Brien was a one-man crash course in classic alternative culture. In some ways, he was the last bastion of the “old New York” so many people lament about missing — Warhol’s warehouse, the days when SoHo was covered in SAMO tags, and struggling creatives could afford to live downtown. But in another, he was also the person who believed that environment could still exist in the minds of the younger generation. And really, that’s what youth has become.

It’s not a specific demographic. It’s not a certain way of dress. It’s the ability to keep your mind elastic enough to regularly bounce between the past, present, and future.

In a piece about the value of modesty for L’Officiel Hommes, he wrote, “I could have been a rock star, but I wanted to get enough sleep and take better care of my skin. I could have written the great American novel but it’s not all that great to be American, and novels aren’t very novel now. They’re too long, even from the best writers and in the end, novel, so what? I’d rather stay in my own character. I’m good at it already.”

There will never be another Glenn O’Brien. But what he’ll always remind us is that there’s a lot more value in being yourself.

  • Main & Featured Image:Bobby Grossman
Words by Jian DeLeon
Editorial Director

Jian DeLeon is the Editorial Director at Highsnobiety. He is based in New York.

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