Glenn O’Brien’s ‘The Cool School’ and the Futility of Defining Coolness

No good can come of writing about what’s “cool” or “hip,” or of investigating phenomena like “hipsters.” The same goes for searching for misplaced American masculinity, or explaining the habits of people younger than you, yet some brave soul (or Joel Stein) is always willing to step up to the plate in an attempt to hit an unnecessary (and unlikely) grand slam, delivering what they think will be the perfect summation of cool.

It’s all part of one big vicious circle: you try to write about what’s cool, and all you end up proving is that you have no idea; you try to write about the young folks and their strange trends, and you come off as stuffy or an old curmudgeon. If you call yourself cool, you’re sure to have someone telling you that you’re actually the opposite. But vehemently trying to deny what others perceive as your coolness? That only makes you cooler.

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Clearly I’m a skeptic when it comes to writing about “cool,” but Glenn O’Brien is one of the few people whose opinion on the subject I care about. Presumably because I’m not the only one who feels that way, Library of America enlisted the TV Party host, GQ Style Guy, and man who wears many other very nice hats, to compile a handful of pieces “from America’s hip underground,” that try to not only explain what cool was and is, but also decide whether even exists anymore, for a new book called The Cool School. The collection includes writers such as William S. Burroughs, Rudolph Wurlitzer, Frank O’Hara, and a very welcome appearance by Lynne Tillman; funny people from Del Close and Lenny Bruce to George Carlin; musicians like Bob Dylan (it’s probably a law that you have to include Dylan in a book like this…) and Miles Davis; and art-world superstars like O’Brien’s late friend Andy Warhol.

“The scary thing about this project,” O’Brien writes in its introduction, “is that you begin to realize that the underground as we used to know it really doesn’t exist anymore except in our nostalgia for it.” The underground he’s talking about was made up of assorted and often unconnected artists, weirdos, and other free-thinking types — people who, if you were born in the years bookended by the World Wars, your parents would warn you against hanging around or listening to; you’ve got Beatniks, Socialists, bohemians, drug addicts, sex fiends, homosexuals, Jews, African-Americans, New Yorkers, and anyone else who made “normal” folks uncomfortable (and still sometimes do, even in this supposedly more enlightened day and age).

O’Brien points out that he hadn’t paid much attention to “the new class hipster” until he was browsing a bookstore in Berlin and came upon a book by “a bunch of young Brooklynite intellectuals” called What Was the Hipster? — a treatise that, although the author doesn’t mention it, was published by n+1, a publication that certainly passes for cool in 2013 among a certain subset of good-looking people who carry their records to a DJ night in a tote bag with the magazine’s logo on it. But even though we still have our various signifiers of cool, as I read The Cool School, I kept marveling that we used to be better as a culture, that young people used to have more creativity and motivation, that the world was more mysterious and open to discovery, that our lives were more spontaneous before everyone was concerned with taking the perfect selfie. That’s the depressing subtext of this book, which isn’t a treatise on cool, but rather a collection of voices that O’Brien judges as embodying it.

So is anything truly cool anymore, or was anything ever cool at all? What I’ve found, and what this book suggests, is that we should figure out for ourselves what inspires us, and what we wish we could emulate. When I was a kid, I thought Michael Jordan and the members of the University of Michigan’s basketball team dubbed “The Fab Five” were ice cold — I still do — but if I told some people I know that, they’d give me a “Psssh,” and say something snarky about how dumb sports are.

The Fab Five
The Fab Five

But I don’t care what they say — just like I didn’t give a damn when my schoolmates made fun of me for wanting to read some of the authors in The Cool School instead of actually playing basketball with them, or when kids in Abercrombie & Fitch shirts called me gay in high school because I wanted to look like one of the Ramones. In retrospect, doing these things didn’t make me cool in any way, because all of the people I idolized were in some way better than me. James Harden has a better beard than I do, I could never wear a suit the way Cary Grant did, I’ll never be able to look androgynous like Patti Smith or Mick Jagger in their younger years, and I’ll never be able to say something like “I’m so fly, I jumped out the air wearing Gucci” like 2 Chainz, and I’m actually fine with all that because I’ve learned that trying to emulate what you consider cool leads to very lame results. The point of all this adolescent imitation is to find enough influences to start you off on a path of your own.

So, no: cool really doesn’t exist. It isn’t even a state of mind, because if you think you’re cool, then you aren’t. If you call somebody else a hipster, there’s a good chance they’d probably turn around and say the same thing about you, or make fun of you for not being more like them. It’s really all bullshit, everything you’ve been sold is a lie, and one day you’re going to look in the mirror, start humming LCD Soundsystem’s “All My Friends” to yourself, and your kid will report that Pitchfork’s #1 song of 2007 is regularly played on the classic-rock station that all her friends think is the coolest — but in sort of a kitschy, ironic way.