As a Way of Being in the World, to Be Cool Is to Be a Fascinating Asshole

Ah, Glenn O’Brien, requiescat in pace. Any eulogy for a man such as he was will inevitably go astray if it begins, “perhaps best known for” — what?

O’Brien went to Catholic school, then Georgetown, then film school at Columbia. He was the first editor at Andy Warhol’s Interview. There was a screenplay here and a television show there, a decade of columns for ArtForum. He wrote for High Times and Rolling Stone; he did the Style Guy column for GQ for years and was Creative Director at Barney’s New York. He kept busy and had many irons in many fires. O’Brien could be counted upon to have a point of view. Regardless of any medium, if it was part of popular culture, he was qualified to give his opinion.

Whenever paid professors of cultural criticism forget that pop culture journalism can be just as rigorous and pointed and vital as the work of the tenured caste, O’Brien is one of the guys holding the line for us. I think the primary difference between the inside and outside of the ivory tower is that the meek shall inherit the academy. The fearful have no sense of humor.

O’Brien once tried his hand at stand-up comedy. We’ll be scrambling to retrieve every scrap of him, now that he’s gone. There’s a posthumous publication, Like Art: Glenn O’Brien on Advertising, that was the last thing he did before he died. I’m sure it’s a good one, but the scope of it is too narrow to think of it as the man’s last word. I mean, he also published a book on cognac this year, and it’s not going to be the capstone either. That honor should belong to Cool School: Writings from America’s Hip Underground, published by the Library of America in 2013.

This is a 500-page anthology that he edited. He wrote a 15-part forward to it, collected himself alongside 66 other cool kids, arranged the selections and wrote an introductory paragraph for every single one of them. In short, these are his foundational influences, the keys to that kingdom of cool for which O’Brien has served as arbiter for half a century.

Coolness, as a specific type of charisma, is very difficult to fake because it involves a natural tension of opposites. On the one hand, to be cool is to be fascinating —

witty, astute, colorful, vivacious, communicative, instinctive, fraught, conscious. On the other hand, to be cool is to be an asshole — aloof, icy, bold, capricious, flippant, cutting, vulgar, selfish. As a way of being in the world, to be cool is to be a fascinating asshole.

Cool is a vibe that we can study as somebody else performs it. What cool subjects do cool people talk about? What diction and syntax do they use to talk cool? Does cool have a structure, even an improvised one? This is what O’Brien’s Cool School is getting on to, though he readily admits any anthology of the matter cannot be exhaustive. He could choose 67 other hepcats and formed a totally different product with precisely the same desired result. It’s funny because it’s true. O’Brien was always self-aware, as his “Beatnik Executives” poem once made plain.

So the question of who got in is not an important one to the editor. Personally, I felt there definitely could’ve been more effort to include the ladies. There’s Diane Di Prima, Bobby Louise Hawkins, Iris Owens, Cookie Mueller and Emily XYZ each doing a really marvelous job of cutting down the men around them, just baldly slicing right through the machismo implicit in the brand of coolness supplied by Kerouac, Sinatra, fictive boyfriends and real rapists. But I mean, where’s Patti Smith on Mapplethorpe, Eileen Myles on Kennedy? Nikki Giovanni, Ellen Willis, Diane Wakoski, Ntozake Shange? But OK, not all my cool influences are the same as O’Brien’s.

More at issue than who’s who in the table of contents is the question of what the cool kids are talking about. Interestingly, most of them are talking about other cool kids, their own set of influences. In this beautiful way, Cool School becomes a hall of mirrors. Miles Davis is talking about Charlie Bird Parker. There’s Cassady on Kerouac, Joyce Johnson on Kerouac, and of course Kerouac on himself. Delmore Schwartz on Hamlet, cloudy with a chance of Lou Reed. Gary Indiana making fun of Roy Cohn. Arthur Miller and Chandler Brossard making fun of different kinds of parties. Corso and Kaufman and many others in Ginsberg’s orbit, but not Ginsberg. Burroughs and Brautigan, Tosches and Thompson. The absolute best, most fascinating assholes America has to offer, speculating on the past and future of cool.

Cool seems to be a phenomenon located mainly between the end of Hitler’s war and the beginning of Kurt Cobain’s band. As such, it carries the linguistic baggage of its era, transmitted equally through poems and essays, through fiction and memoir. It uses black and white working class slangs as well as hippie parlance, verbs like flip and nouns like head, interjections like dig and, well, like. The favored curse word is motherfucker (cf. Lenny Bruce, George Carlin, both in this book). Talking is riffing, and either you pick up on it or your don’t. Del Closes’s hilariously on point “Dictionary of Hip Words and Phrases” should’ve been placed closer to the front of the anthology simply for actual use to aid in the comprehension of many of the jazzier pieces.

This begs the question of how cool is structured, if at all. Obviously, there’s a great deal of emphasis on the magic of improvisation. Sometimes it seems like O’Brien put all these pieces in a pile and flung them down at random in choosing what goes where. Sure, there are threads. Maybe two comedians back to back, or maybe four or five mentions in a row about the trumpet. Seems like a lot of the beatnik stuff is in one place and the younger folks who’re still alive appear mostly toward the end. But O’Brien is operating neither chronologically nor alphabetically, neither thematically nor by genre. He goes by feeling. The contents of this anthology are freely associated, but somehow building bridges across the stylish conjectures of the editor’s own experience. Only he really knows why Mort Sahl goes with Bob Dylan, why Chandler Broussard goes with Terry Southern.

Cool School is an unusually fine and eclectic aggregation of the voices that shaped O’Brien and his generation. If it’s got enough macho dudes for a genuine sausage fest, or if Norman Mailer’s “The White Negro” feels like a psycho bunch of essentialist claptrap, or if its romantic portrayals of heroin seem idiotic, that’s the beauty of our hindsight. Cool is a vibe that you soak in, even though some of the wavelength can seem pretty screwed up.

The next generation’s responsibility is to evolve the performance of cool. Take what you want and leave the rest. That’s how this anthology ought to be studied and that’s how Glenn O’Brien ought to be remembered.