Written by John Winters   

How can there be such a thing as a canon of hip literature?

The publishers of “The Cool School: Writing from America’s Hip Underground” (The Library of America, 471 pages) hope the new collection of so-called hip writing will go some way toward defining and/or solidifying one.

But to be hip or cool, by definition, means to be a rebel, to tear down walls, buck the institutional will and stand apart from the maddening, ordinary crowd. Writing of this kind should defy simple categorization and easy corralling. Right in these pages, Anatole Broyard, one of the high priests of cool, tells us that for the hipster, language is coded, polemical, aggressive, solipsistic, and too reckless for its own good. That hardly sounds like the making of canon fodder.

Yet, with the imprimatur of The Library of America, this book will be viewed by some as possessing some sort of definitiveness. Hence, we’re back to where we started; with paragons of writerly cool being mainstreamed into what could be considered a pleasant coffee table book. Even worse, the volume’s editor, Glenn O’Brien, is pictured on the back cover in a bow tie and tux. He should have paid closer attention to those 1993 Gap ads featuring Kerouac wearing khakis – a serious co-opting of cool. Jack’s getup was way more hip than formal wear. Just ask Madison Avenue.

In 2013, many of the essays, stories, lyrics, comedy routines and poems included in “The Cool School” seem more historical then edifying. The revolution is over and the bad guys won. These pages are rife with dreams and unrealized hopes, dispatches from a time when Neal Cassady could drive a bus of acid-baked hippies halfway across the U.S., or Hunter S. Thompson could cut deep into the heart of the American Dream or savage a corrupt politician’s reelection campaign. Their writing reminds us of how far we’ve come – or, how low we’ve sunk. Soon, we’ll be buying weed at Store-24, and our only political insights will come via posts on our iPhone or through the twisted megaphone of Fox News. Today, Lester Bangs’ music journalism would have to fit 140 characters, Lenny Bruce would have his own HBO special, and Miles Davis might not get a record deal. Meanwhile, my mom loves George Carlin, even his “Seven Dirty Words You Can’t Say on Television” routine.

All these writers and artists are included in “The Cool School,” and many seem de-fanged by the march of time, their words as subterranean as a skyscraper. And I feel old. That’s not to say that all of this is an exercise in nostalgia: Some of the pieces presented here feel timeless and fresh. After all, the entries date from the 40s to the 2000s, so there's bound to be a mix. It’s just that after watching buildings crumble, footage from never-ending wars, sex-drenched cable and violent video games we’re a pretty hard lot to shock nowadays.

That said, some of the writing here is still relatively outré. The selections from Art Pepper’s autobiography depicting his sexual exploits could make an aging hedonist blush. His stated love of drugs is honest and depressing, bordering on shocking. Normal Mailer’s seminal essay, “The White Negro,” meanwhile, has not aged well, but it shows how the mainstream media once embraced “big” ideas and had the nerve to publish things that today might not pass the PC sniff test. There’s also the hipster riffing of forgotten writers like Lord Buckley, and prose by Terry Southern, Alexander Trocchi, Nick Tosches and Bobbie Louise Hawkins that would be considered first rate in any era or by any standard. While “The Cool School” features too-few women writers, marquee names abound: Burroughs, Warhol, Sahl, Corso, O’Harra, and the Grand Poobah of them all, Dylan himself. (No Bukowski, Ginsberg or Selby?)

Jazzers, junkies, journalists and journeymen jockey for position in these pages with poets, authors and songwriters. The eclectic mix of writers speaks to the ever-expanding definition of what was and is considered hip.

The collection’s strong points are its attitude, always an important component for anything considered hip, and the rhythm of its language. If time has dulled the sharp edges of the once-bold, scandalous words and ideas in “The Cool School,” it cannot stifle the way many of these words swing. Lastly, humor and pathos are present throughout the volume. For to be hip means to know the real score and be able to laugh at man’s shared existential hell or sing the blues over our universal doom.

All these elements are the legacy of hipster culture, and “The Cool School” has ample helpings of each. The collection is a good place to start for those looking to discover or rediscover the revolutionary power of words. Even if that revolution died in Dallas, Memphis, Altamont, Spahn Ranch, Vietnam, the Ambassador Hotel, Iraq, the World Trade Center…

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