In The Cool School, out this month, Soapbox author and GQ columnist Glenn O’Brien has culled excerpts from memoirs, novels, comedy routines and song lyrics by the hip outsiders of America’s formative decades—as O’Brien puts it, a textbook for Outlier Lit 101. Below, we bookmark eight.

Who: Lenny Bruce (1925-1966)
What O’Brien Says: “Bruce was the first free association comic rock star and he never met a subject he shrank from, even as his candor earned him arrests.”
What We Say: Comic and social critic Bruce (pictured right) is a cultural touchstone beloved by many and reviled by the rest. Get to know him and decide which side you’re on.

Who: Richard Hell (b. 1949)
What O’Brien Says: “When [his] band discovered a bar with a good PA system called CBGB, they set the tone for a movement with a jagged beat, spiky hair and ripped duds.”
What We Say: He changed his last name from Meyers to the edgier Hell (above with Elvis Costello), but make no mistake that the revisionist rocker was one of the most genuine voices of punk.

Who: Lester Bangs (1948-1982)
What O’Brien Says: “He flaunted an attitude every bit as bad as the rock stars he took on as a critic and interviewer.”
What We Say: Forget what you know as music writing and dig into the work of Bangs (left), who held musicians and their work to impossibly high standards with an unparalleled voice.

Who: Joyce Johnson (b. 1935)
What O’Brien Says: “The Beats were not entirely a boys’ club, but their scene could pass for one most of the time and Joyce Johnson’s 1983 memoir provides an alternate take.”
What We Say: Don’t hesitate in picking up Minor Characters, Johnson’s gimlet-eyed memoir, which exposes some never before known aspects of life with the Beats.

Who: Herbert Huncke (1915-1996)
What O’Brien Says: “Huncke’s life was a relentless adventure: hobo wanderings in the Depression, pre-war junkie hustling, wartime Merchant Marine service, and tribal elder to Burroughs, Ginsberg and Kerouac.”
What We Say: Huncke’s 1965 journals are as great a window into the era as one can hope to find.

Who: Henry Miller (1891-1980)
What O’Brien Says: “Henry Miller was the archetypal drop-out before there were drop-outs, quitting family, job, and the U.S. to lead a bohemian existence in Paris.”
What We Say: Back in the States, his hilarious, astute account of a drunken Hollywood dinner party in The Air-Conditioned Nightmare is case of reverse culture shock at its best.

Who: Lynne Tillman (b. 1947)
What O’Brien Says: “Lynne Tillman came up in the punk/New Wave era but she wasn’t a punk, more a “Pictures Generation” classical novelist adept at exploring the new art world.”
What We Say: Those who’d rather curl up with their cat than attempt serious art appreciation will find their heroine in Tillman’s The Madame Realism Complex.

Who: Eric Bogosian (b. 1953)
What O’Brien Says: “In the nineties we found ourselves in a weird place, with poetry as we had know it dissolving before our very ears, morphing into stand-up comedy… Quite unhip. We were rescued…by such solo performers as Eric Bogosian.”
What We Say: His writing on the dark side of achieving the American Dream will earn your allegiance, but you probably already loved him from Law & Order: Criminal Intent.

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