Neal Cassady won’t go away. The wild young man dashing madly down the highways of experience, liberated from conventional restraints and searching for sex and salvation in the American night, sent chills of horror down the spine of respectable society in 1957, when Kerouac immortalized him as Dean Moriarty in On the Road. A few years later, just when America thought it was safe to drive again, he came roaring back, in the flesh this time and crazier than ever, as the pilot of the bus Ken Kesey and his “Merry Pranksters” took cross-country in the psychedelic 60s. His mad appetite for pleasure and his speed-crazed monologues, recounted faithfully by Tom Wolfe in The Electric Kool-Aid Acid Test, made him a counterculture folk hero. Survivors of that era still speak and write of him with reverence.

Best of Chicago voting is live now. Vote for your favorites »

Carolyn tells of blissful periods of dazzling romance and mind-expanding conversation interspersed with Neal’s gut-wrenching departures, betrayals, infidelities, and an apparent callousness that brought a new dimension to the term “mental cruelty.” After a while there seem to be no words to describe such a man; Kerouac’s brusquely affectionate “mindless cad” barely begins to suffice. When Cassady finally names himself, in a letter written to his wife from prison, as “Neal, the REAL heel,” one can only nod one’s head in dazed agreement.

There’s a darkly hilarious account of the sordid paradise William Burroughs constructed for himself in the late 40s in a ranch house in Algiers, Louisiana, just outside New Orleans. Kerouac’s tragic decline from visionary young novelist to babbling drunk is likewise drawn with heartbreaking clarity. Ginsberg emerges as a saintly figure, kindly and nurturing, distributing gifts to the Cassady kids and gently prodding his friends in a vain attempt to get them to abandon their sorrowful self-absorption and experience the joys of being.

Surprisingly, Cassady himself hinted as much. It’s somewhat shocking to discover that the very things for which he’s usually venerated–his sexuality, his shedding of society’s conventions, his frenzied hunting for trips and kicks at whatever cost–apparently made him shudder in his calmer moments. Carolyn says that fan letters from Kerouac’s readers made Cassady “flinch with guilt”; Kerouac’s “glorification of his antics in print . . . made him uneasy. He wasn’t proud of this side of his nature; he had tried very hard to overcome it.”

There’s scarcely a hint here of the tormented, disintegrating wretch Carolyn portrays in Off the Road: “I can’t help it anymore [she quotes him as telling her]. I don’t know where else to go. I’m a danger to everyone–to myself most of all. I keep swearing I’m going to stop making an ass of myself, but then I get in a group and everyone stares at me, waiting for me to perform–and my nerves are so shot, I get high–and there I go again. I don’t know what else to do–it’s horrible.”

Neal fared little better. A psychic reading revealed his past lives and purported to explain his self-destructive impulses. Another praised his “spiritual attributes” with such eloquence that it sounded like “one long mystical prayer,” and the woman doing the channeling wept at its beauty.