Daniel Pinchbeck and the New Psychedelic Elite

Calm is how he seems tonight, sipping an almond shake at a dimly lit vegan restaurant in the East Village, talking about his childhood. "At some point in Carlos Castaneda's books, he asks Don Juan what he was like as a child, and Don Juan says, 'I have no personal history,' " Pinchbeck says with a strange half-grin. "I feel that way too, pretty much. Just trying to stay open."

But few have been as shaped by their upbringing as Pinchbeck. An only child, he was raised in Manhattan by his parents, Peter Pinchbeck, a little-known abstract painter, and Joyce Johnson, a Beat author who raised Daniel as a Jewish atheist. Johnson was Jack Kerouac's girlfriend — "an interesting young person, a Jewess, elegant middle-class sad and looking for something," is how he described her. He exhorted her to meet him in foreign lands — "we'll do our writing & cash our checks in big American banks & eat hot soup at market stalls & float on rafts of flowers & dance the rumba in mad joints" — but they were mostly together in New York, making love all night before hitting the city streets to pick up the New York Times review of On the Road in the morning. A polite muse, she watched in the wings as Kerouac became a superstar, standing backstage when a TV interviewer asked him, "What is it you're looking for, Jack?" He responded, "I am waiting for God to show his face."

Johnson brought up Pinchbeck in New York, where she edited books by Allen Ginsberg and Abbie Hoffman. When young Pinchbeck was two and in his highchair, Hoffman appeared at their window after the Chicago Democratic National Convention, screaming, "I have a book!"; upstairs, he grabbed a banana out of Pinchbeck's hand and astonished him by breaking it in half and eating it. Similarly grand gestures by male role models were the stuff of Pinchbeck's adolescence, with trips made to his father's loft and that of neighboring male painters in SoHo after his parents' divorce, all the men in a "mad, iconic battle against the establishment," says Pinchbeck. Like a true Beat dad, his father showed little interest in him and even said he wished he had never had a son.

"And I was the classic paradigm of one who can't make it in the aggressive social reality of high school, so I geeked out on Dungeons and Dragons, poetry, chess and go," says Pinchbeck. He toted Ginsberg's books to school, taunted by his classmates when they opened one to find a poem called "Sweet Boy Give Me Your Ass."

For a long time, Pinchbeck, who spent part of his adolescence in a body cast with a crippling back ailment, was afraid of sex, of his fragile body being intruded upon by another. After dropping out of Wesleyan University in the late Eighties — a nerdy New Wave kid, he didn't fit in at a college of prep-school Deadheads — he sought to cure himself of this condition, say friends, by hanging out at a bar near Columbia University once popular with the Beats and hitting on every girl there until he no longer had any fear or shame, and caught a couple, too (today, friends note with head-shaking wonder Pinchbeck's skill at landing beautiful women). "I always say, 'You haven't lived in Manhattan if you haven't thrown up out of a cab or fucked Daniel Pinchbeck,' " says an old conquest. "He will yell and whine and make you date him."

He applied a similar focus to becoming successful. In the early Nineties, Pinchbeck co-founded the literary journal Open City with Thomas Beller, an author of wry coming-of-age fiction and Parker Posey's ex-boyfriend, and Robert Bingham, the mad scion of a Southern newspaper family who seemed like he might become his generation's Robert Stone. For a few years, they were the talk of the town, publishing and befriending promising new authors and indulging their taste for sex in the constant pursuit of erudite high-cheekboned nymphs. When the scene began to fall apart, with Bingham soon dying of a heroin overdose with the galleys of his first novel on his desk, Pinchbeck was left at loose ends, with two novels rejected by publishers and magazine work not entirely forthcoming. (He now distances himself from this world he once strove to dominate: "Almost anyone involved in my generation's literary books is [now] holding on to a world perception that is only leading us to destruction.")