Soon Gordon was a player, traveling on the Concorde in silk suits and shades; at his height in the '80s, his management company, Alive Enterprises, was grossing upwards of $22 million a year. In his spare time he slept with models, dated Sharon Stone, and married (then quickly divorced) a Playboy Playmate he'd met at Hef's mansion. He drove a white Bentley and a white Rolls, and rattled around a succession of absurdly large homes; his Brentwood spread had so many rooms, there were six he never even entered.
He was living the life, beyond anything he'd ever imagined. What more could a guy like him want? Certainly not a bunch of orphaned kids to take care of. What on Earth would Shep Gordon do with a bunch of orphaned kids?
Wealth and fame in the land of pop music didn't seem to be in the cards when Shep was a boy. He was raised in a Long Island suburb by a CPA father and a formidable mother; he always felt she preferred his older brother. "I was sort of the ugly duckling, and my brother was the perfect person," says Shep, pleasantly paunchy now, with silver fringe ringing the base of his scalp. At 66 he exudes an everyman mildness that's difficult to reconcile with the go-go deal maker he used to be.
A future veterinarian, Shep's brother loved animals—particularly his mutt, Skippy, who didn't care for Shep; as a result, "I spent most of my youth in my bedroom with the door locked so I wouldn't get bit," Shep says. "Which in some ways was very good because I had to become independent. I watched TV, I read, I daydreamed—about getting out of the house and having a life."
When that blessed day finally came, Shep chose the farthest school the New York state university system had to offer: SUNY Buffalo. Then he went to New York's New School for Social Research for a master's in sociology, supporting himself with odd jobs, the oddest of which was shipping backless garments to funeral homes for corpses to wear. In 1968 he headed to Los Angeles, lasting a single day as a probation officer before meeting up with a college friend, Joe Greenberg, at the fabled rock 'n roll mecca the Hollywood Landmark hotel. Jimi Hendrix was hanging out there, along with the Chambers Brothers and Janis Joplin (who, on Shep's first night, made her presence known by having sex, loudly, on the pool's diving board). Shep and Greenberg were told they looked like rock managers; furthermore, there was a fledgling band living the the Chambers Brothers' basement—Alice Cooper—that needed one. Desperate for a gig but clueless about what such a job might entail, the buddies from Buffalo figured they could fake it. Alice Cooper likes to say that his and Shep's long, fruitful relationship was forged on lies: In their first meeting, Shep said he was a manager; Alice said he was a singer.