John Rockwell Superboy

The wild real-world playboy adventures of a one-time Superboy

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Apr 19, 2018, 2:00 PM EDT

This week, to mark Superman's 80th anniversary, we spoke to many of the people who have played the Man of Steel — including one whose show never took off. John Rockwell shot a pilot for a proposed Adventures of Superboy TV show in 1961. The series never made it to air (because of sponsor squabbles between Kellogg's and Wheaties, of all things) but you can still see the pilot on YouTube. Rockwell was bummed, but he moved on with his life – and what a life it's turned out to be.

While he got unlucky with the Superboy show, he's lived a charmed existence elsewhere. One time, while working as a lifeguard at the Beverly Hills Hotel, Rockwell saved Hugh Hefner's life. "He couldn't swim," Rockwell recalled in an interview with SYFY WIRE. "He was learning to swim, and he somehow went down in the deep end, so I had to dive in and get him out of there." Rockwell and Hefner became lifelong friends, and eventually, Rockwell ended up living at the Playboy Mansion on and off for most of the 1970s.

Before becoming part of the Rabbit Pack, Rockwell spent some interesting time in Acapulco, where he learned how to play competitive backgammon and also married a Mexican heiress — to whom he says he remains technically wedded. "I haven't seen her in forty-something years, but we're still married!" he says. "We had a deal that if I wanted a divorce, it would cost me a million; if she wanted a divorce, it would cost her $10 million. So it's stayed the way it is."

Superboy Rockwell

Rockwell also has some colorful history in Las Vegas, the town where he once taught Hefner to play backgammon (the Big Bunny's trademark game), and Los Angeles, where he became friends with Lakers owner Jerry Buss, Motown mogul Berry Gordy, and actress Sharon Tate, whom he introduced to her future agent.

"I was in the Bahamas when I heard she got killed," Rockwell recalls. "And that really changed my way of thinking. I said from here on in, I'm going to enjoy life." Which he definitely did – especially during the many nights he logged at both the L.A. and Chicago Playboy Mansions. "Use your imagination," he says with a chuckle. "It was the sexual revolution. It wasn't like it is today."

Rockwell's regular trips to Vegas brought him into the orbit of one Frank Sinatra. Eventually, they began to hang — gambling, sitting in the steam room, hitting on showgirls. At one point, they even fell for the same showgirl, a woman named Jacqueline Douguet, a topless star at the Dunes. One night, Rockwell says, he overheard Sinatra make a $5,000 bet that he could pick her up. Rockwell dreamed up a way to prevent this. He says he trained his poodle, Puff, to walk up to women on his hind legs, offer them a paw, and lead them back to his owner. So he pulled this stunt on Douget: "I paged her, she picked up the phone, she said, 'Who is this?' and I said, 'Somebody's coming to get you.' She turned around, Puff was on his hind legs, and she just went crazy. She thought it was unbelievable."

When the pair headed for the bar to get drinks, the skunked Sinatra followed them. "The waiter comes over and says, 'Mr. Sinatra would like for you to join him," Rockwell recalls. "We said, 'If he wants to join us, he can come over here." A little later, Rockwell spied Sinatra "giving me one of those looks." But the fury passed – Rockwell and Douget ended up dating for a year and a half.

John Rockwell Superboy dog

Drifting away from showbiz, Rockwell became a backgammon pro, taking on the world's best players, from Paul Magriel to Masayuki "Mochy" Mochizuki. Nowadays, he competes annually at the Backgammon World Championship in Monte Carlo, and at all-expenses paid tournaments. (His next one is in Russia on April 22). "A friend of mine said to me, 'John, you've never won a big tournament. So what makes you think you're good?' And I told him, 'Hey, that's the way it goes sometimes. You can be one of the best players in the world, and still lose sometimes. I play all the best players in the world, and I beat them."

It can be a very profitable pastime. "There are a couple of guys I know who play for a million dollars a point," Rockwell says. "This one guy won 148 points one day, so that was $148 million."

Rockwell fondly remembers the time a mutual friend linked him up with another Superboy (it seems inevitable that Supermen of varying vintages should one day become friends). Millionaire heiress Nabila Khashoggi introduced him to Gerard Christopher at a New York dinner party in the early 1980s, and the two actors became good friends. Years later, when Christopher landed the lead in a revived Superboy series, he was unaware that his friend Rockwell had previously (albeit briefly) played the part.

"I had no clue!" Christopher says, laughing. "After I did it, somebody sent me this story about him, and I went, 'Oh my God!' It looked ridiculous, so maybe that's why he never told me about it — because it looks really silly. But that's what people might say someday about my show. It was just really weird to find out later on that he did it, too."

Rockwell has many more stories about his long, post-Superboy life. Friends have pressed him to write a memoir, but he thinks it's too soon. "I never thought I'd make it to 50," he says, "and now I'm approaching 80. There are still a few things I've got left to do."

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