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In late February 1981, L.A. was being pounded by rain, day after day, a regular monsoon that affected every aspect of daily life. It was during that deluge that I drove up to the Playboy Mansion, ready to attend my first editorial meeting as the new West Coast editor of Playboy. This was my first job at a huge, national magazine, so I dressed accordingly. Slacks. Tie. Sport coat. Not the jeans and T-shirts I’d worn at my previous job.
There, sitting around a huge dining-room table neatly arrayed with notepads and freshly sharpened pencils for each participant, were my new colleagues from the magazine’s headquarters in Chicago and the satellite office in New York. These were giants in the business — people who hung out with Norman Mailer and Helmut Newton. But you wouldn’t know it to look at them. They were dressed like slobs. Jeans. T-shirts — exactly what I had just escaped. I was puzzled. Is this how the best and brightest dress for meetings with the boss?
Then Hugh Hefner entered at his usual warp speed. And I had a realization about Playboy: It’s impossible to underdress if your boss wears pajamas. As Hef spoke (“Someone just told me it’s raining. Is that true?”), I had another realization: This is a man who exists in such a rarefied realm that he doesn’t even experience weather.
For 34 years, Hef would be a factor in my life. Casual, down-to-earth, funny — but also one who regularly expected the impossible. It was not unusual for a story to go through 12 or so rewrites to meet his exacting standards. Once, when the magazine was publishing its Vanna White pictorial, I knew Hef would be obsessed with the text. (Yes, he cared as much about the words as he did the pictures.) Since Vanna’s story was important, I volunteered to be the first writer, knowing that Hef — being Hef — would hate every word I wrote and insist that someone better on the staff take over. I’d be free. I was right. Another staffer tried. She failed. And another. And another. But I had outsmarted myself. After every staff member had come up short, Hef moved back to the front of the line and started over. Trust me, he was no easier to please during my second at bat.
If I ran a magazine, I would hire Hef as the copy chief. No detail escaped his eye; every caption had to fit exactly. The magazine was the great love of his life. It had to be perfect.
Despite his image, he was devoted to his family. Even his ex-wife worked for him. His mother-in-law worked for him. His father was too conservative to read Playboy but not too conservative to act as his CFO. His daughter was CEO. His son is chief creative officer. It was the same at home — he had family dinners more often than the Duggars. His mother, who lived to be 101, had trouble making it to dinner on her own, so he would regularly send a car for her. She lived in Arizona.
Of course, then there’s the other Hef. The nude women. The pajama parties. The grotto. The celebrity friends. The seven girlfriends. The jet. The limos. Even after 34 years, I didn’t know that Hef well. Party Hef wasn’t keen to mix his business life with his personal life.
Hef didn’t much like having employees hanging around his parties. He never asked friends to be in the magazine and never expected his editors to go lightly on his pals when covering them in the magazine. That must have been tough for him on some level. At various times, regulars at the mansion included Warren Beatty, Jack Nicholson, George Plimpton and other marquee names, great cover lines for any magazine. The parties would bring out significantly more wattage. Even Hef’s high-powered staff would seem shabby in that group.
Still, the business Hef was no normal editor — he was the first celebrity editor. Does any other magazine have theme music written by Cy Coleman? There were reminders of work and Hef wherever I went. On my desk still sits my favorite memento: the Hef bobblehead that was popular during The Girls Next Door‘s run on E!
Name one other editor who was famous enough to be a bobblehead. You can’t.
A version of this story first appeared in the Oct. 4 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.
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