Hef, the Ultimate Not-Me

The opposite of hero worship is negative self-definition that tells you who you are not and could never be. Such anti-role models can influence a life as much as those you admire and want to emulate.

Hugh Hefner has always been at the top of the not-me list and, now that the geriatric Playboy founder is exposing himself to ridicule by marrying a 24-year-old Playmate ("It will be," says Letterman, "an open-casket ceremony" with Leno adding that the bride is planning a June wedding and an August funeral), it's time to examine my complicated feelings about the man.

At 84, Hef is two years younger, we both edited successful magazines and half a lifetime ago I was wooed to be his successor.

In 1969, over lunch in Chicago, Playboy's publisher, Hefner's oldest friend, is complaining about the struggle to curb such excesses as perpetual parties and a seldom-used but always available 727 and, at the same time, subtly probing to see if I too might go hog wild over such amenities.

It is an out-of-body experience. I listen and nod, while an inner voice questions my sanity over the absurdity of putting myself atop an empire of sensual pleasure against all evidence of my nature and experience. After 45 years of being Mr. Responsible, how could I think of plunging into the glorious chaos of every boy’s dream, with permission--no, mandate--to spend days, and nights, in an X-rated world? Could I?

Even as I wallow in fantasy, my mind is mocking me with a movie memory of a fat Nero, lounging in a palace while near-naked maidens dangle grapes over his mouth.

By coffee, the publisher seems satisfied with my stability and suggests dinner with Hef that night at the mansion. “He’s going to fall in love with you and offer you the job on the spot,” the publisher says, then hesitates. “If he does, what will you say?”

Fantasy can only go so far. I answer honestly: “I don’t know."

He seems unnerved. “Unless you’re sure you’ll say yes, I can’t take you to meet him.”

So it’s settled, but I feel entitled to a small indulgence. “Does it work this way,” I ask, “with women, too?"

I should have known it was not meant to be a year earlier at the 1968 Democratic convention when fellow delegate Jules Feiffer, after defeat of an anti-Vietnam resolution, was taking me to Hefner's for consoling drinks and steak. But, as young protesters were being clubbed, we got off the delegate bus to join them in Grant Park and were separated by a cloud of tear gas. I ended up alone with a room-service sandwich and burning eyes.

Now, as quiet-living octogenarian, I watch in bemusement as Hefner in a state of hormonal excitement does TV interviews with his fiancée and shrugs off sneering descriptions by a former Bunny as "a strange old man who popped Viagra pills like they were Skittles and doled out $1,000 a week in cash from a safe to his various 'girlfriends.' There’s a word for that kind of arrangement."

Well, yes, but I also recall a time when a friend was asserting my moral superiority to another shameless contemporary who spent his time eating the world and all that it has to offer. My response was to ask, "But which of us will be having a better time tonight?"

Do I feel that way about Hefner now? No comment. I just wish my not-alter ego a happy honeymoon and a long life.

Viagra Pajama Party

At 83, Hugh Hefner in his Mansion is looking more like the faded silent-movie star of "Sunset Boulevard" than the host of the most swinging venue of the past century.

As a one-time draftee to be his successor as editor of Playboy 40 years ago, I'm bemused to see him, still in his trademark pajamas, popping Viagra and putting on a brave front even as the culture passes him by.

"This is one of the very best times of my life," he tells a New York Times reporter, whose reaction is "You want to believe him, but it is hard to ignore the realities of his business. Playboy Enterprises, hobbled by a shifting media landscape, is in need of heart paddles. On Tuesday, the magazine said it would cut the circulation numbers it guarantees to advertisers to 1.5 million, from 2.6 million. The company has lost money for seven quarters in a row."

In an era when nakedness is all over cable TV, Hef's Playmates and Bunnies are as retro as corsets and girdles, but the man who built an empire on daring to publish Marilyn Monroe's nude pictures in 1953 is in as much denial as the Gloria Swanson character in "Sunset Boulevard," waiting for Mr. DeMille to film the next closeup.

Nonetheless, with "three live-in girlfriends--each young enough to be his great-granddaughter," Hef is ready to go out in style as the crypt he bought next to Marilyn in a Los Angeles cemetery waits for him.

If there is an afterlife, it would be fascinating to overhear their conversations as she has "nothing on but the radio."

Another Heartbreak for Hugh Hefner

He is 82 now, but dating doesn't get any easier. The sad news today is that one of his latest live-in girlfriends is leaving after Hefner broke the news that he isn't planning to marry her or have children.

Holly Madison joins the long list of broken-hearted exes that the Playboy founder has led on only to falter when it came to vowing eternal fidelity.

Ms. Madison might have guessed the truth last year when Hefner sadly admitted he was not the father of Anna Nicole Smith's baby, a clue that his reproductive days might be coming to an end.

But the silver lining is that their business relationship goes on in a TV series, "The Girl Next Door," and that 19-year-old Playmate twins Karissa and Kristina Shannon are living in Hefner's mansion to console him.

His breakup with the 28-year-old Ms. Madison may have been foreshadowed half a century ago when an intended inamorata balked at entering a relationship by saying, "But I've never dated anyone over 30."

"Neither have I," Hefner assured her.