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Flashback: Inside the Playboy Mansion With Hugh Hefner

Since modern America has come to resemble nothing so much as the inside of the Playboy Mansion, it’s tempting to call Hugh Hefner a modern prophet.

This story was originally published in the August 30th, 2000 issue of Rolling Stone, U.S. edition.

He is not merely famous. He is fame. He is the most famous man, with the most famous house, in the most famous neighbourhood in the world. He has the most famous parties, with the most famous guests, and their fame is the source of his own. Because he is famous for his work, and he is famous for his women, but mostly, he is famous for his friends, that swirling swarm of spectacular celebrities who perpetually grace his grounds. He is famous for being immersed in them, for being saturated and inundated with their fame. He is famous, then, by social osmosis. Famous for being famous among the famous.

His house is nearly as famous as he is. So famous that it isn’t called “a house.” So famous that it isn’t even called “a mansion.” It is The Mansion, always with capital letters, always the definite article. It was The Mansion when it was first built, in the late 1950s, in Chicago, a brick manse on the Gold Coast. It was The Mansion in the early Seventies, when it moved to Los Angeles, a granite castle on rolling hills. And it will remain The Mansion, no matter where or when, because The Mansion is not a place. It is an idea, a graduation stage in the school of celebrity. To be invited there is the Hollywood proof of personage.

Which helps to explain why the task of choosing company is a delicate matter. With each name on the list, Hugh Hefner is giving a voucher, an assurance that his guest belongs in the company of the Jacks and the Warrens and the Clints. One wrong guest – say, Vanilla Ice – and his legendary status could diminish. So he must be attuned to the pomp and the sway of mainstream American tastes, but he also must be able to predict who will last beyond the moment.

For help, he has the tall and vigorous Mary O’Connor, 28 years at his side. Months ahead of any event, she is keeping a mental notebook: this one, yes. That one, maybe. The one who puked in Asia de Cuba, no way. Last year, she OK’d Billy Zane, and the year before that, Leo. This year, it’s sweet, young Thora Birch who receives the newcomer’s welcome. She can be spotted at his parties and his private movie screenings, even Easter Sunday morning, strolling through the grass, all green eyes and pout, as a flurry of children and Playmates scatter through the bushes in search of painted eggs, as butlers attend to the trays of toothpicked morsels, and as he, the host, sits upstairs alone, like so many times before, the only star unwilling to shine, hiding in his study, reading and writing and revising his life’s work, pleased to be far from the loathsome party he has brought upon himself.

Hugh Hefner at Playboy Mansion West. Hefner founded Playboy in 1953 and has since the expanded it into a multi-million dollar empire encorporating real estate, nightclubs and the sale of sundry products. Credit: M/K/Camera Press/Redux.

Forget everything you’ve ever read about Hugh Marston Hefner. Forget everything you’ve ever seen on television. Forget everything you’ve ever been told. Forget the elaborate story you’ve heard about his life, one too many times. Because I mean to tell you, in no uncertain terms, that everything you’ve heard is bullshit.

For the past 18 months, I’ve been studying the guy, mostly up close and personal. Where other reporters are usually granted no more than an hour’s interview, Hef made himself uniquely available to me, for reasons I don’t quite understand. He has reorganized his schedule to see me on short notice, and he’s never refused to answer a question. He’s let me visit him frequently, anytime I wanted. I’ve made dozens of trips through his vaunted halls, chatting with him, his friends and his employees. I’ve been to The Mansion to watch boxing matches, and I’ve been to his small private dinners. I’ve been there on days when Hef didn’t feel well. We’ve had long conversations about history, politics and religion. We’ve reclined on the sofa in his private den to discuss the role of PR in his life. I even watched him pick up a girl once, but I’ll get into that later.

Throughout all my reporting and all my inquiries into his past, Hef has asked for only one thing in return: that I differentiate myself from my colleagues. “Most reporters come to me with a preconceived agenda,” he told me after our first meeting. “They end up with a story that’s very superficial, without much insight to the man inside.”

I have tried, at his request, to do better than my peers. I’ve kept my eyes and my mind open for that man inside, and now, looking back, I can’t be sure whether Hef would have wanted me to find what I did. Because the man I found, lurking within those silk pajamas, is not the lecherous creep the media portray, but he’s also not the man that Hugh Hefner claims to be, the charming lothario king. The Hugh Hefner I found is more interesting than either, more bright, more cautious, more human. He’s fragile, romantic and full of ideals. He has given his life for a cause.

Before I met Hugh Hefner, I believed all the usual things about him – that he was suave and debonair, that he was a swinging bachelor, that his mere presence probably charged the air. After all, I grew up in the 1980s, a kind of Indian winter for the sexual revolution, part of a generation which, in the words of Hunter S. Thompson, was “taught that rain is poison and sex is death.” To me and my peers, Hefner represented the ultimate rejection of our culture’s sexual phobias and fears. Here was a guy who could lounge by the pool all day, sipping piña coladas and screwing strumpets.

Hugh Hefner working in bed, Chicago, 1973. Credit: Everett Collection.

Then, one day last year, I made my first trip to The Mansion. The Mansion I walked into held none of the epicurean delights I had heard about. No sooner had I passed through the front door than I was ushered by an employee into a small, wood-paneled room with a painting of Hefner on the wall and a backgammon board inlaid on the table. Nobody else was around; the place seemed improbably solemn. For a moment, I wondered if Hugh Hefner had died. And then he walked through the door, in black pajamas and a red smoking jacket, looking very much alive, albeit rather apprehensive.

“Well, hi there,” he stammered in a deep nasal voice, putting his hand out for a shake and giving a nervous grin. He ambled around to a sofa by the window and seated himself but instantly stood again. “Can I get you a Diet Pepsi?” he asked, his voice unsteady. I said yes, thank you, and he forced another smile, lurching toward a cabinet, fumbling around for a while, then returning with a small bottle, which he shoved toward me and then yanked back, going again to the cabinet and fumbling around some more. When he finally returned, he had come up with a small tumbler, but he had a look of great embarrassment as he explained that he didn’t have any ice.

We began to chat. Immediately, he launched into the official story, the one you hear on A&E’s Biography, the one he has told in almost every interview he has given since 1962. “I was raised in a conservative, repressive home,” he said. “I tried the traditional life, the life that was handed to me, and it didn’t make me happy,” he said. “Playboy was created as a response to my own puritan upbringing,” he said. “I found out that I could live my way. I’m living out my own fantasy,” he said.

After several hours, he excused himself and went upstairs for his daily bowl of soup. Somewhat baffled by his nervous behaviour, I headed out to the back lawn for some air. I was just starting to relax when out of the blue, I heard a thrashing sound behind me, and when I turned around, I saw Hugh Hefner sprinting across the grass, calling my name, carrying something large and red in his hands.

“Wil!” he shouted, catching up. “Ahh, yes,” he muttered. “I just, ahh, wanted, ahh …” The big red thing in his hands was a book titled Inside the Playboy Mansion. He thrust it toward me, wringing his hands, and mumbled, “I thought you’d, ahh, find this, ahh, useful.”

“Thanks,” I said, taking the book. I flipped open the cover and saw what he’d written on the first page: “For Wil Hilton, who shares the dreams. Best wishes, Hef.” As I stood there wondering what I might have said to prompt this intimate, if trite, inscription, Hef shirked off into his Mansion, robe flowing behind him, his silk pyjamas brushing the surface of the grass, gray hair poking up in all directions at once.

In order to understand Hef’s awkward behaviour, you have to understand the first 33 years of his life. Those are the years he often calls “repressive” and “unsatisfying.” In his version of the story, those are the years that led him to rebel against puritanism, to become a playboy lothario.

Hugh Hefner Senior Year 1944. Credit: Seth Poppel.

In truth, those years were nothing if not ordinary, and for the first half of his life, Hugh Hefner was thoroughly conventional. Born to an upper-middle-class Chicago family in 1926, and blessed with an above-genius IQ, his teen years were filled with the kind of gawky extracurricular activities you might expect from a future congressman. He participated in student government, acted with the drama club and organised school dances. At home, he was allowed all the normal accouterments of teen life. He hung magazine pinup girls on the walls of his bedroom, had parties in the basement, and his mother once caused a small scandal in the neighbourhood by giving him a book about sex.

“As a matter of fact, that’s a credit to my mother,” says Hef now, hedging a bit. “And in that sense, it was a nurturing environment. But there was no hugging or kissing.”

After graduating from high school with honors in 1944, Hugh (or Hef, as he had by then nicknamed himself) made the untitilating decision to enlist in the U.S. Army, where he spent two years on desk duty. After an honorable discharge in 1946, he hurried off to college, where he embraced the typical university cliches: pledging three fraternities, attending virtually every football game, majoring in psychology and remaining, until the age of 22, a virgin. By the time he graduated, Hef was engaged to his high-school sweetheart, and the two were promptly married, moving into a spare bedroom on the top floor of his parents’ house.

His approach to his career was equally conventional. After blundering through several odd jobs, he found work at Esquire magazine, writing direct-mail solicitations for the subscriptions department. By his own account, it was boring and tedious work, but also by his own account, he was satisfied and probably would have remained at Esquire for many years except that, in 1951, the magazine moved its offices to New York, leaving him behind. Married and unemployed at the age of 25, he tried his hand at cartooning for a while, and when that didn’t work out he took a job in the circulation department of a company called PDC, a publisher of gun journals and girlie magazines, which he described to a friend as “an outfit that specializes in nude photo magazines and other questionable enterprises.”

In 1952, the 26-year-old Hefner decided to start his own magazine. His wife was pregnant; it was time to start making some serious money. At first, he hoped to produce a wholesome journal about Chicago, but when he failed to procure financial backing for that idea, he considered starting a trade magazine for cartoonists, and when that didn’t catch on, he returned to the drawing board once more and, remembering the commercial success of PDC, ultimately decided that nude photo magazines weren’t so bad after all. Writing to one potential backer, he explained, “Sex is surefire, and the early issues [of my magazine] will include more than their share.” The backers agreed, and in 1953, with 6,000 borrowed dollars in hand, he began to sculpt the new magazine, initially calling it Stag Party and later changing the title to the more erudite Playboy.

The first issue of Playboy was disjointed and unoriginal. Hefner, short on cash, had culled most of the articles and photographs from other publications, and he had drawn most of the cartoons himself. In fact, the only thing memorable about that first issue was that it contained a long-forgotten calendar photo of Marilyn Monroe in the buff, which no other magazine had thought appropriate to publish. When the inaugural issue of Playboy hit newsstands in December 1953, it sold out. A second issue followed, then a third, and soon enough, Hefner’s “questionable enterprise” was putting food in the mouth of his first child, Christie.

Circa 1960s. Hugh Hefner who launched one of the most controversial magazines in publishing history, views photographs in his Chicago office. Credit: Bettman/Getty.

But even as Playboy earned a reputation for boldness and provocation, its editor remained, in the parlance of the times, a real square. While the magazine advocated a life of free-spirited adventure, sexual abandon and, above all else, good taste, Hugh Hefner’s lifestyle was the opposite. As editor and publisher and copy editor and page designer and cartoonist – to say nothing of being a new father – he had little time to live out the fantasies that Playboy described. Instead, he worked himself ragged. In his few hours of personal time each week, he would return home to his family, where he caught up on lost sleep.

“Those were very good years,” he reflects now. “Even though the magazine was being put together in an amateurish way, it was rewarding to work hard and see results.”

To Hefner, it was of no significance that his magazine did not reflect his own personal lifestyle or interests. What was important to him was that Playboy should depict a lifestyle that readers would want to emulate. He made this point clear in his first editor’s letter when he wrote, “Affairs of state will be out of our province. We don’t expect to solve any world problems or prove any great moral truths. If we are able to give the American male a few extra laughs and a little diversion from the anxieties of the Atomic Age, we’ll feel we’ve justified our existence.”

On my first night at The Mansion, after my awkward encounter with Hef on the lawn, I happened to hit it off with some regular guests, old friends of Hef, stars from 1960s television shows and their Playmate wives. On the invitation of some of these characters, I ended up hanging around The Mansion for a full week, sleeping during the day and partying at night. When I finally went home the next weekend, I could hardly take the deflation, and so, a month later, I went back for Hef’s birthday party, spending another week in his company. As the summer and fall and winter passed, I stayed in touch with Hef and his pals, saw them on my visits to Los Angeles and took them out clubbing when they came to New York.

But the more time I spent in Hef’s company, and the more I spoke with his friends, the more inexplicable he seemed. It became obvious to me that somewhere in the depths of his imagination, he was dissatisfied with the life he had created for himself. It haunted him, obviously, constantly. At one party, I watched him duck away from the crowd, then stand silently in an empty room, catching his breath and shaking his head, trying to muster some enthusiasm. On a quiet Friday night, I watched him assemble guests for a movie, then slip out to be alone. I noticed that he avoided certain celebrities, the ones with booming voices. In the middle of a midsize gathering, I saw him head upstairs to take a nap. And most surprisingly, I watched with amazement as the people at his side failed to notice. Here was a man clearly annoyed by his own party, yet nobody seemed to care.

On a few scattered occasions, some of his oldest friends spoke of the things I had noticed, but indirectly. One night, one of Hef’s closest friends confided, as we sat on the front lawn and smoked an enormous joint, “All his life, he’s been misunderstood. It drives him crazy.” Another evening, the actor John Phillip Law, from the sci-fi cult classic Barbarella, pulled me aside and confessed that Hef was the most moral man he’d ever met and that he didn’t use the word moral lightly. And on a third night, I sat on the rear terrace with a Playmate named Julie, talking about the future of The Mansion, about what would happen when Hef wasn’t around anymore, when suddenly she started to tear up. She looked behind us at The Mansion, out over the crowd and then, after glancing around, she seemed to slump. “You know,” she said, nodding knowingly and waving her hand toward the party, “there’s more to him than just all this.” I pretended to understand what she meant, but I didn’t understand. I couldn’t understand. I didn’t have the faintest clue how anyone could want more than “all this.”

Playboy bunny Sheila Levell (left), Playboy founder Hugh Hefner and Playboy bunny Holly Madison perform a scene during the filming of a commercial for ‘X Games IX’ at the Playboy Mansion on May 6th, 2003. Credit: Robert Mora/Getty.

Now then. The moment when Hugh Hefner became a playboy, when “all this” came to be. It was 1959, and he was 33 years old, still married, still dressing poorly, still toiling around the clock and still vaguely satisfied by it all. Playboy was just entering its seventh year, and the American public had begun a boisterous debate about what, exactly, the magazine stood for. Conservatives, in particular, dominated that discussion, frequently accusing the magazine of moral apathy and social destructiveness. In one article, the noted Amherst professor Benjamin DeMort described Playboy as “the whole man reduced to his private parts.” Others accused Hefner of objectifying women. Others claimed that the magazine was a communist plot. And still others likened Hefner to the devil.

Who wouldn’t be offended by allegations like these? Hugh Hefner certainly was. He had started the magazine as a business, yes, and in the beginning he had intended to be relatively amoral about its content. Not immoral, mind you, but amoral. He had gone into the project thinking that it would be wise to steer clear of politics and moralism, and to focus on entertaining his readers. And yet, as the magazine’s first half-decade passed, his internal moral compass had begun to tremble, and against his better business judgment, he had begun to sprinkle some politics on his pages. In 1957, he published “The Pious Pornographers,” a study of sexual stereotypes in mainstream journalism. In 1958, he published “Eros and Unreason in Detroit,” a look at the environmental damage caused by gas-guzzling cars. And in 1959, he published “The Cult of the Aged Leader,” a call for younger men to get involved in politics.

Yet, to his dismay, nobody seemed to notice. Here he was, making all this effort to turn Playboy into a magazine with a conscience, and nobody gave a damn. No matter what he published, whenever he sat down for an interview, he was asked, almost exclusively, about sex.

“I didn’t intend for Playboy to be a sex magazine,” Hefner says. “Playboy was intended to be an all-encompassing men’s magazine, and if you’re going to be a men’s magazine, how can you possibly not include the thing that men are most interested in, which is sex?”

“I didn’t intend for Playboy to be a sex magazine,” he now reflects, his voice pitched high in exasperation. “Playboy was intended to be an all-encompassing men’s magazine, and if you’re going to be a men’s magazine, how can you possibly not include the thing that men are most interested in, which is sex? You have to. What we tried to do was put sex in a context that also includes good writing and a conscience. For a lot of people, that was not so clear. It was obvious to me, but it wasn’t so obvious to other people.”

By the early 1960s, Hefner was frustrated. He wanted Playboy to be taken seriously, but he didn’t think it should come at the expense of the sexual content. To Hefner’s way of thinking, sex and ideas were two of the most exciting elements in life, and he didn’t think Playboy should have to choose one over the other. In fact, the more he thought about it, the more he realised that people are expected to make the same choice. In high school and college, as he remembered it, students were expected to identify themselves as either smart kids or popular kids, and the two labels were mutually exclusive.

At 33, Hugh Hefner was finally ready to start challenging the rules of society. He wanted to prove that sex and decency could go hand in hand that smart guys like sex, too. And he decided that the best way to prove that such a balance could be struck would be to strike that balance himself.

It was then that Hugh Hefner made the most important decision of his life: He decided to become his own mascot. No longer would he hide behind his desk, the invisible force behind Playboy. No longer would he settle for being the editor and the company president. From 1960 onward, he would set an example of the moral yet sexual man. He would, for the first time, become a public face, a man whose sexual life left nothing to be desired, and yet whose political idealism was fervent. He would hold orgies, but he would also hold fund-raisers for political candidates and for Jesse Jackson’s Operation Breadbasket. He would fight for civil rights, and he would fight for women’s rights, but he would also fight for sexual rights. He would fight for the end of nuclear proliferation, but he would also fight for the end of antisodomy laws.

In his imagination, Hefner began to refine his picture of this perfectly balanced man, whom he called “Mr. Playboy.” He decided that Mr. Playboy would be erudite and educated, as well as stylish and sophisticated. Mr. Playboy would be colorblind and would champion women’s sexual liberation, just as he championed men’s. Mr. Playboy would be so charming, and so irresistible that people would flock to him, and by being so popular, he would be heard.

Hugh Hefner Boss of the Playboy Empire arrives with an entourage of Bunny Girls at London Heathrow Airport on June 25th, 1966. Credit: Getty.

It was, in many ways, an age-old image, this Mr. Playboy ideal, modeled largely on the movie heroes that Hefner had worshipped as a kid. And yet, as familiar as the prototype of Mr. Playboy was to him, he knew that he was no Mr. Playboy. He didn’t dress well, he didn’t socialize well, he didn’t live a very exotic life. It was time to make some changes, he decided. Fast changes.

So in December 1959, Hugh Hefner began his metamorphosis. First, he took out a massive bank loan and purchased a multistory, red-brick-and-limestone palace on Chicago’s Gold Coast. Next, he put $1 million into renovations, building an indoor pool, a movie theater and the piece de resistance, an underwater bar, where guests could sip drinks while watching Playmates swim naked. He parked a convertible white Mercedes Benz in front of the house, along with a Mercedes limousine, complete with two orange flags bearing the rabbithead logo, and for his personal image, he purchased a red-velvet smoking jacket, which he thought would appear especially sophisticated if it were worn while smoking a hand-carved pipe, so he bought one of those, too.

To introduce Mr. Playboy to the public, Hefner financed his own television program, Playboy’s Penthouse, a cocktail-party-cum-variety-show with himself as host, featuring any number of celebrities as guests. Between humor segments and jazz and rock performances, Hef and the guests would sit down for discussions about civil rights, ecology and, of course, sexual repression. As Hefner explained to an interviewer in the 1970s, “The purpose of the show was to reach a broader audience and let them know what we were about and what Playboy was all about. … Hopefully they would begin to discover – those people who did not read Playboy – well, son of a gun, this guy isn’t a dirty old man.”

It may have been a good idea, but from the start Hugh Hefner was the wrong man to set his own example. Despite having the best intentions, he was, as he had always been, socially awkward, and if anything, his awkwardness was exaggerated on television, as he jerked about the set, clutching his pipe, failing to produce witty repartee with his guests and generally looking nervous. After seeing the first few shows, several of Hef’s friends suggested that he hire a professional actor to take his place, but he refused, and so the show remained, for the duration of its 26-week run, a parody of itself.

However, Hef was committed to his reinvention, and when Playboy’s Penthouse went off the air, he was determined to stay in the role of Mr. Playboy. He had put a small fortune into his new identity, and by the end of 1960, he had cloaked himself in the accessories of a bachelor socialite: He had taken up residence at The Mansion, he had spent well over $2 million on renovations, cars and clothing, and, on the surface, he had begun to look so much like a playboy, it was difficult to tell that he wasn’t one. “All the props were in place,” he says, in a rare moment of self-revelation. “I was prepared to start living the life promoted in the magazine.”

By day, the mansion is empty and sterile. With stone walls and Tudor thatching, a cavernous wood-panelled foyer, autumn-coloured furniture and plush rugs, the fabled castle has the feel not of a lavish playpen but an art director’s imitation of one. The marble countertops are almost too neat, the velvet-walled bathroom too spick-and-span. Even upstairs, in the semiprivate quarters where old friends sometimes crash, you’ll find crisp sheets and unblemished carpeting, perfectly matched (empty) dressers. It is possible that, beyond these rooms, in the truly unvisited quarters, Hef’s personal bedroom and his mysterious study, where nobody except himself and his girlfriends are allowed, one might just find an honest mess, some evidence of human error. But everything else has the air of stark comeliness, of immaculate, kempt constriction. Throughout the six-acre grounds, dozens of employees labor to maintain this delicate perfection: butlers, chefs and bartenders. Taken as a whole by the light of day, all this fastidiousness simmers with seriousness; it stews in its own flawless grandeur.

Hugh Hefner birthday party at the Playboy Mansion in 1998. Credit: REX.

And then comes night. The Mansion explodes. Transforms. Metamorphoses, just like Hugh Hefner. Limos line up at the gates. Disco music trickles through hallways. Gourmet delectables adorn every countertop. And the stars begin to arrive: Oscar de la Hoya, dancing with four Playmates at once; Jeff Goldblum leaning on the bar; Alyssa Milano and Shannen Doherty carousing on the back patio; Kevin Costner bopping his head off-rhythm; Tori Spelling and Claire Danes being civil to each other; Ice T waiting in line for the restroom; young actors stumbling, drunk, near the entrance to The Grotto. And if, by day, the stark environment feels like Hugh Hefner’s House, then by night, it is unmistakably Mr. Playboy’s Mansion, a place of fantasy and excess, of decadence and lawlessness. And most of the time, the only thing missing is Mr. Playboy himself.

One night at The Mansion, about a year ago, while all this madness was under way, I found myself hunkered over the backyard bar, sipping a gin and tonic, eyeballing Pamela Anderson’s reduced cup size and marveling at the blissful extent of my inebriation. I was ruined, juiced up on everything – a personal friend had sent me into the event with a high-power herb cookie; some girl had slipped me some blow; and Hef was supplying a bottomless source of booze. I had been chugging and puffing and dancing and skinny-dipping and stumbling around for hours, and as I stood by the bar, staring at the space where the eighth wonder of the world used to be, I couldn’t shake the sensation that, in the battle of the ages, the good guys had finally won.

From the corner of my eye, I saw Hef pattering by in his pj’s and tousled hair, and as I watched him inch his way through a cluster of chatty celebrities, I realized that he was coming over to me. A few moments later, he stood beside me at the bar, and through my blurry eyes, I could discern that he was smiling. “You’re the new Great Gatsby,” I heard myself say, and then I frowned, because I had no idea what I meant. But he didn’t seem offended, only sipped from his drink and told me that the comparison was often made. Just as he was speaking, a lithe young blonde sidled up next to him. I hadn’t seen her before, but I knew enough to know that she wasn’t one of his official girlfriends. Without so much as glancing at me, she slipped her arm around his waist and whispered something in his ear, and he grinned, then turned his head to whisper something back, and before I knew it, he was talking again to me, seeming to say goodbye.

“We’re going to head upstairs,” he said, raising his drink in a toast. And I nodded, suppressing a burp, visibly confused, and clumsily returned his toast. They began walking together toward the house, when suddenly Hef turned, and, with the young girl’s arm still around his waist, he looked over a few heads to me, giving a sheepish smile and saying loudly, in his ironic voice, “You know, I’m always looking for another stray lamb.” And with that, he disappeared.

Hef never came back downstairs that night, though the party continued until dawn. Maybe he got laid and then fell asleep, but I’d be willing to bet that it was something else. Because I’ve seen him sneak off from too many parties to think this one was an accident.

Like his parties, Hugh Hefner’s image has always been more of a public statement than a personal choice. His metamorphosis into Mr. Playboy in 1962, for all its PR value to the magazine, was never just a self-serving effort. It was also an attempt to change American ideas about sexuality, a way to challenge the stigma of sexual freedom. When Hef took on his role, blending his political rhetoric with a promiscuous lifestyle, he was trying to challenge the idea that casual sex was immoral. He wanted to prove that a moral man could be sexual, and that a sexual man could be moral.

“I was particularly concerned,” he says, “with the fact that we defined sexual morality in a completely different way than other types of morality. In any other area of human activity, morality is what is good for society. It’s different with sex. The ‘thou shalt nots’ reinforced the idea that sex is only for procreation, which is very hypocritical when you look at people’s natural sexual desires.”

His transformation into Mr. Playboy, however, only served as an introduction to his ideas. He had established himself as a model of his principles, but he also wanted to do more.

“I thought it was time to come out from behind the desk and live the life that I was promoting,” he says, “but at the same time, I also thought that it was time for me to sit down and spell out what I believe, which is that repression is a cancer, and when we repress our sexual instincts, we enter a world of denial and shame that undercuts the foundation of civilised society.”

His concerns about repression, denial and shame were supported by a landmark academic study by professor Alfred Kinsey at Indiana University. In the 1940s, Kinsey, a Harvard-educated zoologist, conducted the first major study of human sexuality, interviewing approximately 18,000 men and women about their sexual histories and publishing two volumes on his findings. The first volume, published in 1948, was called Sexual Behavior in the Human Male and was a shocking revelation at that time, because it revealed that most men and women enjoyed, in private, sexual behaviours which they felt compelled to deny in public. Specifically, the first Kinsey Report found that 92 percent of men masturbate, 85 percent of men have premarital sex, 69 percent of men have had sex with a prostitute, and 50 percent of married men have had extramarital affairs. But in virtually all cases, the subjects were quick to scorn anyone, including themselves, who engaged in those behaviors.

The second Kinsey Report, titled Sexual Behavior in the Human Female, found similar levels of hypocrisy among women, including the discoveries that women who have premarital sex are able to orgasm more often and that a surprisingly high number of women have engaged, at least once, in a lesbian affair.

To Hugh Hefner, a psychology major, these findings could mean only one thing: that Americans were living in an unnecessary state of self-denial and self-rejection. He was convinced that society would suffer for as long as we repressed our sexual instincts. And while he felt that it was useful for a role model like himself to live a sexually unencumbered lifestyle, he wasn’t satisfied merely to set an example. He wanted to write down his theories and present them to the world.

Towards the end of 1962, Hefner put pen to paper and began to write his own manifesto on human sexuality. What evolved over the period between December 1962 and May 1965, in 22 issues of the magazine, would be titled “The Playboy Philosophy,” and it would draw on more than 3,000 years of political, social and philosophic theory. When I say that “The Playboy Philosophy” is a broad and far-reaching manifesto, I mean that it is insanely, absurdly, painfully thorough, a compilation of nearly every thought ever recorded on the nature of sexuality.

“The original notion was to simply write a piece in the anniversary issue,” he says now. He pauses, chuckles and adds, “I am nothing if not obsessive.”

True enough. From the start, writing “The Playboy Philosophy” virtually absorbed Hugh Hefner’s life. He retreated into a windowless private office deep inside the Chicago mansion and, even as parties raged below, remained isolated there, fueling himself with prescription amphetamines and furiously writing hundreds of thousands of words. According to his biographer Frank Brady, during the two-and-a-half-year period that he spent writing “The Playboy Philosophy,” Hefner left The Mansion a total of nine times. He would write for several days on end, then sleep for eight to ten hours, wake up and resume his work.

Publisher Hugh Hefner looks over proof sheets for ‘Playboy’ magazine in Chicago. Credit: AP/REX/Shutterstock.

In the first seven instalments of his “Philosophy,” Hefner laid down his premises. Under headings like Caesar and God, Darwin and Prohibition, Obscenity and the Law, and Justice Black and the Constitution, he argued that the foundation of American capitalism lies in the self-determination of the individual. Free men, he wrote, can be expected – and should be encouraged – to pursue their own dreams. Without dreams, Hefner argued, the human spirit will dampen, and we will lose the ingenuity and enthusiasm that have made America what it is. In Hefner’s view, if human fantasies were the good guys, then the bad guys were religion. “Much of the dogma still remaining in today’s organised religion tends to de-emphasise competition and the importance of the individual,” he wrote. “A sort of selfless interest in helping others, without doing anything to help oneself, is stressed, with more attention often given to man’s inherent weaknesses than his strengths.”

In the next five instalments, he began to examine the history of religious influence on sexual mores, beginning with sex in early Judaism and citing Deuteronomy; continuing through the Middle Ages, citing Pope Innocent VIII; on through the Renaissance and Reformation, citing John Calvin and Michael Servetus; into the Victorian era, citing Lord Acton and E.S. Turner; and finally making his way to present-day American sexual attitudes, citing, of course, Alfred Kinsey.

“Modern American morality,” Hefner wrote, “is an amalgamation of the superstitious paganism and masochistic asceticism of early Christianity; the sexual anxieties, feelings of guilt and shame, witch-hunting sadism and sex repression of the medieval church; the desexualised courtly love of the troubadours; England’s Romantic Age, wherein love was presumed to conquer all; and the prohibitively strict, severe, joyless, authoritarian, unresponsive, book-banning, pleasure-baiting dogma of Calvinist Protestantism, Puritanism and Victorianism.”

By the beginning of 1964, he had undertaken a comprehensive study of sexual law in the 50 states, emphasising that much of the law regarding sexual behaviour was rooted in religious doctrine. Citing Morris Plascowe, a professor of law at New York University who specialised in sexual ordinances, Hefner wrote, “Sin and crime are not synonymous,” adding, “By making marriage a church-state license to enjoy the pleasures of sex – by making sex outside of marriage a social and legal taboo – our society supplies a tremendous impetus to early marriage, whether couples are emotionally, psychologically and economically prepared for it or not.” And in a section titled Contemporary Antisexualism, he wrote, “The mere expression of an unpopular opinion on the subject [of sex] can still cause the dismissal of a college professor (as it did at the University of Illinois in 1960); or a too-realistic, though award-laden, drama by Eugene O’Neill may bring down the wrath of a university president and prompt the resignation of the head and staff of an entire drama department (as occurred at Baylor in 1963).”

In summation, Hefner’s theory was this: American ideals and American progress will be hampered if we feel shame about our sexual instincts. He argued that, according to the individualist and capitalist underpinnings of our society, a man should be free to pursue his own fantasies, including sexual fantasies, so that he will be driven to innovate and produce. Sex, Hefner argued, goes along with money and power as the motivation for men and women to achieve. If people are deprived of the opportunity to fulfil those fantasies, then their freedom is being cut short, and their ambitions will dwindle.

In a perfect society, Hefner further argued, it would be irrelevant if the divorce rate increased, because the institution of marriage would no longer be sacrosanct. It would be immaterial if a person had sex with multiple partners, because sexual preferences would be treated as a personal matter. Furthermore, Hefner argued, in a perfect society, sexual behaviour would be so unfettered and so unimpugned as to be rendered insignificant, allowing men and women to proceed with their lives, expressing their ideas through their work without the unnecessary hindrance of shame.

“The great myth about sex and sexual instincts was always that if you bottled it up, it would go away,” he says. “The truth is, if you let those instincts out, they won’t haunt you anymore.”

If most americans haven’t ever heard of “The Playboy Philosophy,” it’s no wonder. You can’t find a copy in the bookstore, you can’t order it from Amazon.com. You can try to call Playboy headquarters in Chicago, but they’re running low on copies, and they’re saving what few they have.

After weeks of searching, I finally found a copy of the “Philosophy” on the Internet, and after sending a check for $150 to a random address on a Web page, I was pleasantly surprised when a small package arrived in the mail one afternoon. What I found inside wasn’t the glossy hardcover tome I was expecting but a shoddy grouping of four stapled pamphlets, each containing mostly text. Those pamphlets were printed in 1965, nine years before I was born, and represent the only time that the “Philosophy” papers have been reprinted.

And yet, whether or not modern America is familiar with “The Playboy Philosophy,” I would suggest that this manifesto contains ideas that have become, since their publication, universally familiar and popularly accepted in our culture. We Americans, still basking in the afterglow of the sexual revolution, have not only come to terms with most of our sexual instincts; we have, for the most part, embraced them. For better or for worse, premarital sex is no longer a taboo in most corners of the nation; homosexuality is rapidly becoming mainstream (despite the last phobic vanguard of the Boy Scouts); the act of menage a trois may not be commonplace, but it has clearly entered the lexicon of acceptable behaviour, appearing in movies and on TV without public outcry; and, perhaps most tellingly, America’s high divorce rate might reflect, for the first time, the actual level of dissatisfaction that many married couples experience. These days, if you want out of a marriage, the church and the state cannot easily keep you in it.

When Hugh Hefner dies, there will be a party, of course, and a thousand of Hef’s closest friends will convene at The Mansion, decked out in black for the last chance to raise hell in paradise.

Since all of these developments were described in “The Playboy Philosophy” some 35 years ago, and since the face of modern America has come to resemble nothing so much as the inside of the Playboy Mansion, it’s tempting to call Hugh Hefner a modern prophet. But even if he is one – even if he did predict our cultural course – it’s interesting to point out that he doesn’t know it yet. Even after 40 years of inhabiting his Mr. Playboy bodysuit, the fame is overwhelmingly irksome to him, and he spends most of his time locked away in the private rooms of The Mansion, reading and writing and continuing to study social theory. On the few occasions when he does come out to talk politics with his friends, he tends to sound like an echo, still railing against the American puritanism that he destroyed so long ago.

When Hugh Hefner dies, there will be a party, of course, and a thousand of Hef’s closest friends will convene at The Mansion, decked out in black for the last chance to raise hell in paradise.

Jack Nicholson will be there, wrapped up in Armani, and Warren Beatty will be wrapped up in Annette. George Clooney will bring a Playmate as his date; Bill Maher will probably bring three. Jon Lovitz will hang out at the backyard bar with Dan Aykroyd and David Spade. Kato Kaelin will be there, red-faced and flouncy, balancing a tray of bonbons, weaving through the mob of polk-a-dotted ladies, sashaying to the swollen disco. “Weird Al” Yankovic will wear a nightshirt and sunglasses, looking awkward and smiling a lot. Those of the Stones who are still able to stand will be standing, until they fall down. Young actors will be smoking weed on the back patio. Kareem Abdul-Jabbar will be hovering near the top of the party tent, looming over the crowd like an embarrassed college president chaperoning a fraternity bash.

The madness will throb, will spiral, will ache, as it has for twenty-five years, and The Mansion will seem to float above the fray like the House of Usher revived. And after a while, someone will take to the stage for an effusive, meandering speech, something like, “We’ll miss him a lot, but the important thing is that, even dead, he’s such a great host!” And the few who are listening will let out a whoop while the party rages on.

There will be gallons of free booze, as always, and sex in The Grotto at three. There will be a nine-screen wall of gigantic TVs playing footage of past bashes, and after a while, Hef will come onscreen, quite literally larger than life, smirking and mumbling things philosophic, things nobody will be able to hear. Things like, “I grew up in a family of puritan dogma, and I’ve been rebelling against it my whole life. We live in a society of sexual repression, a world of puritan blab blab blah.”

And he’ll be wrong, of course, as he has been for years, because the new world is nothing like that. Because the battle is over and Hefner has won. Because The Mansion has conquered the Earth. Because he gave up control over his personal life in order to give us control over ours. Because we live in his image and follow his Philosophy, whether he knows it – or we know it – or not.