Brilliant careers: Hugh Hefner, the indefatigable swinger

The 20th century's indefatigable swinger mixed martinis, cavorted women, and reinvented himself right up to the end

Published December 28, 1999 5:00PM (EST)

 (AP Photo, File)
(AP Photo, File)

Editor's note: Playboy founder Hugh Hefner passed away today, September 27, 2017, at the age of 91. In reflecting on his oft-complicated social and political legacy, we present, unadulterated, Chris Colin's thoughtful retrospective on Hefner originally published in Salon in 1999.

Hugh Hefner is probably having sex right now. Is it a leap to say so? No, because 1) Hef likes a good leap and 2) he really, really likes sex.

In considering Hefner's life, it's best to begin with a snapshot of the present: A short, gray 73-year-old man being pawed in a Beverly Hills mansion by four nude or semi-nude models. The mansion has monkeys and peacocks in its lavish gardens. Two of the four models are twins. The man is smiling. A lot. In the background, radiating outward: a country's worth of smaller homes, with fewer pawing models, less wildlife and the rest of us asking: How does he do it?

With Viagra, of course, and millions of dollars. Any man in possession of these things could be in the same snapshot. Indeed, when a chuckling Geraldo Rivera asked the Playboy editor, "Hef, how do you do it?" it reeked of manufactured naiveti. But Geraldo's gosh golly-ism about wealth and power belies a deeper mystery: What is it about Hugh Hefner that ushered him through standard American tropes -- mediocrity, lust, ostentation -- to the degree of veneration he's now wallowing in?

Part of it is his sense of romance -- Hefner talks passionately about "the male-female connection." And yet it's a funny idea of romance. From the outset, man's mark was often discernable in Playboy's photos -- a football pennant on the wall, a cigar burning in an ashtray near the frame -- but it was the female side of the male-female connection that got all the play. The naked female side, to be precise.

Still, the adolescent reverence for women's bodies bespoke a version of romance -- albeit puerile, underfed -- that other skin magazines lacked. Whatever Hefner believed respect for the fairer sex actually entailed, it was a respect he held at the core of his company's enterprises. When the '70s exploded with Playboy imitators -- Penthouse, Hustler -- Hefner responded with a newfound restraint. The "pubic wars" raged briefly (raising the bar on just how much skin could be found at the local newsstand), but Playboy dangled a seldom-seen white flag; there are limits, Hef decided, to what a classy rag like Playboy will show.

His chivalrous gesture marked a turning point for the magazine, or perhaps for the culture that now seemed to be eclipsing it. Two decades later, Hefner's creation reads not as radical, but as a monument to what radical once was.

Radical and huge: In 1971, when Playboy Enterprises went public, the world was buying seven million copies of the magazine a month. Twenty-three Playboy clubs took the Playboy philosophy and served it with drinks. A shrewd marketing strategy had transformed the Bunny icon from a dopey adolescent idea (rabbits, see, they like sex -- lots of it) to an immediately recognizable symbol of sophistication and style. Hefner, feeling philosophically obligated to embody the full playboy lifestyle, hosted a regular TV show that dripped v-neck sweater swank while spotlighting the best new acts.

Before the millions, before the publishing empire, before the first Playboy -- before what Tom Wolfe called "one-handed magazines" were ever held in one hand at all -- an 8-year-old Hugh Marston Hefner opened his mansion. It wasn't, technically, a mansion back then -- more of a small Chicago home, sans Bunnies. But it was the neighborhood hotspot, and if there was fun to be had, it was had at Hefner's. His career would later make bank on the girl next door's curves, but his life has always been about hosting.

Hefner's seamless host persona allowed him to usher 20th-century America through some of its most dramatic changes. Boilerplate histories brusquely credit him with the sexual revolution and move on. In truth, the various and complex liberations that fall under this rubric (credit for which Hefner always splits with sex-science pioneer Alfred Kinsey) represent just a fraction of his influence. Hefner's impact on notions of domesticity and single life, on male and female identity, on fashion, on publishing, on corporate branding wisdom -- even on our understanding of the postal system -- his impact on all of these are abundantly evident.

But first, a lurid magazine about sex. In 1953, creating Playboy was scarcely a stretch for Hefner: In high school he'd written an essay criticizing the lack of frank discussion about sex in America, and in his college newspaper he'd praised the recently released and controversial "Sexual Behavior in the Human Male," aka the Kinsey Report. The real stretch was for the rest of the country. Never before had nude pictures been successfully sent through the mail as a mainstream commercial venture. Indeed, the Marilyn Monroe photos, which appeared in Playboy's first issue, had existed long before Hefner got his hands on them, but nobody had dared challenge the powerful U.S. Post Office and its anti-obscenity regulations. Hefner went ahead with his plans, visiting newsstands throughout Chicago on the day the magazine went on sale, to monitor progress. Fifty thousand issues sold nationwide -- more than he ever thought possible.

In the '90s, Hef borders on kitsch; in the '50s, he was deeply radical. Looking back from an age of Jerry Springer and Hairy Butts magazine, it's hard to imagine a historical moment when two exposed breasts could ignite a revolution. America has quietly rewritten an entire era of dangerously repressive Puritanism into the occasional parody of Donna Reed suburbia and a few movies about McCarthyism.

In retrospect, the '50s seem to have been begging for an outlet like Playboy -- either to focus its repressive prescripts, or to have a little fun. And Hefner answered the call: He worked all hours, dutifully attending photo shoots with beautiful naked women and gradually mining the unexplored realm of swinging life.

If there's anything unfortunate about Playboy's naked ladies -- besides (depending on your point of view) their objectification or their idealization -- it's the way they obscure the authentically revolutionary impact of the publication: Playboy brought men indoors. It made it OK for boys to stay inside and play. Where other men's magazines -- Argosy, Field & Stream, True -- affirmed their readers' places in duck blinds and trout streams, Hef's took men inside to mix drinks, sit by the fire and play backgammon or neck with a girlfriend. In what would later become an ironic collusion with feminists such as Betty Friedan, Playboy critiqued the staid institutions of marriage, domesticity and suburban family life.

Suddenly bachelorhood was a choice, one decorated with intelligent drinks, hi-fis and an urbane apartment that put white picket fences to shame. Sophistication had become a viable option for men: The Playboy universe encouraged appreciation of "the finer things" -- literature, a good pipe, a cashmere pullover, a beautiful lady. America was seeing the advent of the urban single male who, lest his subversive departure from domestic norms suggest homosexuality, was now enjoying new photos of nude women every month.

The popular new male pastime came with an equally startling new wardrobe. If, as his own legend has it, Hefner liberated the human body, he did so in part by fitting it with nicer duds. Men once confined to drab grays and browns could now luxuriate in bold new styles. Appreciation for fashion, Hefner decreed, need not reside strictly in the female. The men's style magazines that now clutter newsstands have Playboy to thank for making elegant threads suitably masculine. Sensual fabrics and the body-accentuating designs that are now commonplace in even the most middlebrow of men's stores were virtually unheard of when Playboy first hit newsstands.

Not surprisingly, Playboy attracted more and more attention and controversy -- and Hefner happily stepped into the lightning-rod position. For the camp that considered him a pervert, it was impossible not to speculate about the roots of his perversion. Much was said -- and continues to be said -- about his strict upbringing. Hefner himself, well-versed in the art of biography-ready self-deconstruction, has remarked, "I was a very idealistic, very romantic kid in a very typically Midwestern Methodist repressed home. There was no show of affection of any kind, and I escaped to dreams and fantasies produced, by and large, by the music and the movies of the '30s."

Indeed, Hefner seems to have belonged to that segment of the population raised down the street at the movie theater. But this does not account for Playboy magazine. Perhaps more revealing is a story that got less airtime: Despite the family's rigid values, Grace Hefner once gave her young son an educational and rather forthright book about sex. "Gave" is misleading: she left it within reach and never said a word about it. In the 1930s, even this level of openness about sex in a middle-class home was rare. It's hard not to find something telling in the gesture. At once progressive and strangely conservative, it suggests the relationship Hefner would later develop with sex itself: He became a radical reformer who never quite lost his old-fashioned romantic values.

The romantic values were sometimes hard-won. At 16, Hefner suffered a crushing, if somewhat propitious, indignity. Already a misfit in his staid Chicago high school, the artistic, ambitious and bright student now found himself rejected by the girl he adored. He considered his ennui one last time and reinvented himself head to toe: Hef, he would be called from that day on, and as Hef, he would never again have to know failure.

The reborn Hefner spent his last two years of high school in a whirl of charisma, charm and popularity. During the day, he devoted himself to friends and at night, to his passion for cartooning. If it happened to Hef, it happened to "Hef," the cartoon character whose every adventure he chronicled with zeal, if not skill, in a strip, which was occasionally published in the school paper, other times simply handed around to friends. By the end of high school, 1944, he'd fallen in love again -- this time reciprocated -- and rushed off to the Army to serve as an infantry clerk.

Army life was miserable for Hefner, as he told his love Millie Williams in frequent letters. When he was discharged two years later -- he'd been stationed at a typewriter stateside for the duration of his service -- he returned to Williams with only the vaguest plans of cartooning for a living.

Hefner enrolled at the University of Illinois. As editor of the school's humor magazine, he started a feature called Coed of the Month. In 1949, he graduated, -- he'd doubled up on classes and finished in two and a half years -- took a job at Esquire magazine and married Millie (mother of Christie, Playboy's CEO).

Hef soon found that the American dream, at least as it was being dreamt in the early '50s, didn't work for him. The routine, the job -- and later the wife -- all felt constraining for Hefner. He left Esquire and went to work designing his magazine. Stag, as it was to be called, grew out of what Hef called a mature appreciation of the human body. The human body in question belonged to a young Marilyn Monroe -- Hef had gotten hold of never-published photos of the budding star with "nothing on but the radio." Changing the publication's name to Playboy, he borrowed money from his mother (she always wanted him to become a missionary) and took loans out on his furniture. He sat down at the kitchen table and did the first layout of the magazine himself.

"Playboy isn't like the downscale, male-bonding, beer-swilling phenomena that is being promoted now by some men's magazines," Hefner explained recently. "My whole notion was the romantic connection between male and female."

Playboy quickly became far more than porn, even if the depth was lost on some fans. With his deep new pockets, Hefner was soon bringing in America's best writers and pundits, in case anyone was reading it for the articles. Lenny Bruce, John Updike, Jack Kerouac and others were nurtured. And Alex Haley got his groundbreaking "Autobiography of Malcolm X" off the ground through his interview with the leader in Playboy.

Hefner worked to encourage his cultural revolution on other fronts as well. The Playboy Foundation, since its inception in 1965, has given away over $11 million in the name of social change. A devoted civil rights activist, Hefner funded assorted social action projects long before social action was hip.

Of course, the Foundation was scarcely enough to dissuade censure. As a testament to Playboy's unique cultural situation, the magazine received, and receives, criticism from all sides. The conservative group Concerned Women for America claims Playboy "belittled marriage" and "made commitment a dirty word." On the left, critics argue a similar point. And Naomi Wolf recently wrote, "A lot of men stay unmarried decade after decade because they bought the Hugh Hefner line that polygamist bachelorhood is ideal, and they lead largely empty lives."

But Playboy also sought to help feminism, at least in terms of articulating its various divisions. As the women's movement grew too massive and complex for any kind of heterodoxy, Hefner occasionally found himself marking assorted forks in the road. After Gloria Steinem went undercover as a Playboy Bunny in 1963 and published a scathing critique of the magazine's degradation of women, thousands of women -- many of whom made a living from various porn-related careers -- responded with equal venom. That which Steinem called degrading, they said, was the very thing that granted them a level of economic and sexual freedom that few women had previously experienced.

Hef certainly doesn't hold a monopoly on these watershed cultural moments. But a figure need not be responsible for brilliant history in order to play a brilliant role in it. Even if Hefner were nothing more than a lucky dope who accidentally stumbled upon cultural fault lines throughout his life, he is still genius enough to stumble upon them over and over.

Hef is happy. It's an overwhelming happiness, one so insistent that the darker periods of his life -- his divorce from Millie, his second divorce in 1989 from Kimberly Conrad -- get strangely clouded by light. The familiar elements of his biography come in shades of pink, so to speak, and his biographers generally seem charmed by all the mirth. This is where Hefner gets interesting. Instrumental to his success is not just an impressive publishing instinct, but an unparalleled knack for spinning myth.

It's not coincidence that Playboy is a household name -- more so than other publications with comparable sales. The magazine has woven itself into American mythology, elbowed its way onto the landscapes of growing up, of being a man. The archetypal coming-of-age narrative is nothing without that first flustered glimpse of a centerfold in the 7-11 parking lot. An uncanny ability to tap into the country's Zeitgeist has made Playboy as American as an apple pie sitting on a Thanksgiving table in a Norman Rockwell painting.

Even the Playboy Foundation feeds a certain brilliant fiction. As a part of its impressive good-deeds program, the foundation sets aside grant money each year for a handful of citizens whom it deems protectors of the First Amendment. As a result, patriotic has now been added to the list of attributes conflated with Playboy. The point is not that Hefner's mythologies are untrue -- often they reflect entirely accurate numbers, opinions and phenomena. Their cultural play takes shape in the way they are disseminated, true or not.

The myth doesn't stop with the company. Hef himself has gotten generations to acknowledge his charm, to revere his lifestyle and even to call him by his high school nickname. He's successfully transfigured himself from a man into a cultural icon. His silk pajamas, his Diet Pepsi at breakfast, his insistence on working from bed -- these constitute a folklore few can generate. A species of rabbit even hops around in the man's honor: Sylviligus palustris hefneri.

Bottom line, the guy's likable. It's a likability inextricably linked to his controversy, the kind that can only accompany 47 years of monthly nude centerfolds; we like him in spite of himself. Something in his air, or perhaps in the utter ridiculousness of a lifelong obsession with sex, begs forgiveness. His friendly smile, his candor, his unselfconscious cheer -- these put him in a separate league from the strident, post-lapsarian Larry Flynt types. Whatever moral criticisms we have, Hef convinces us to also enjoy his persona. Like any great creator of characters, he imbued his with both flaw and humanity.

It's an act, of course. Hefner has manufactured himself, his life, his mystique and our reverence. Long ago he created a swinging bachelor that would stir the world's imagination, then did the same with a married one. Now he's put his finger on that place in America's heart for the unapologetic old horn-dog. He has tapped into the country's need to at once adore and chuckle at a rejuvenated firebrand, to relive and rejigger a relationship it began nearly half a century ago.

Hef manufactured all this, and he'd be the first to admit it. With a Dickensian grasp of archetypes, he made a career of cooking up characters the world would love, or love to hate. From that first reinvention of himself in high school, the birth of "Hef," he's always extolled the benefits of a good makeover. And it's this kind of honesty that tends to anticipate and occasionally ward off criticism. During a recent radio interview, when "Fresh Air's" Terry Gross read him something of a riot act, it rang superfluous: Hefner has always been the first to admit his limitations, his flaws, his naked-lady obsessions.

And now Hefner's back. Having recently ended his famous decade of domesticity (Kimberly Conrad still lives next door with their two children) Hef has again invented himself as America's favorite bachelor. Hollywood again comes to parties at his mansion, and the floaty toys that had temporarily clogged the steamy grotto out back have made way for bathing beauties. An unabashed proponent of Viagra, Hef is doing his best Peter Pan act these days. And he's doing it with Mandy, Brandy, Sandy and Jessica.

If America's fascination with Hefner has indeed been rekindled as he claims, this rekindling is not so concerned with accuracy. In the great Playboy tradition, the icon has been airbrushed. The Hef we get is the swinger, the bachelor, the tycoon, the eccentric. He's the guy who always gets the girl, and she's the girl next door who just happens to have a killer bod and a deep commitment to sexual adventure. With Hef we get the apparel of the man -- the lounging, the martinis, the sex -- but not the man himself, and in this case, the man is actually interesting.

A new release from Grove Press sends the point home. Written by longtime Playboy columnist James Petersen and edited by Hefner, "The Century of Sex: Playboy's History of the Sexual Revolution, 1900-1999" chronicles America's relationship with sex over the last 100 years. More than that, it testifies to what is perhaps Hefner's greatest gift to his country: an impressive understanding of how sex has shaped 20th century America, and a commitment to share it. "Sex is the primary motivating factor in the course of human history," Hef writes in the book's foreword, "and in the twentieth century it has emerged from the taboos and controversy that have surrounded it throughout the ages to claim its rightful place in society."

The rightful part will always be up for debate. Hef is just happy there's a debate -- and that he's got four young naked women beside him to witness it.

By Chris Colin

Chris Colin is the author most recently of "Blindsight," published by the Atavist.

MORE FROM Chris Colin

Related Topics ------------------------------------------

Cultural Criticism Geraldo Rivera Hugh Hefner Playboy Retrospectives Sex Viagra