Hugh Hefner: The Playboy Interview

Hugh Hefner Lede Portrait - P 2011
Joe Pugliese

Hugh Hefner Lede Portrait - P 2011

Now 85, America's greatest buster of sexual taboos bought back his empire in March and has a new TV show awash in controversy (if not yet ratings). But after two marriages, a fiancee who ditched him, and hundreds of girlfriends, the self-described romantic says the one thing he's never found is his "ultimate soul mate."

On July 26, Hugh Hefner's sex life went viral. In a remarkable interview with Howard Stern, Hefner's ex-fiancee Crystal Harris, 25, who had publicly called off their wedding just five days before the event, flayed him alive, alleging they'd had intercourse just once and for the briefest of moments.

"I was drinking," she said. "It was, 'Whatever, why not try it out?' He's had so much sex, he's kind of over it. [It lasted] two seconds. It was an out-of-body experience."

Sitting in a rather Victorian den in his five-and-a-half-acre Holmby Hills, Calif., estate on a dazzling day in late August, dressed in his trademark silk pajamas and smoking jacket, Hefner seems more bemused than bitter about her account. He leans forward on a striped couch, hands between his knees, slightly frail, dwarfed by the height of the room.

His hair is thinning and he's a little hard of hearing, but in his ninth decade he's fully alert and a long way from the dribbling dolt of some recent reports -- among them an article that described him "[ripping] the kind of fart that one does not even attempt to hide," as if not quite in control of his body, let alone his mind.

Are the stories true or false?

"False," he says.

Did you have an active sex life?

"We had sex once a week. We had sex with her and a girlfriend. We had sex the first night that we met, with another girl, and it was such a nice relationship that I kept them both over for a weekend."

Does sex still interest you?

"Yeah, sure."

And you still have the same sex drive as before?


He shrugs it off, unfazed. Only later does it strike this reporter how bizarre it is to be asking an 85-year-old about his libido. But that's what happens when one builds an empire, life and reputation based on the most primal of human instincts: sex.


Whatever people think of Hefner's role in history, he's a man of enormous complexity: a breaker of sexual taboos who remains oddly traditional in his habits; a self-described romantic who hasn't found true romance; a brilliant, even cerebral editor who's surrounded himself with bimbos; the resident of a sybaritic pleasure-dome whose own greatest pleasures appear to involve backgammon and old Hollywood movies.

He remains an enigma to the world and quite possibly to himself, having spent more than a decade working on his memoirs before abandoning them altogether, preferring to let an outsider, Steven Watts, write the hagiographic Mr. Playboy: Hugh Hefner and the American Dream.

After seeing his reputation battered over the years by attacks from the left and right before staging a comeback with E!'s The Girls Next Door, he again, impressively, has found himself at the center of a pop culture moment. On Sept. 19, NBC debuted The Playboy Club, a lavish drama centered on the real-life Chicago hangout that opened Feb. 29, 1960, and became a mecca for anyone who was anyone.

The premiere of Playboy Club ranked third in its time slot, with 5 million viewers and a 1.6 rating in the 18-to-49 demo.

The series, a 21st century homage to a man whose influence began deep in the 20th, has sparked almost as much interest and, at times, bile as Hefner himself. The Hollywood Reporter's critic Tim Goodman wrote that "the whole thing quickly becomes hokey and a grind"; watchdog groups have slammed it -- the Parents Television Council is urging members to contact advertisers such as Chrysler and Unilever to call them out for supporting it; and NBC's Utah affiliate KSL-TV has boycotted the show.

All this despite NBC's ill-fated attempt at the Television Critics Association gathering in August to pitch the program as empowering to women -- just as Playboy has pitched itself, with limited success for decades.

Hefner himself scorns many feminist attacks. "The women's movement got hijacked to some extent with this antisexual thing," he argues.

The series, which stars Eddie Cibrian as a top attorney and Amber Heard as a bunny who accidentally kills a mafioso, was produced with Brian Grazer and Ron Howard's Imagine Entertainment and, Hefner says, initially sprang from Imagine's plans to film his life story.

"They went through some very strange permutations where, at one point, they were talking about it as a musical," he recalls. "But I felt that got in the way of the real story, which is more interesting."

Grazer still wants to make a biopic, but says the main problem has been locating "a central conflict in a charmed life. He's one of the most influential people [in our society], but finding that conflict is hard."

As to the series, Dick Rosenzweig, executive vp of Playboy Enterprises Inc. (PEI), says it came to NBC as an idea about "the first Playboy Club and some women growing up as bunnies -- a sort of Sex and the City and very cute, but not a drama." Producer Chad Hodge was hired to take it in a more serious direction.

With Playboy contractually protected from being shown in a negative light, the result almost certainly will burnish the image of one of the most controversial figures of the past 60 years. And it couldn't come at a better time.

Under Scott Flanders, who was named CEO in June 2009 -- effectively replacing Hefner's daughter, Christie -- PEI is going through the most radical shift in its history, spinning off its hardcore pornography assets, putting most operating procedures in the hands of outsiders and concentrating on maximizing its world-famous brand.

"We've been migrating away from being a global, diversified media company toward a brand-management strategy," Flanders says. Other than the magazine itself, "Playboy will now be a licensing company."

In August, PEI struck a deal with Manwin, a provider of online adult entertainment, to run and eventually own Playboy's hardcore Spice Networks, along with its digital subscription business. Manwin also will operate Playboy TV (formerly the Playboy Channel, whose programming ranges from reality shows to sex-themed films) but won't own it.

Similarly, Playboy has licensed the rights to five clubs -- one to launch in Chicago next year, joining others in London, Macao, Cancun and Las Vegas. It is also pulling back rights to its bunny logo, which has been spread thin across numerous products. Indeed, an April 2010 article in The Wall Street Journal criticized the company for turning "its bunny loose … slapping its famous logo on a tanning spray, a disposable lighter, a mattress, a couch and a line of drinks designed to boost the libido."

Hefner has had limited involvement in all this, noting, "The business end of business has never interested me."

What's left is an in-house film and television division, Alta Loma Entertainment, which will continue to work on projects like Playboy Club, possible Broadway productions and a male-skewing version of Girls Next Door, now in its sixth and final season on E! -- and, of course, the historic magazine itself.

The magazine, whose editorial operations are in Chicago, remains in Hefner's hands, though he now plays more of a supervisory role. "I'm still very active in certain aspects," he says. "I pick all the covers, pick all the Playmates, pick all the pictorials, edit the letters, party jokes, cartoons, approve all the layouts."

Ad pages declined to 357 in 2010 from 765 in 2000, according to the Publishers Information Bureau, but Playboy in the past year alone has added three international editions to its previous 28, with new magazines licensed to South Africa, Moldova and Mongolia. Flanders says the domestic version "loses a small amount," but that Playboy makes money from its international print operations.

Licensing -- not publishing -- is the company's future, he believes, and one he thinks will rescue an organization that lost $51.3 million in 2009, even if it entails plans to cut employees from 525 to 150 in 2012.

"[Licensing] is growing very rapidly and will approach nearly $50 million [in revenues] this year, compared to under $30 million when I arrived," Flanders says. "That business is enormously profitable."

Playboy's ability to change was made possible by Hefner's decision to take PEI private in March, buying it for $207 million in association with Rizvi Traverse Management -- a surprise, given the public perception that PEI was an out-of-control skier on a black-diamond slope. That impression was countered when Penthouse owner FriendFinder Networks Inc. tried to outbid Hefner and Rizvi Traverse, indicating the brand still carries considerable appeal.

"It's unfortunate that the company ever went public," Hefner says. "My motivation for doing that in the early '70s was to be a nice guy for my executives."

Now he owns almost 37 percent of PEI -- though he says that's only part of his total wealth, which he estimates at more than $100 million, more than twice the $43 million stated in his 2009 divorce papers.

Going private leaves Hefner in control of his two abiding passions: the magazine and the fabled mansion, appraised at up to $100 million, where Hefner lives rent-free. (He paid PEI, its owner, $53,593 per month when the company was public.)

Divorced since 2010 and securely in charge of both his magazine and home, Hefner feels more vital than in years, he says.

"Could I be in a better place and happier than I am today? I don't think so. In my wildest dreams, I could not have imagined a sweeter life."


Yet there's a vulnerability that makes one wonder if all is as idyllic as he makes it sound. And that feeling only increases a week later, on Aug. 30, when I'm invited back to see his 2,485-volume scrapbook collection.

It's a stunning archive detailing almost every aspect of his life, done with a deliberateness that indicates Hefner knew early on he wanted a legacy. It contains the good, the bad and the ugly: photos of Hefner at the beginning of Playboy, which he started in Chicago in 1953 after scraping together a few thousand dollars for a magazine that would have been called Stag Party if the title hadn't been taken; a copy of the famous nude Marilyn Monroe photo that graced the first issue, which sold 54,000 copies; critical articles about the death of Dorothy Stratten, a Playmate of the Year who was shot to death in August 1980 by her estranged husband, Paul Snider; and, somewhat weirdly, a psychologist's assessment of her lover, director Peter Bogdanovich -- a scathing Hefner critic -- whose origins not even the archivist can explain.

But the scrapbooks are nowhere near as interesting as Hefner's bedroom, just a few doors down on the same top-level floor.

It's 1:30 p.m. when I'm told the room has been tidied up and Hef is ready to let me in. And what I see makes me reel back in shock.

The place is a mess. Old magazines and papers litter the floor all around his giant, king-size bed, with its kilim-style comforter. There are notes on an upcoming movie he will screen at one of his famed movie nights; pages from his magazine; a New York Times book review and wads of documents only Hefner could possibly identify.

If the 21,000-square-foot mansion itself is immaculate, with its manicured lawns and almost total absence of anything salacious -- the home of an English country gentleman, one might suspect -- this huge, wood-lined room, with a spiral staircase leading to a private office equally unkempt, couldn't be more different. It's an intimate window into one man's unvarnished id, and at odds with his empire's sexual theme: Two couches are covered with hundreds of stuffed toys; there's a mantelpiece highlighting Frankenstein heads and a framed replica of a toy gun he had as a child; the whole place is crammed with relics from his past.

"It's controlled chaos," one of his colleagues laughs.

But it's the chaos, not the control, which is intriguing.

"I can be at my most creative like this," Hefner explains, as he wades through the clutter to show me a panel that governs everything in the room, from the curtains kept permanently drawn to the huge TV screen facing the bed.

He seems tired today, wrapping his black pajamas tightly as if to protect himself, walking somewhat gingerly around the room, appearing older and at the same time more gentle than when we met just the week before.

Maybe he's right; maybe the chaos is creative. But perhaps it also reflects an inner turmoil he refuses to acknowledge in a life that's been full of it.

Born in Chicago in 1926, Hefner grew up as the older of two siblings, with an accountant father who worked for the Advanced Aluminum Co. and a stay-at-home mother. An imaginative child, he funneled his energies into cartoons and editing his high school newspaper before majoring in psychology at the University of Illinois.

He attributes his rebellion to his parents' emotional restraint. "My folks were raised pure prohibitionist," he says. "They were very good people, with high moral standards -- but very repressed. There was no hugging and kissing in my home."

Hefner slowly turned against this upbringing. He graduated from college in 1949, married young and had two children, working as a copywriter for Esquire in Chicago before launching his magazine. He remained with his wife Millie until 1959, then moved into his first mansion in Chicago and embarked on the unfettered lifestyle that continued as he started to commute regularly to Los Angeles in 1971.

Those were heady days, but they changed with the 1975 suicide of his former secretary, Bobbie Arnstein, under pressure from the FBI to finger Hefner for drugs. The agency, on his trail since 1972, suspected him of covering up the use of illegal narcotics, though it never found proof.

Stratten's murder marked an even lower ebb, followed by the 1984 publication of Bogdanovich's The Killing of the Unicorn, which lambasted Hefner for creating an anything-goes environment that fueled Stratten's husband in his rage and in turn led to her death. The attack on the Playboy founder and Hefner's subsequent attempts to refute the book may have contributed to a minor stroke he had in 1985.

After that, he modified his diet, began to exercise and gradually withdrew from his hedonistic lifestyle, the wild parties, the endless orgies -- all of which seem like ancient history as one moves through the silent and almost empty mansion today.

This is, after all, the same locale where Warren Beatty, Jack Nicholson and James Caan were regular visitors; where group sex was as regular as breakfast; where Hefner himself indulged in an array of women -- sometimes singly, sometimes together, always without guilt.

His tastes then and now veer toward women who remind him of the movie stars he loved growing up, such as Alice Faye, though he currently favors blondes. "Picasso had his pink period and his blue period; I'm in my blonde period," he quips, though the woman who got closest to him, Barbi Benton, was a brunette.

None of them was his intellectual match. "I'm not looking for a competitor," he says. "I'm looking for a partner -- a romantic partner."

Like Crystal Harris?

He expresses no bitterness toward the former Playmate, despite that tell-all tale. "I was very surprised," he admits. "She was talking about a third person I didn't recognize. She felt very badly about it afterwards. She came over and wept. You know, she's the one that wanted to get married, not me. But I think that Crystal is more than one person; she's kind of lost at the center and was overwhelmed by the relationship, and got caught up in an affair while we were going together that I knew nothing about." 

As to the way they parted: "There was no disappointment in terms of not getting married -- it's the disappointment of the relationship going south," he says. "It wasn't that I wanted to be married; what I wanted was continuity. But I misread the signs."

He still receives several letters each week from women around the world who want to become his girlfriend. Does he not think these women may partly be lured by his money and power? "Of course," he says. "But what is anybody really attracted to?"

With the girls who apply, he checks out their pictures and invites some to visit. Those he likes remain. "I'm obviously a visual person, and looks and appearance are important, but it's pretty obvious also that I have a particular type," he acknowledges.

His second wife, Kimberly Conrad, a Playmate of the Year, fit the mold -- one reason he married her in 1989. He also was recuperating from illness: "I got married around 62 and I had just come out of a bad relationship with [Playmate] Carrie Leigh; I'd had the stroke; the times were very anti-Playboy and I was seeking a safe harbor. And, you know, I felt my years. I felt older than I did coming out of my marriage 10, 12 years later. We were not well suited. I just don't think we had that much in common."

Hefner says he remained faithful throughout the marriage; afterward, she moved into a house next door to the mansion before leaving Los Angeles for Reno, Nev. (She has since returned to the city.)

Her presence is long gone now, like so many of the mansion regulars --the late Robert Culp and Don Adams, to name just two -- men with Hefner for decades, whose ghosts float through his life in striking contrast to the dizzy young women who surround him in public.

"I lost some very dear friends," he reflects. "If I could have figured a magic way to save their lives…" his voice trails off.

The impact is so deep, he avoids the subject. He hardly ever talks about death, a close colleague tells me: "Even when [a longtime assistant] died, after the memorial, he never mentioned her again."

Is he afraid of the prospect? "No," insists Hefner, an agnostic who professes no faith in any afterlife. "My mother lived to 101."

"Look," the colleague presses on, "there's two ways to think about his hedonism: One is that Buddhist thing of living in the moment, and the other is a terrible fear of death."

Astonishingly, nobody in the company has addressed what will happen when Hefner himself dies. I ask Flanders about the succession and there's an agonizing pause. Finally he says: "That's hard to imagine. There's no succession plan."

Hefner's own hopes that one of his two younger sons -- Marston, 21, and Cooper, 20 (with Conrad; he has an older son as well as Christie, 58, with his first wife) -- might take over seem unfounded.

"At one point, I expected it to be a family thing," he admits, "but that's been squandered." He rephrases the wording. "I don't think that's in the cards anymore." Both boys are still in college and neither has yet had Christie's experience of joining PEI as a junior executive before climbing to the top.

Hefner has had other issues to deal with -- like the declining circulation of Playboy magazine from 7 million at its peak to 1.5 million today, and Christie's exit as CEO of PEI in January 2009, 27 years after she was named president, especially difficult for a man of Hefner's unwavering loyalty.

While Christie says she wanted to leave -- "It was something I knew that I was going to do for a number of years" -- Hefner takes responsibility for the timing. "The decision was mine," he says. "I mean, the time had come and I really felt I needed to refocus the company back to the original inspiration." It also occurred after PEI's stock had dropped from $11 a share to $2 within a year.

In May, Christie was named executive chairman of lifestyle and wellness company Canyon Ranch Enterprises; she is on the board of the Center for American Progress, consults for the Columbia Journalism Review and remains "very close" to her father, she says.

Hefner also has had to face ongoing criticism from feminists such as Gloria Steinem, whose adversarial relationship with him -- she calls the NBC series a "net minus" -- has an odd twist.

"Gloria and I go back a long ways," he notes wryly of the woman who went undercover as a bunny then wrote about her experience, "but it's more personal than you probably know. She worked as girl Friday for Harvey Kurtzman, who created Mad magazine, and he said, 'You gotta meet this girl, she's just like you: She can make a guy jump through hoops.' We actually exchanged phone calls and came very close to dating."

Criticism like hers -- certainly, slingshots from others on the left -- may sting more than he lets on. "Being attacked by right-wing Christians did not bother me," he says. "Being attacked by liberal feminists did."

Hefner has long been associated with First Amendment and other liberal causes. He created waves when African-Americans mingled equally with white performers on his early television shows and has given money to the Democratic Party, though he professes disappointment in President Obama.

That's just part of the perplexing tapestry of this man who also has granted prominent space in his publication to such major names as Arthur C. Clarke and Vladimir Nabokov, as well as interviews with the likes of Martin Luther King Jr. and Jimmy Carter (who famously admitted in his interview that he had "committed adultery in my heart many times").

Allying himself with intellectuals -- along with exceptional musicians and comedians -- was a brilliant strategy to make Playboy palatable, but one that Hefner maintains simply reflected "my own personal tastes" rather than any deliberate agenda.

Those tastes continue to define the magazine, despite others' attempts to change it -- including former Maxim editor James Kaminsky, who was hired briefly and left unceremoniously after struggling to compete with the "lad" publications.

Hefner resists reinventing the magazine, which retains its defining monthly interview and airbrushed pictorials, and is personally horrified by more hardcore pornography. "I find much of it tasteless," he says, while rejecting any notion he may have paved the way for the Internet's porn pandemic.

All of this belongs to a world decades removed from the one that launched Hefner on his journey. And it's hard to reconcile the tender, slightly fragile figure who stands before me today with the polarizing character he once was.

As we leave the bedroom, suddenly he bends to move the papers and clear a path for me -- and the sight of this man who's built an empire, who's changed the world, hunched over and struggling for balance, is ineffably touching.


Friday, Sept. 2, at 6 p.m., and it's movie night at the mansion.

Like most days, Hefner has followed his set schedule, rarely leaving the house. "I get up about 10, have breakfast in bed -- orange juice, sometimes bacon and eggs and half a grapefruit. Then I go down to the office, talk to my editors, go through the layouts and spend the afternoon doing whatever," he says. That "whatever" includes researching the films he screens, just like the one we're about to see tonight.

Some 15 friends and staff have gathered around two dinner tables, and there's a genuine sense of family. Hefner's younger brother, Keith, 82, who has worked as an executive for Playboy, is here; so is Hef's secretary of 42 years, Mary O'Connor, a woman whose old-school graciousness has nothing to do with the adult Disneyland the mansion is reputed to be. Among other guests are a Playmate-turned-assistant, but nobody famous. Even the parties that draw them tend to be more about fund-raising than hell-raising, such as a recent event for autism, which caused ripples when several guests fell ill.

Tonight, there's a printed menu, and a choice of fish or chicken -- organized with the perfect consideration for his guests that's Hefner's hallmark -- and behind us, the grounds stretch out, with their azure pool leading to the celebrated grotto that hasn't been used once in my three visits here.

Indeed, there's a stillness to the place, a silence that's quite different from the fantasy world of so many males' imagination.

After dinner, Hefner gently ushers us into the large living room where Peter Sellers' 1964 comedy A Shot in the Dark will play. Two nights a week are reserved for classic movies, and a third for more modern films like Crazy, Stupid, Love and Rise of the Planet of the Apes, both of which Hefner says he liked. (He also enjoys Dexter and Boardwalk Empire, but isn't a huge fan of TV.)

A handful of young women float in and out, barely noticed. There's almost nothing sexual about the ambience.

Hefner's two new girlfriends, Anna Sophia Berglund and Shera Bechard, are ensconced at his side in the front row -- both blonde, both a quarter his age, both more thoughtful than the gaggle of Girls Next Door. Even so, Hefner's friends have few illusions about their longevity. "You see the same drill," one shrugs. "First they start leaving the movie early, then they get bored with the backgammon games, then they're gone."

Hefner may be surrounded by friends; he may be bathed in his loyalists' love; he may have all the material things a man could desire, but something is wanting.

"I never found the ultimate soul mate," he confesses. And yet he continues to hope. "My love map is very much designed and written by Hollywood. But the truth of the matter is, I should be single. I'm better served that way. Maybe I don't pick the right women. Or maybe I'm just too complicated."

HEFNER THEN AND NOW: The mogul who built his fortune on sex also became an (unconventional) family man

The Playboy Club: Unlike NBC's The Playboy Club, Hefner says its real-life Chicago precursor never had anyone die there, though a mafioso did confront him once. "I said, 'You have your enemies and we have ours, and I think it would be a mistake to mix them.' And he accepted that and we never had any problems afterward."

His Youngest Sons: "I'm very close to both boys," Hefner says of his younger sons, Marston and Cooper. "Cooper is more like me, very creative. Marston is more serious. But they didn't fall very far from the tree and look remarkably like me."

His Daughter: Christie Hefner, 58, was brought up largely by her mother, Millie Hefner. She was named president of Playboy Enterprises at age 29 and remained at its helm until 2009, when she left after PEI stock had plunged. She says she is close to her father and recently spent two days with him at the mansion.

When Hef Met Hollywood: In 1975, Hefner moved permanently to his L.A. mansion, which became a gathering spot for Hollywood. And the town remains fascinated by him. Just recently, after canceling a two-hour special when Hefner's marriage to Harris was nixed, Lifetime rebranded the show Hef's Runaway Bride. He says Discovery has approached him for a new series, but he regrets that no feature film has been made about his life after multiple screenplays were developed with Imagine Entertainment. "The first writer came to the conclusion that the only way to really capture my romantic nature was through song," he laughs. Hefner loves Hollywood back and cites Casablanca as his favorite film.