By CHARLES McGRATH Published: February 3, 2011Hugh Hefner already has his final resting place picked out and paid for: a crypt next to Marilyn Monroe’s in the Westwood neighborhood of Los Angeles. Not that he has plans to use it anytime soon. Hefner, who will turn 85 in April, lives these days what appears to be the life of an invalid, or even of a cosseted mental patient: wearing pajamas all day; rarely venturing out of the house; taking most of his meals in his bedroom — the menu seldom varying, the crackers and potato chips carefully prescreened to remove any broken ones. He is hard of hearing in his right ear and has an arthritic back that causes him to lumber a little when he walks. But he is in otherwise enviable shape for an octogenarian.
Catherine Opie for The New York Times
Questions for Hugh Hefner: Sex and the Single Man (July 11, 2010)
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Catherine Opie for The New York Times
Fully recovered from a 1985 stroke, he appears to have all his marbles and an undiminished energy level. He still manages to have sex, popping Viagra as the occasion warrants. And thanks to the surprisingly successful reality show “The Girls Next Door,” he has a brand-new fan cohort: women, even many middle-aged ones, who no longer regard him as a degrading smut peddler — the publisher of a magazine that Gloria Steinem once said made a female reader feel like a Jew studying a Nazi manual — but as a benign and indulgent paterfamilias, a kind of fairy godfather turning worthy, wholesome-looking young women into platinum-haired, big-bosomed princesses whose every need is provided for.
Hefner — or Hef, as he is known to just about everyone — is famous for bestowing presents of plastic surgery on his many girlfriends and may well have gifted himself. His neck is taut and wattle-free. His skin, owing to infrequent sun exposure and generous bastings with baby oil, has a Madame Tussaud-like smoothness and suppleness. One former girlfriend has said that in the bedroom, with his clothes off, he practically glows in the dark.
Over Christmas, Hefner surprised celebrity watchers by posting on Twitter that he had become engaged to 24-year-old Crystal Harris, the latest and, if he is to be believed, the last in the endless string of young women who have paraded through his bedchamber: most of them blond, many with names ending in a vowel and all of them with mammary tissue that appears to have been injected with helium. Hefner has been married twice before, so the notion of his settling down again may represent the triumph of hope over experience. But a few days before Christmas, he told me: “This is it. This is a very, very special one. I expect to spend the rest of my life with her.”
A couple of weeks later, Hefner was on the business pages, trying to buy back his own company. That he is still around, still making news, is, depending on your point of view, either remarkable or a little embarrassing. He is, on the one hand, a great success story — a man who turned his sexual daydreams into a fortune — and, on the other, a fossil who doesn’t understand that the sexual revolution ended decades ago and that, in any event, it wasn’t for geezers. Some observers on Wall Street used to think that the best thing that could happen to Playboy would be for Hefner to act his age and honorably take up his slot next to Monroe. David Miller, an analyst at the investment firm Caris & Company, once said, “We believe that Mr. Hefner’s death could result in a material stock-price uptick.”
Last summer, however, Hefner startled even his own board by announcing that he wanted to make Playboy Enterprises, which he took public in 1971, private again. He offered the stockholders $5.50 a share, or more than 30 percent beyond what the stock was trading for. But this was slim consolation to investors who had been unhappily watching Hefner live like a sultan at their expense while the value of their shares declined to single digits from a high of $32.19. Strictly speaking, Playboy Enterprises, and not Hefner, owns the Playboy Mansion, a 1920s Gothic-style spread southwest of Hollywood. Hefner pays rent and covers non-business-related expenses. The company pays for the upkeep of the house and grounds, and the salaries of the 80-employee staff, which includes a round-the-clock kitchen crew and a team of 13 who take care of Hef’s personal and business needs. Last year Hefner’s bill was $800,000, while the company kicked in $2.3 million.
Early in January, Hefner sweetened his offer to $6.15 a share, and the board recommended that the stockholders accept it. Miller suggested recently that Hefner, who once said that his life would be over if Playboy was sold, was trying to cling to the magazine, which sooner or later would have been farmed out to a licensee had the company stayed public. But all along, Hefner’s position has been that the stock is undervalued, and David Bank, a media analyst at RBC Capital Markets, tends to agree. “I think Hefner is incredibly shrewd,” he told me. “But when I take off my analyst’s hat and put on my psychologist’s hat, it’s something of an enigma to me. I don’t know that many 84-year-olds who are reducing their liquidity.”
Whoever owns it, the Playboy empire is unlikely ever to regain its former glory or influence. The original clubs and resorts were closed years ago. The circulation of Playboy magazine, the bedrock of the empire, has declined from a peak of 7 million in the ’70s to 1.5 million today. The ready availability of Internet pornography has not been good for business, and for a while Playboy appeared to have been crowded off the newsstands by the so-called lad magazines — Maxim, Stuff, FHM and the like — which depicted a culture that was less about “mixing up cocktails and an hors d’oeuvre or two, putting a little mood music on the phonograph and inviting in a female for a quiet discussion on Picasso, Nietzsche, jazz, sex,” as Hefner wrote in his first Playboy editorial, than about guys chugging beer, telling fart jokes and giving one another wedgies.
But like its founder, Playboy magazine has survived, if a little wizened, longer than its detractors imagined. Of the major lad mags, only Maxim still stands, and one of its former editors, 36-year-old Jimmy Jellinek, two years ago became editorial director of Playboy, second in command to Hef. “I aged out of the Maxim demographic,” he said recently. “The lad mags were predicated on instant gratification, on living the consequence-free life. It was the credit boom, and money was free. You could do whatever you wanted. The magazines were both a symptom of and a metaphor for everything that happened.”
In the realm of men’s magazines, Playboy, which Jellinek champions with the ardor and occasional near-breathlessness of a convert, now represents enduring, old-fashioned values. Jellinek compared it to a vinyl record in a world of MP3 files.
Hefner still supervises the layouts and chooses all the photographs, which by today’s standards are practically chaste-seeming. Airbrushed and lustrous, their pubic hair (if there is any) as carefully fluffed as their tresses, the Playboy nudes are suffused with an unearthly, almost Platonic radiance; and as the critic Joan Acocella once pointed out, those enormous breasts, miracles of buoyancy and cantilevering, make the women seem less sexy, oddly, than childish and innocent. They’re like little girls with balloons.
In some ways the magazine is little changed from the one so many of us read in our youth. The Playboy Advisor is still there, dispensing worldly advice; the not-very-funny party jokes are still on the back of the centerfold; Gahan Wilson is still drawing cartoons; readers are still writing in to dispute who killed J.F.K.; and there is Hef himself, with his arm around a couple of blondes. Playboy continues to publish some very good writing, as it has since the ’60s, yet it remains a fantasy magazine of sorts, and nearly 60 years on, with Hefner still presiding, the exact nature of that fantasy seems a little clearer. The Playboy dream was never — or never only — about limitless, guilt-free sex; it was about limitless, guilt-free sex as a manifestation of a theme even more far-fetched but nevertheless surprisingly durable in the American imagination: the possibility that you might never have to do anything as embarrassing as grow old.
Hefner is a little odd, certainly, but not a sleazebag. He has none of Bob Guccione’s oiliness, or Larry Flynt’s leering vulgarity. His manner is open and direct, and his language is as clean as a Midwestern Rotarian’s. By his own lights, having purged himself of the shame and hypocrisy that is part of most Americans’ sexual baggage, he leads a life that is exceptionally honest and moral. It’s also a life that is exceptionally well documented. He has been written about so often and for so long that in interviews now he tends to recycle himself, saying the same things over and over again, not in a bored, rote fashion but as if they had just occurred to him. He complains a lot about America’s puritanical, contradictory attitudes toward sex and likes to say that he is a “one-eyed man in a blind world.” He also thinks that most men would kill to be in his place.
No one is more fascinated by Hefner’s success and longevity than Hefner himself. He is a self-inventor, in the great American tradition of Jay Gatsby, William Randolph Hearst and Howard Hughes (before he became a recluse and started hoarding his urine), and he is also a great self-chronicler, a kind of hyper Pepys. In the attic of the mansion is an archive of continually updated scrapbooks now closing in on 2,400 volumes. The later ones tend to feature page after page of photographs devoted to mansion get-togethers and theme parties: Hefner, sometimes a little weary-looking, smiling his trademark wide-mouthed smile while his arms encircle a clutch of smiling young lovelies, bare-breasted or not, depending on the occasion, who after a while grow indistinguishable. Leafing through the albums, you get the feeling that these events, once famous and risqué, now take place simply so that they can be documented and generate more photographs.
Far more interesting are the earlier volumes, some of which are collections of stuff Hefner began keeping as a child. They include cartoons, a series of detective stories modeled on Conan Doyle and several issues of an illustrated horror magazine called Shudder. Hefner — a dreamy, solitary child, bright but socially immature — was already a publisher of sorts, churning out copy and writing editor’s notes to his readers. Most remarkable of all is a comic book, called “School Daze,” that Hefner, or an alter ego called Goo Heffer, worked on all through his years at Steinmetz High School in Chicago, depicting the larksome good times of an inseparable group of high-school pals.
Hefner really was the center of such a group. At the end of his sophomore year, in the first of many self-transformations, he made himself over, changing his hair style, buying a new wardrobe, learning to jitterbug and turning from Hugh — skinny, awkward and self-conscious, to judge from photographs then — into Hef, or Hep Hef, a jive cat. The metamorphosis apparently worked, bringing Hefner newfound popularity. Yet the comic strip, painstakingly drawn, beautifully inked, suggests that he was also spending long hours in an imaginary high school of his own invention.
Later strips deal with Hefner’s Army career (he enlisted right after high school but became a typist and never saw any action) and with the creation of Playboy in 1953, when Hefner was 27 and at a low point in his life. “When I was young I always thought, I’m going to do something very special, or else I’m going to be nobody,” he told me, and in the early ’50s failure looked more likely. He had a crummy job, had only just moved out of his parents’ house and was frustrated with his marriage to Mildred Williams, a high-school classmate.
A late bloomer sexually, Hefner didn’t masturbate until he was 18, and after years of foreplay, he finally managed to lose his virginity when he was 22, but he read Kinsey as if Kinsey were a prophet and became a student of marriage manuals and sex handbooks. Playboy was the sort of sophisticated, sexually adventurous publication he fantasized about. He scrounged money, including $1,000 from his mother, and laid the first issue out on the kitchen table, writing much of the copy himself. His greatest piece of luck was his choice of the first centerfold: a nude calendar photo of Marilyn Monroe taken four years before. It remains by far the sexiest of all Hefner’s pinups. Where subsequent Playmates all have a health-club aura, as if they’ve lately come from the tanning bed or a Pilates session, Monroe, flushed and languorous, looked as if she just had an orgasm.
Playboy very quickly made Hefner a wealthy man, and by the end of the ’50s enabled the second great transformation of his life, when Hefner, now divorced, instead of just leaving little traces of himself in the magazine’s photo spreads — a necktie, a pipe, a cocktail glass — stepped forward and became Mr. Playboy, a debonair bedroom savant who actually lived the life his magazine dreamed about. From that point on it becomes increasingly difficult to discern where Playboy leaves off and Hefner begins.
You can see the transformed Hef most vividly in clips from “Playboy’s Penthouse,” a black-and-white TV show that ran for a couple of seasons in the late ’50s and early ’60s. There, greeting the viewer at the door to his top-floor pad, is tuxedo-clad, pipe-smoking Hef, looking a lot like Don Draper, giving a weekly house party for people like Tony Bennett, Count Basie, Buddy Rich and Sammy Davis Jr., who, at a time when white and African-American performers seldom appeared together, would drop by and entertain and sometimes (because real liquor was served and the show was shot out of sequence) start off tipsy and then sober up.
Mr. Playboy’s heyday was the ’70s, when, as the money poured in, Hefner took to wearing pajamas round the clock, working from his bedroom, where he also slept with pretty much whomever he chose, and jetting around in the Big Bunny, his customized DC-9. The ’80s, though, were his anni horribili. Overexpanded, the business went sour, Hefner clashed with the Reagan administration and the Moral Majority and in 1985 he suffered a stroke, in part brought on, he insisted, by the unfavorable publicity surrounding the 1980 murder of the Playmate Dorothy Stratten.
Hefner now says that his 1989 marriage to Kimberley Conrad, January Playmate of the Month the year before, was an attempt to seek refuge — a “safe harbor from the waves.” “I was not well, and I felt my years,” he told me. “I felt much older then than I do today.” He and Conrad broke up in 1998, though they did not divorce until 12 years later. “During the marriage I was faithful,” he said to me emphatically, “and she was not.” (Hefner, for all his advanced views, clings to the double standard and has never entirely got over his first wife’s admission that while they were engaged she had an affair with a high-school coach.) The aftermath, he now admits, was “overcompensation,” as he began dating posses of women, including one named Brandy and a pair of twins named Sandy and Mandy. “You can’t make this stuff up,” he said, laughing at himself. At one point, early in his ’80s, he was living with seven young women and trying vainly to enforce a 9 o’clock curfew to keep them from dating anyone else.
“You’d think that the well would run dry — the number of people willing to expose themselves by becoming Playmates,” Mary O’Connor, Hefner’s 82-year-old assistant, said to me. “But it doesn’t. It just keeps flowing.” O’Connor, who has worked for Hefner for four decades, is a tall, no-nonsense woman, a former car-racing promoter, who has seen just about everything. Back when Playboy was headquartered in Chicago, she ran the Playboy Mansion there when it was partly a dorm for the Bunnies who worked in Hefner’s club. Among her duties now, along with buying the fabric for Hefner’s custom-made PJ’s and making his health care appointments, is looking after the mansion’s guest list — the select few who, after giving their names to a speaker-equipped boulder by the main gate, are allowed to proceed up the driveway, past the “Playmates at Play” sign and perhaps a wandering peacock or two, and enter the fabled pleasure palace, scene of countless late-night, clothing-optional get-togethers — and inviting new female talent to Hefner’s parties and frequent movie nights. “I can’t tell you how many pictures we get from girls saying: ‘I love you, Hef. I want to be your girlfriend,’ ” O’Connor said, shaking her head. “Once we got an envelope from overseas, and there was no address except a drawing of a rabbit.”
The Sunday before Christmas, there were a number of potential Playmates on hand at the mansion, all in red dresses, many wearing Santa hats. They posed for pictures and stood around the baronial entrance hall, giving off an invisible force field intimidating to the shy middle-aged visitor. The first thing you notice about these women — or, to be honest, the second, but it seems impolite to linger on the first — is their skin: radiant, blemish-free, glowing with a dewiness that was presumably the epidermal standard in those ultraviolet-free days back in Eden. Had the weather been better (L.A. was in the midst of a nearly weeklong deluge), they might have visited the mansion’s zoo and aviary, bounced on the backyard trampoline, cavorted topless in the underwater grotto. Instead they played pinball in the game room, enjoyed cocktails and a buffet dinner and then assembled in the living room — some on the floor, some on Hef’s couch, their places as precisely allocated as the chairs at a levee of the Sun King — for a showing of that evening’s film.
Hefner loves movies, and screens at least three a week: a classic film on Friday and Saturday and a new release on Sunday. As many as 50 or 60 guests — old pals, hangers-on, assorted B-listers — will attend these screenings, which are part of a schedule as rigid and unvarying as that of a monarch. Monday night is Manly Night, when Hefner gets together with his cronies, many of whom have been showing up for years. Tuesday is Girls’ Night, when he plays games of Uno and dominoes with his retinue. Wednesday is reserved for cards (more ancient buddies), and Thursday is Family Night, for hanging out with Marston and Cooper, the sons from his marriage to Kimberley Conrad. There are also seasonal theme parties, like the ones for Easter, Halloween and Hefner’s birthday, and a naughty Midsummer Night’s Dream fete, held in August, not in midsummer, where the dress code specifies lingerie or sleepwear. These occasions figure in Hefner’s calendar the way Trooping the Colour and the annual visit to Balmoral figure in the queen’s — as rituals enshrined by custom — and they are, not coincidentally, a good place for a potential consort to be noticed. Hefner first glimpsed Kendra Wilkinson, a star of “The Girls Next Door,” who now has a reality show of her own, when she was passing out Jell-O shots while wearing nothing but some strategically placed body paint at his birthday party in 2004. He spotted Crystal Harris, dressed as a French maid, at his Halloween party in 2008.
What do the women see in him? A friend, a mentor and a meal ticket more than a sex symbol, most likely. Live-in status at the mansion brings with it — or used to bring, before Hefner pledged himself to Harris — a stipend of $1,000 a week, paid out in cash by Hefner every Friday, and there was also free hair care, a car allowance and additional sums available for breast and dental implants and for special-occasion clothing. Sex with Hefner was not a requirement, strictly speaking, though most of his girlfriends did sleep with him, it appears, either out of gratitude or because of pressure from the others.
When I asked Crystal Harris whether her relationship with Hefner was sexual, she looked at me for a moment. “I don’t know how to respond to that,” she said, and then added, after a pause: “You mean sexual relations? Sure.” But she went on: “Hef has hooked up with a lot of people, but that’s not what makes him happy these days. He’s much happier just cuddling and snuggling with the dog.” They watch a lot of old movies together, she said, and she also likes trying to break him out of his unbudging routine. Just recently she persuaded him to try sushi and shepherd’s pie.
“Well, I guess I know what I like,” Hefner said when I asked him if he didn’t think it odd that as he got older and older, his girlfriends remained the same age, all in their 20s and all conforming to an unoriginal model of perky blond buxomness. He was in his standard daywear — red silk smoking jacket and black silk pajamas — and sipping a Pepsi while sitting in the mansion’s largely bookless library underneath a huge breast-baring ceramic bust of Barbi Benton, one of the few brunettes ever to catch his eye. “You do give up something in the process,” Hefner went on, acknowledging that most of his girls have never listened to his kind of music — jazz and the big bands of the ’30s and ’40s — and have never heard of Betty Grable and Alice Faye (who probably imprinted that sexy blond template on him in the first place). “But you gain something, too. There is something wonderful in the student-teacher relationship — the rediscovery, the chance to have a relationship with a younger woman. It permits you to see the things you love with a fresh eye, makes them exciting again. And I don’t think there’s any question that surrounding yourself with youth keeps you younger.”
This avuncular, nurturing Hefner, and not the sleek, night-owl playboy of decades past, is the one who emerges on “The Girls Next Door,” and may account in part for the success of that show. “The Girls Next Door,” which the E! network began showing on Sunday evenings in 2005, surprised even people at E! by attracting a huge viewership primarily composed not, as you might imagine, of heavy-breathing teenage boys but of women in the very profitable 18-to-34 age group. Even Kevin Burns, a friend of Hefner’s who produced the show, has trouble explaining its appeal. One of his more recondite theories is that the three girls (besides Wilkinson, there were Holly Madison and Bridget Marquardt) happened to illustrate the Aristotelian triad of ethos, logos and pathos, or honesty, brains and emotion. Hef, on the other hand, as the critic Daphne Merkin has pointed out, seems less lascivious than distantly, absent-mindedly affectionate. He’s like the TV dad on “Father Knows Best” and other Stone Age programs.
People in the Playboy company talk a lot about the “brand,” a sort of emanation from the magazine that they believe has in some ways transcended Hef himself. Hefner’s daughter, Christie, who was chairwoman and C.E.O. of Playboy Enterprises from 1988 to 2009, told me that once when she was in China, where there are hundreds of stores selling Playboy merchandise but where the magazine itself cannot be published, someone asked when her father had joined the company. The brand is a label that can be attached to stuff — not just thongs and rabbit-head necklaces like the one Carrie Bradshaw wore for a while in “Sex and the City,” but bar glasses, pool cues, bath and shower products and tank tops for dogs — and there is a huge and growing market for this merchandise overseas, especially in Asia and Eastern Europe.
The brand, not the magazine, is the moneymaker these days. Playboy is getting back into the gambling business, licensing its brand to casinos in Macau and Las Vegas. The Playboy television channel, meanwhile, is trying to advance from raunchiness to coolness with its new Saturday-evening program, “Brooklyn Kinda Love,” in which Brooklynites all appear to be childless, pierced and tattooed. An elderly pipe-smoking gent in a bathrobe would be weirdly out of place here. Yet the Playboy brand still depends at some level on the imagery of the debonair smoothie who created the magazine, the kind of guy who knows his way around the bedroom but is also well informed about neckwear, stereos and shoe care and who gives big parties at his mansion.
Hefner is “iconic,” his friends and associates like to say, and lately there has been an effort to burnish and preserve the icon. In 2008 Steven Watts published “Mr. Playboy: Hugh Hefner and the American Dream,” an authorized biography that treated its subject with the care and depth usually reserved for statesmen and political figures. Last summer, Brigitte Berman came out with “Hugh Hefner: Playboy, Activist and Rebel,” an adulatory documentary film (made with Hefner’s cooperation) that emphasizes his many contributions to civil rights and freedom of speech. For years now the producer Brian Grazer and the director Brett Ratner have been talking about making a biopic, possibly starring Robert Downey Jr., and there have even been discussions about a possible Hefner musical.
What happens if, or when, the icon is no longer personally available is inevitably on the minds of many people associated with Playboy. Though he is not pushing a succession plan, Hefner is pleased that his sons — Marston, who is 20, and Cooper, who is 19 — have begun to take an interest in the magazine. He told me that Cooper, an avid cartoonist, reminds him a lot of himself at the same age. To judge from a couple of brief conversations, however, neither of the Hefner boys shares the braininess of their 58-year-old half-sister, Christie, a summa cum laude Brandeis graduate; nor, for that matter, do they display much of the self-inventiveness, born both of awkwardness and ambition, that characterized their father at the same stage in his life. They’re sweet and slightly spacey and seem a little young for their age — a result, probably, of growing up in a world that is a real-life version of what is for most adolescent boys only a guilty fantasy.
“I prefer to think of it as when he’s not active, not when he’s not around,” Christie Hefner said, talking about the future. She and Richard Rosenzweig, the executive vice president of Playboy Enterprises and a longtime friend of Hefner’s, like to imagine that he will become a beloved, eternally brandable figure like Walt Disney. “It will be easier to perpetuate my story when I’m not around,” Hefner told me. “Because then nobody will be pissed off that I’m still getting laid.” He also pointed out that his mother lived to be 101. Then he went back upstairs to his legendary bedroom, which these days is a bit of a mess: stacks of old movies on tape and DVD, knickknacks and tchotchkes everywhere, childhood photographs on the mantel, panties dangling from a chandelier and, nestled together on a sofa, a couple of hundred stuffed animals. It looks less like a love nest than the cave of a hoarder unable to let go.