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30 January 2024

The sexual revolution that failed

Crystal Hefner on life inside the Playboy mansion and surviving the “trauma” of her marriage to the notorious libertine.

By Pippa Bailey

Crystal Hefner’s favourite film is The Little Mermaid. When her late husband, Hugh Hefner, the Playboy tycoon and notorious libertine, proposed in 2010, he presented her with a music box. Inside was a miniature Ariel, who twirled to “Part of Your World”, and a ring. “I hope it fits,” was all Hefner said; he never asked her to marry him, and she never said yes. “It wasn’t a question. It wasn’t a choice,” Crystal writes in her new memoir, Only Say Good Things. “Like all things with Hef, it was a transaction.”

The parallels between the life of the Disney princess who trades her voice for love and the Playboy centrefold who lost her twenties to Hefner are clear. When Crystal first visited the faux-Tudor Playboy Mansion in Holmby Hills, Los Angeles, she found that “everything was so ornate and everything’s in excess. I thought, wow, I want to be part of this powerful, beautiful world… This finally could be a place where I feel like I belong.” Crystal only left the mansion when Hefner died, aged 91, in 2017.

Today, she divides her time between LA and Hawaii, where she owns a small farm. At the time of his death, Hefner no longer owned the mansion, but leased it from the billionaire he had sold it to, and their prenuptial agreement gave Crystal no claim to his fortune. Instead, she inherited a house nearby (she never moved in as the paparazzi had staked it out) and his retirement fund. She works in property, and sits on the board of the charitable Hugh M Hefner Foundation. The Playboy trademark bleached hair is gone, as are the breast implants. Looking back on photographs from her former life, she told me during a video call from LA, “I feel like I look like a sex doll from China… It was awful.”

Hefner’s rules were strict. “I had to be malleable. Compliant. I had to let people touch me, casually, like I was part of the mansion decor,” she writes in Only Say Good Things (the title is a promise Hefner asked her to make before he died). The ideal Hefner women were slim – Crystal had liposuction, and a nose job – and their hair white-blonde with no roots showing. Nail polish had to be light pink and translucent, and they could never wear dark lipstick; “Women who wear red lipstick look like harlots,” Hefner said. Also banned was birth control; if anyone caught an STI, Hefner had a private doctor on hand to treat them.

Time at the mansion was regimented: Tuesday was game night (dominoes and Uno); on Thursdays they went out. Fridays and Saturdays were movie nights, and Sundays the “false fun in the sun” parties. “It was miserable… like a cruise-ship itinerary,” Crystal said. Once a week the women had to ask Hefner for their allowance, $1,000 dollars in cash, which Crystal found humiliating. Most nights she had to be home by 6pm. “It was a curfew disguised as a schedule.”

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By the time Crystal left the mansion, she was so used to being home before dark that she realised she did not know how to turn on the headlights in her own car.

Of the thousands of women she met over the years, Crystal said, she made only three friends. “It was lonely being surrounded by so many people. It was all noise just swirling around you and you’re really alone. Most of the people there want to be a playmate or be close to Hef. The people who work for him just work for him, and it’s Hef everything, living to please Hef’s wants and desires.”

Crystal experienced panic attacks and paranoia. Hef had a key that could open any door in the mansion. She claims her husband took compromising photographs of the women in his entourage on nights out, and used hidden cameras in his bedroom to secretly film those he had sex with, until he was scared into destroying the recordings by the Pam and Tommy sex tape leak in the 1990s. A photographer “would follow us everywhere”. She recalls hearing the “snap-snap” of the lens and wondering: “Is she trying to… catch me in something? Or I’d be in the vanity having a private conversation [on the phone] with my mom and you’d see under the door someone walking by, the shadow. It all caves in on you.”

Hugh Hefner was born in 1926 in Chicago, the son of Glenn, an accountant, and Grace, a teacher. In 1953 he launched Playboy (working title: Stag Party) – a rebuke to a culture of American puritanism at a time when doctors still refused contraceptives to single women. Marilyn Monroe graced the first cover of Playboy magazine, but she did not consent to it, or receive a fee: Hefner bought the images from a calendar company. Playboy was, as the commentator William F Buckley Jr clinically put it in 1966, known for its “total exposure of the female form”. But it also published fiction by Vladimir Nabokov and Kurt Vonnegut, and interviews with Jimmy Carter and Jean-Paul Sartre. At its peak, its circulation was seven million. On the magazine’s success, Hefner built a global empire, including the members-only Playboy Clubs, at which the “Bunny” waitresses wore corsets, floppy ears and fluffy tails – all his design.

For Hefner, Playboy wasn’t just titillation: he aimed to create a new morality. The “Playboy philosophy”, which Hefner wrote in 25 instalments from 1962, was, he said, “an attempt to re-evaluate some of the social and sexual ills of our time”: purity, tyranny, absolutism. Many of his causes – legalising marijuana, abortion rights – prevail today. Some saw Hefner as liberating America from social and moral conservatism. To others, he was a misogynist who created another men-serving role for women to fulfil: if you didn’t want to be a housewife, you could be a sex object instead. Hefner’s revolution may have been abhorrent to conservative-evangelical America, but it was also curiously safe. For all he professed to loathe the concept of a “code” by which to live, his ideal of beauty and female sexuality was particular and closely controlled, crafted only to fulfil his fantasies – to the extent that the Harvard theologian Harvey Cox once called it “basically anti-sexual”. At the “Casablanca nights” that were a mainstay on the mansion schedule, Hefner aired old movies and gave speeches about their merits. “He was attracted to the damsel in distress: the women that would faint and be helpless or have big dresses and couldn’t really move around very well in them,” Crystal said, and I thought of the stories of former Bunnies: how their metal-stayed corsets were so tight they sometimes induced kidney infections.

Crystal Hefner was born 60 years after her husband, in Lake Havasu City, Arizona, in 1986. Her father, Ray Harris, was a singer; her mother, Lee, had two daughters from a previous marriage. The family moved between the US and Britain (at one point they ran a pub, Ye Olde Rose and Crown, in West Bromwich, near Birmingham), before settling in California. When Crystal was 12, Ray died from a brain tumour. The family moved in with Lee’s boyfriend who, in Cinderella fashion, adored his daughter but neglected Crystal. It was in his office, aged 14, that she first saw an issue of Playboy, and thought: “Wow, these women are beautiful and powerful. And they have the world at their feet.” 

Crystal was 21 and studying for a degree in psychology at San Diego State University when a friend encouraged her to attend a Halloween party at the Playboy Mansion. Out of the hundreds of girls dressed like French maids, it was Crystal at whom Hefner crooked his finger in a come-hither motion. That night, she slept with him for the first time, at the same time as several other women. The sheets were black silk, the lubricant baby oil. Four televisions in the low-lit bedroom were playing pornography, and Madonna’s “Dress You Up” was on the stereo. “Even that first night,” Crystal writes, “[the sex] felt odd and robotic – like Hef was just going through the motions of something that had once been fun and sexy.” It never improved. Hefner was, Crystal told me, “like a fumbling college student”: “He did not know how to please a woman at all. You think… he’s a sex god. But no, he wasn’t, he had no clue. I think he didn’t need to have any clue, people just did whatever he wanted.”

Yet the mansion felt “like a safe place, and Hef was very charming and magnetic. I did feel, OK, I will be… protected by this person.” When she was invited to move in as one of his girlfriends, she – perhaps naively – believed they would fall in love. But “he couldn’t truly connect because he was narcissistic. It was all about himself.” There was no place for romance or monogamy in this public harem.

When the couple married, on New Year’s Eve in 2012, Crystal was 26, Hefner 86.  “I would like to think that he grew up a little bit before he passed away,” she told me. Hefner credited Viagra with reviving his sex life and was dubbed the drug’s “patron saint”. (According to Crystal, he took so much it damaged his hearing.) But by 2014 the sex, which Crystal viewed as a job, stopped altogether, as did bringing new girls home.

Why did she stay for so long? “Because I really wanted to? Because of Stockholm syndrome? I’m not really sure… I didn’t know what boundaries were at that time. And it was pre-#MeToo…’” Hefner died just a month before the #MeToo movement began. Would he have survived the reckoning? “I don’t know,” she said. But the Playboy brand “is surviving in a different way now, so…” The sexual revolution Hefner helped engender has long been held up by progressives as a positive force, but today the backlash, which holds that the ensuing pornification of society harmed both men and women, is growing. When we spoke, Crystal traced a line from Playboy to more explicit magazines such as Hustler, to the proliferation of free internet porn. “So did he help society?” she asked. “Or did he hurt it?” It is hard to read Only Say Good Things as a case for the former.

In a porn-saturated online world, what survives of the Playboy brand is no longer shocking, perhaps even passé. Playboy magazine is now online-only, having ceased print publication in March 2020. For a subscription, you can access the magazine archive on its website, along with adult photographs and films. The last Playboy Club in the US closed in 1988 (an ill-judged attempt to open one in Manhattan in 2018 lasted just a year); today, it exists only as a “digital destination”.

In the wake of Hefner’s death, Sarah Kate Ellis, the president of the LGBT organisation GLAAD, wrote: “Hefner was not a visionary. He was a misogynist who built an empire on sexualising women and mainstreaming stereotypes that caused irreparable damage to women’s rights and our entire culture.”

“I definitely didn’t feel liberated,” Crystal said. “I think a lot of it was disguised as that. If anything I felt controlled and… completely trapped. That’s the opposite of sexual freedom and expression.”

And yet, Crystal Hefner does not consider herself a victim. “It was my choice. I was 21 [when she entered the mansion], which is young. But it was my choice. I don’t regret it. I think my story’s a good story. I think it was weird. It was traumatic. But everything happens for a reason.”

I wondered, if she could make the choice again, would she have gone to that first Playboy party? “I would probably have stayed at home and done something else.”

Is this the lesson of the sexual revolution: stay at home?

[See also: Are you ready for Elon Musk to read your mind?]

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This article appears in the 31 Jan 2024 issue of the New Statesman, The Rotten State