From regimented routines to facing depression, ex-bunny Holly Madison on life in the Playboy Mansion

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Stylist’s Anna Hart talks exclusively to Holly Madison, the world’s most controversial ex-Playboy bunny about what life was like inside the Playboy Mansion

What’s the first question you would ask a Playboy bunny? A woman who chose to live at the Playboy Mansion for seven years as one of Hugh Hefner’s infamous stable of seven companions, rising through the ranks to secure the dubious title of ‘girlfriend number one’? Well, in a twist I never expected, I was given that chance when I met Holly Madison, author of new book, Down The Rabbit Hole: Curious Adventures And Cautionary Tales Of A Former Playboy Bunny. And my first question? Quite simply: why?

“I felt that if I could say I was a Playboy playmate, to make me stand out a bit, people would think I was something special,” she tells me. “Not just another girl, auditioning for acting roles in LA.” She has also remarked, “I thought I was an adult and I thought I was making my free choice. And I was. But I wasn’t sophisticated or really prepared. And I kind of got in over my head… I could understand how people thought it was strange. But I guess I wasn’t comfortable enough to explain why I thought it would be fun or why I thought it would be a good idea.”

Not many of us would choose to put our independence and self-respect on ice and supply sex-on-tap and ego-massages to a septuagenarian (he is now 89) who runs his house like a harem. Hefner himself is a 20th-century icon, his 29-room mansion is synonymous with sex, fame and general debauchery (the house itself is thought to be worth up to $54million, while Playboy Enterprises, his selfmade empire, was valued at $207million in 2011). He has surrounded himself with the adoration of respectable celebrities, from Lewis Hamilton to Leonardo DiCaprio. And then there’s his women, often the epitome of subservient sexuality, with silicon-enhanced figures, platinum tresses and fixed smiles. I’ve always been fascinated by what goes on behind the walls of the mansion, but, as a feminist, I’m more curious about what goes on behind the smile of a bunny girl.

Now, the world has a woman who is willing to spill on both counts. The name Holly Madison is instantly recognisable to reality TV fans who were glued to several seasons of the E! series Girls Of The Playboy Mansion (2007- 2010). If you’re more of a The Killing box-set woman, here’s a potted bio: in 2001 at the age of 21, stuck with college debts, new to LA from small-town Oregon, and working as a waitress in Hooters while trying to make it as an actress, Madison attended one of the infamous Playboy Sunday pool parties, having been offered an invitation by Hef’s doctor who spotted her modelling at a Hawaiian Tropic promotional event. She spent a year going to these Sunday parties, before asking, after a particularly debauched night of clubbing, if she could move into the Playboy Mansion. Hef looked her up and down, and said, “You can stay for a while and we’ll see how it works out.”

Thus began Madison’s seven years as one of Hefner’s rotating troupe of girlfriends, until their acrimonious split seven years ago. (He says they parted ways because he didn’t want marriage and children, she says it was because he was emotionally manipulative and she wanted her freedom.) Interestingly, since Madison’s book was published, Hefner has claimed she has chosen to “rewrite history” to “stay in the spotlight”. She has responded by saying everything in the book is “100% true. I just think it’s not the version of the story he would like to tell.”

Today, Madison is 35, married, mother to a two-year-old daughter, and after years remaining tight-lipped, she’s decided now’s the time for the memoir. “For years I thought it would be classy to not kiss and tell, but after a while you just get sick of having other people trying to tell your story for you,” she explains with her slight Oregonian twang. She’s sick of being judged as a “gold-digger or a prostitute”. She also notes that the version that prevails “is generally the one most flattering to Hef”.

Hefner has of course successfully cultivated a reputation as a loveable rogue, a sailor-hatwearing caricature whose womanising antics people seemed ready to forgive, because his world doesn’t seem real. Having worked as a cash-strapped writer for Esquire in the Fifties, he scraped enough money together to launch Playboy magazine in 1953, with nude pictures of Marilyn Monroe as the centrefold. It sold 50,000 copies and an empire was born. Playboy has since – somewhat surprisingly – become a brand that people still have a real affection for. Whether that’s because successful, beautiful women see it as a badge of honour to become a Playboy centrefold (Kate Moss, 2014), or that celebrities like Rihanna attend the parties, or that with his paisley smoking jacket, Hefner comes across as an avuncular figure in a Benny Hill parody, it’s adult entertainment that’s somehow permissible. Even the bunny costume is cheeky and coquettish.

In Madison’s efforts to set the record straight, she pulls no punches, albeit in her book. When I ask her questions about the seediest episodes in the mansion, she quotes from the pages as if there’s a script she won’t – or legally can’t – divert from. We learn that Hef offered her Quaaludes (Mandrax in the UK, a sedative) the first night she joined him at a nightclub, with the charming line, “in the Seventies they used to call these pills ‘thigh openers.’”

Madison declined (she doesn’t do drugs) but got roaring drunk, and later that night, she joined Hef’s girlfriends in his master bedroom to spend a few grim minutes under the world’s most famous ladies’ man. “By the time I was able to wrap my head around what was happening, Hef had moved on to a few of his girlfriends, before finishing off by himself, as he always did,” she writes. “There was zero intimacy involved. No kissing, nothing. It was so brief that I can’t even recall what it felt like, beyond having a heavy body on top of mine.” If this sounds horrific to you, it sounds horrific to Madison, too. “Today I want to hit ‘pause’, grab that young girl in the club and run.”

But she didn’t run. It was the next morning, hungover, ashamed but grittily determined to get something out of the experience, when she asked Hef if she could move in. “I knew that if I couldn’t find a silver lining, I couldn’t forgive myself for the night before,” she justifies to me.

Number One

After she moved into the house near Beverly Hills in LA, Madison and Hef swiftly bonded over a love of old movies, and her squeakyclean demeanour (as well as the no drugs rule, she didn’t date a ‘side boyfriend’ like others) soon saw her promoted to the coveted role of ‘girlfriend number one’, the chief courtesan in Hefner’s 21st-century harem. Hefner liked all the girls’ rooms to have pink walls and white carpets, and he paid for the girls to have plastic surgery (usually as a birthday present) and cars, but the favourite gift was a white gold diamond bunny pendant with a sapphire eye that each girl received when she became an official girlfriend. Madison, as girlfriend number one, was given a coveted yellow gold version. She also moved into Hefner’s master suite which takes up several rooms on the mansion’s second and third floors. “I don’t take relationships lightly, so I had to focus on Hef’s good qualities.”

“Um, his good qualities?” I ask. “They don’t exactly come through in the book.” In writing, Hef comes across as a controlling, paranoid and occasionally cruel character. She sighs. “His gentlemanly persona, his generosity to his friends, his sense of humour – I’d remind myself of these, and make excuses for the bad.” She called him ‘Puffin’, and nursed dreams of marrying him and having his children.

“Yes, I loved him. I was young and blinded by his fame and accomplishments. I’d never had much luck in love, so I convinced myself that guys my own age weren’t for me, that I was always meant to find Hef. Just like that, I was in love.”

Life at the mansion was creepily regimented for a supposed den of licentiousness and free love. Monday night was ‘Manly Night’, when Hef would invite his male friends over for dinner and a movie. Tuesday was ‘Family Night’, when Hef would see his ex-wife and their two sons. Wednesday and Friday night were ‘Club Nights’, when Holly and the others were expected to be ready for 10pm, for a night of clubbing in LA. Girlfriends had Thursday nights free (like Mondays and Tuesdays), but there was a strict 9pm curfew. “Apparently we couldn’t get into too much mischief outside the walls before that hour,” Madison notes, wryly. Saturday was a buffet and movie night with Hef, and Sundays were for the legendary ‘Fun in the Sun’ pool parties.

While the club nights were largely for show (“If there’s one thing Hef loves more than sex, it’s publicity” says Madison), the post-club orgy in his master bedroom was all too real. Her book is no tawdry tell-all, and she skims over the sexual nature of life in the mansion, so I have to ask: “Did you ever enjoy the sex?”

She pauses. “The sex was very routine, and something I don’t think any of the girls really enjoyed. We just wanted to get it over with. I just wasn’t into the group aspect. It was embarrassing, and it wasn’t something I would typically do in the bedroom.”

“Did Hef – this legendary ladies’ man – care about your sexual pleasure?” 

“No, I don’t think he cared if we enjoyed sex. But I don’t think he cared about my happiness at all,” she says, firmly. “He cared about his own happiness, nothing more. And he believed that all a pretty young girl could possibly want from life was a little bit of money and a little bit of fame.”

“Didn’t you find this unbearably insulting and patronising?”

“Yes, of course. He was so old-fashioned and stuck in his ways. I don’t think he ever considered a woman’s selfrespect, or need to be surrounded by people who care for her. He was always puzzled when a girl left.”

Former bunnies, however, haven’t been too kind about Madison’s admissions. Izabella St James, who also released a book in 2008 called Bunny Tales, has said that Madison’s account is a bitter reaction to Hef not marrying her while Kendra Wilkinson has called the revelations untrue and an exercise in revenge because she didn’t get her hands on Hef’s money.

But after a lifetime of being called a gold-digger, Madison is at pains to point out that money alone wouldn’t keep a girl in the mansion. Girlfriends were given a $1,000- a-week ‘clothing allowance’, which, as Madison points out, “roughly equates to a chorus girl salary at a low-paying show at Vegas.” The hope, for most girlfriends, was the chance to be a centrefold. This did bring in decent money, and was a significant boost to a wannabe model or actress’s career. “But by now Hef had realised that when he gave a girlfriend a centrefold, she’d never stick around for long,” she says. “So he developed a way to make the mansion situation still look enticing to young women, but without giving us the sort of independence for us to leave.”

Madison is evidently smart and self-aware; she was horrified to learn that people saw her and her co-stars in Girls Of The Playboy Mansion as role models. “I thought people were just laughing at us,” she says. “I thought of us as walking advertisements: ‘Don’t try this at home, kids’.” When you step over the threshold of the Playboy Mansion, you give your tacit consent to a lifetime of being judged. Just a few weeks ago a male radio host said to Holly, “Some people would call you the predator, taking advantage of an old, wealthy man.”

Her voice rises in anger as she relays her response: “Excuse me? I was in college, fresh off the bus from Oregon, and smart but totally naive. Hef was in his 70s, a business mogul, very used to getting what he wanted, and he had this entire system in place, which had been going on for years before he met me. I was just more meat for this factory.”

So why did it take her seven years to get out?

“People always ask me why I stayed so long,” she says with a sigh. “But that’s the million dollar question for every woman who has ever left a bad relationship. We all have that friend who sticks with a guy all her friends hate. In some ways my situation was unique, in other ways, it’s a very familiar relationship dynamic.”

I find myself nodding; she’s right, most of us may have once been, or known, that woman. And while Hefner was never physically abusive, he could be cruel and controlling. Madison recounts her bouts of depression, which got so severe she contemplated suicide.

“I asked Hef for help, and he told me I wasn’t allowed to see a psychiatrist. He knew they’d advise me to leave. It wasn’t about what was best for me. It was about him maintaining control.”

On another occasion, she received a “verbal smackdown” when she dared to wear red lipstick to a party. “Don’t ever wear red lipstick again,” he ordered her. “You look old, hard and cheap.”

I am outraged on her behalf. “Weren’t you tempted to shout ‘You’re a wrinkly old man, you don’t get to tell me I don’t look good’?”

“Oh, no,” she replies, sounding shocked. “I just wanted to be the best girlfriend he’d ever had.” Years of being treated as a trivial plaything by Hef, being judged by the outside world; I’m expecting Madison to have conflicted ideas about feminism. She doesn’t. “I definitely consider myself a feminist,” she says. “In fact, I call myself a born-again feminist.” Her invocation of the F-word has irked critics, who accuse her of hypocrisy, ignorance. “I just believe that we shouldn’t be branded for life by a decision we make aged 21,” she explains, hotly.

Feminism should have an opendoor policy. None of us are born a feminist, it’s a choice we make. And women like Madison who find feminism later in life, and who are prepared to talk about their mistakes and misogyny as well as their triumphs, help feminism reach other young women who still believe that sexual desirability is the pinnacle of achievement. She deserves to be heard. “For so many years I wanted to live this glamorous, adventurous life, so I’d brush aside any reservations about not being treated right,” she says. “But every woman, even if she doesn’t like the word, or has misconceptions about the word, comes to a point in her life where she’s a feminist.” Madison is living, breathing, walking proof that the fight for feminism is as relevant today as in 1971, when Hefner first bought that mansion.

Down The Rabbit Hole: Curious Adventures and Cautionary Tales Of A Former Playboy Bunny (Dey Street Books, £16.99) is out now

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