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Holly Madison reveals hell with Hugh Hefner in Playboy Mansion

FAKE sex parties, strict curfews and power games. Ex-Playmate Holly Madison has revealed the truth about the Playboy empire.

Playboy mansion hell ... Holly Madison has revealed what life was really like as Hugh Hefner’s girlfriend. Picture: Supplied
Playboy mansion hell ... Holly Madison has revealed what life was really like as Hugh Hefner’s girlfriend. Picture: Supplied

THIS, she thought, was clearly the way out.

She was Holly Sue Cullen back then, a girl from a small town in Alaska, and she’d come to Los Angeles to get famous. How, exactly, she didn’t know, but not long after arriving, she was spotted by a friend of Hugh Hefner’s and invited to a party at the Playboy Mansion.

She was 22-years-old, a uni dropout who’d picked up extra shifts at Hooters to make ends meet. Soon she’d become Holly Madison, one of the most ­famous Playmates ever.

“I felt like Playboy represented a key to the glamorous life — that it would be a stepping stone,” Madison told The New York Post. “Everyone just made the Playmates sound like a fun little sorority.”

In 2000, Hugh Hefner and the Playboy empire already seemed like a toothless relic. Yet as Madison writes in her new book, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, life behind the mansion walls was darker than she could have imagined.

“I had this image in my mind of being this liberated woman who was really adventurous,” Madison says. “I was not as sophisticated as I thought I was.”

Playmate ... Hugh Hefner and Holly Madison. Picture: Supplied
Playmate ... Hugh Hefner and Holly Madison. Picture: Supplied

Hef’s bedroom

After that first invite, Madison became a regular at the mansion, and when one of Hef’s seven girlfriends left, Madison saw her chance. She asked Hef if she could tag along the next time he took his Playmates clubbing in LA — something he did twice a week.

He was happy to oblige.

That first night was devastating. Madison was told by an ­alpha Playmate named Vicky to stick close to Hef. So, back in the VIP room, behind velvet ropes and security guards, this gaggle of 20-something girls drank and danced and fawned all over an old man who was hard of hearing and had no rhythm.

“‘Oh my God,’ I thought, genuinely mortified for him,” she writes. “Had no one told him how silly he looked? I felt a bit sorry for him dancing around like the punch line to a bad joke. Back then, he seemed like such a sweet man to me, and this felt unnecessarily cruel.”

Then Hef approached her, bent over and opening one hand to reveal a bunch of pills nestled in an old tissue.

“Would you like a Quaalude?” he asked.

Madison was mortified. “No thanks,” she said. “I don’t do drugs.”

“Okay, that’s good,” Hef said. “Usually I don’t approve of drugs, but you know, in the ’70s they used to call these pills ‘thigh openers.’ ”

Not so happy family ... Hugh Hefner with girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson in 2008. Picture: Supplied
Not so happy family ... Hugh Hefner with girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson in 2008. Picture: Supplied

Looking back, she writes, that was the moment she should have left, never to return: “It doesn’t get much creepier than that.”

But it does. Madison drank the night away, mixing vodka and champagne, in part because she knew what was coming: Even though the Playmates insisted that they didn’t actually have sex with Hef, she didn’t believe them.

“I knew when I accepted the invitation to go out with them that I was getting into something racy,” Madison says today. “Even though I knew these girls probably had sex with him, it seemed very humorous and light.”

In the limo, on the way home, one of the girls leaned over to Madison and told her that after a night spent clubbing, all of the girls were expected to party with Hef in his bedroom. Madison was broke and about to be evicted from her apartment, and she felt like she had no choice — being one of Hef’s girlfriends, having the chance to live with him at the mansion, all hinged on what she did next.

Star power... Melissa Taylor, television personality and model Holly Madison, Playboy founder Hugh Hefner, Crystal Harris and Anna Berglund in 2009. Picture: Ethan Miller/Getty
Star power... Melissa Taylor, television personality and model Holly Madison, Playboy founder Hugh Hefner, Crystal Harris and Anna Berglund in 2009. Picture: Ethan Miller/Getty

So she went with it, following the girls up the enormous staircase. First, they all washed their feet in the bathroom, and then changed, per Hefner’s puzzling preference, into matching flannel pink PJs. Madison was led into Hef’s bedroom, and here the illusion of glamour and decadence fell apart.

“As Tina led me into the bedroom, I stumbled over and weaved through massive piles of junk covering the floor,” she writes. “Ceiling-high piles of videotapes, stuffed animals, art and gifts littered the room. It was like an episode of Hoarders.”

The room was dark, illuminated only by the glow of porn playing on two huge TVs.

“The girlfriends, in various stages of undress, were sitting in a semicircle at the edge of the bed — some kneeling, some standing, some lying down,” she writes. “I sat myself on the edge of the bed — unsure of what to do next. I leaned into Vicky ... ‘Maybe if I hide behind her,’ I thought, ‘I’ll go unnoticed for the night.’ ”

Vicky wasn’t having it. “Fake the f**k!” she said.

Madison suddenly realised that all of the girls were simulating sex, pretending to hook up with each other while actually gossiping underneath the blare of porn and music. It was clear that all of them seemed to dread sex with Hef, and a new girl on the scene took the pressure off them. Vicky practically threw Madison under him.

That night, Madison was one of two fresh faces; the other was a girl named Candice, and they were the first ones to have sex with Hef that night while the others watched.

“Much to my surprise, my turn was over as quickly as it started,” Madison writes. “By the time I was able to wrap my head around what was happening, Hef had already moved on to Candice, then to a few of his actual girlfriends before finishing off by himself, as he always did. I have never had a more disconnected experience. 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.”

Regret ... Holly Madison said sex with Hugh Hefner lacked intimacy. Picture: Bryan Steffy/WireImage
Regret ... Holly Madison said sex with Hugh Hefner lacked intimacy. Picture: Bryan Steffy/WireImage

Even today, the shame and regret Madison felt about that night sticks with her.

“I remember feeling really s****y about it the next day,” she says.

Yet the next morning, she asked Hef if she could move into the mansion.

“That might seem counterintuitive — ‘I’m not into it, but I’ll come back for more’,” she says. “But I felt stuck in my life, trying to make ends meet. I lost the lease on my apartment. I felt like I’d already thrown myself to the wolves, so I might as well reap the rewards and not just be one more slut who walked through those doors.”

Facade with frills

Very quickly, Madison learned that everything about Hef’s life — and the lives of his girlfriends — was an illusion. The mansion itself was in grave disrepair, the carpeting stained with urine from his nine dogs. Most of the bedrooms had cheap, outdated and beat-up beds and dressers, and some of the girls taped over vents so they could smoke crystal meth without getting caught.

Every single bathroom, as well as the pool bar and tennis courts, was outfitted with a tray of vaseline, Johnson’s Baby Oil and Kleenex. Hef gave all of the girlfriends bunny necklaces, which Madison later learned were made not of diamonds but cubic zirconia.

There were a few areas in which he was generous, however, and they all went to appearances. Hef kept an open account at the José Eber Salon in Beverly Hills, best known for catering to Hollywood’s old guard, and the girls could avail themselves of any beauty treatment whenever they liked.

Hef also gave the girls a weekly clothing allowance of $US1000 ($1285) and would pay for any plastic surgery they wanted. In return, they were expected to follow his rules: Any night they weren’t out clubbing, they had a strict 9pm curfew. Wednesdays and Fridays were “club nights,” with sex always to follow. Like Joan Crawford and wire hangers, Hef had a rule about red lipstick — never to be worn, ever. There were to be no outside boyfriends and no talking to the male staff.

Sunday was movie night, and it was old-school and cheap.

“Armed guards would enter the mansion with giant film cans to screen the newest Hollywood blockbuster for us,” Madison writes. “Often times celebrities or other important Hollywood power players would join us and be relegated to spending roughly two hours squirming in uncomfortable folding metal chairs.”

The girls were not allowed to work, and Madison soon became bored and depressed. The Playmates were supposed to be icons of sexual freedom, yet here they were, locked up behind mansion walls like ’50s housewives. For lack of anything better to do, Madison decided to clear out Hef’s bedroom and organise his massive collection of scrapbooks and VHS tapes. Her worst discovery at the mansion, she says, was a tape labelled Girl and Dog.

“My stomach turned,” she says. “I was like, ‘What the hell is this?’ ”

Playboy publisher ... Hugh Hefner paid for his girlfriends’ plastic surgery. Picture: Charley Gallay/Getty Images for Playboy)
Playboy publisher ... Hugh Hefner paid for his girlfriends’ plastic surgery. Picture: Charley Gallay/Getty Images for Playboy)

‘Girls Next Door’

Over time, Madison became Hef’s main girlfriend, and she got in just under the wire: As more potential Playmates came around, Hef announced he was cutting back on expenses, and when a girlfriend named Tina stood up for a recruit — a girl named Whitney, who’d already joined the sex parties but wasn’t getting an ­allowance — Hef declined.

“Actually, Tina, I’m hoping with the next set of girls, expectations won’t be so high,” he told her. “Do you know I spent $US2 million just on girlfriends and trips in the past few years?”

“She’s putting in all this time,” Tina said, “and all she’s getting is a drink and a f**k!”

The table was shocked to silence, until Hefner replied solemnly: “I like to think of this as all of their dreams coming true.”

Cover girls ... Kendra Wilkinson, Holly Madison and Bridget Marquardt on the cover of Playboy Magazine. Picture: Supplied
Cover girls ... Kendra Wilkinson, Holly Madison and Bridget Marquardt on the cover of Playboy Magazine. Picture: Supplied

Madison’s depression, meanwhile, was intensifying. She was living as half of a bizarre old married couple. “The only difference,” she writes, “was one of us was actually old.”

The girls played power games with each other but ultimately were pawns in Hefner’s larger game: He thrived on keeping them all at war, because it ­allowed him ultimate control. Aside from one other Playmate, Madison felt completely alone. She was isolated from her family and friends, many of whom thought her life in the mansion was gross and a mistake.

“There were days I woke up,” she writes, “and just felt like falling to the floor because I felt so depressed.” She begged Hef to let her see a psychiatrist.

“He said, ‘No, I’m not going to let you see a psychiatrist, because they’re just going to tell you to leave — go talk to my secretary about it,’ ” Madison says. “So I just started planning how I was going to see someone on my own. He’s basically admitting that he knows the situation is messed up.”

Girlfriends ... Hugh Hefner with Holly Madison, Bridget Marquardt and Kendra Wilkinson on September 24, 2008. Picture: AP Photo/Matt Sayles
Girlfriends ... Hugh Hefner with Holly Madison, Bridget Marquardt and Kendra Wilkinson on September 24, 2008. Picture: AP Photo/Matt Sayles

The arrival of Kendra Wilkinson — then 19 to Hef’s 78 — jolted Madison out of her depression. Soon she’d be ageing out of the Playmate pool, and then what? By 2005, she’d begun to see a way out: The E! network had just begun filming a reality series with Hef and the Playmates, and The Girls Next Door became an instant hit.

Suddenly, she had an identity again, yet part of her still felt ruined from that very first night, damaged goods that no one else would want. She saw a shrink behind Hef’s back, and she came to realise that Hef picked women who were already vulnerable — herself included.

“We were all young,” Madison says. “He wasn’t interested in women over 28. None of us were from a big city or affluent backgrounds. None of us had ever seen the darker side of the entertainment industry.”

TV hit ... Hugh Hefner with girlfriends Holly Madison, Kendra Wilkinson and Bridget Marquardt in scene from TV program Girls of the Playboy Mansion. Picture: Channel 9
TV hit ... Hugh Hefner with girlfriends Holly Madison, Kendra Wilkinson and Bridget Marquardt in scene from TV program Girls of the Playboy Mansion. Picture: Channel 9

Madison took off for good in 2009 when she got an offer to compete on Dancing with the Stars. It was the first time she’d done something on her own in seven years, and she knew she could make it. Today, at 36, she’s married with a two-year-old daughter, Rainbow, and feels nothing but contempt for the man she once said she loved.

“The only thing he ever gave me is a little bit of fame,” Madison says. “Fame is not always worth it.”

Anyone experiencing depression or suicidal thoughts can get help from Lifeline (131 114 or lifeline.org.au) and Beyond Blue (1300 224 636 or beyondblue.org.au).

This story originally appeared in The New York Post.

Originally published as Holly Madison reveals hell with Hugh Hefner in Playboy Mansion

Original URL: https://www.themercury.com.au/entertainment/books/holly-madison-reveals-hell-with-hugh-hefner-in-playboy-mansion/news-story/9497caeaf744d3d3990d380c93e08126