Holly Madison Compares the Playboy Mansion to a Cult and More Bombshell Claims About Her Time With Hugh Hefner

Credit: Mediapunch/Shutterstock

Holly Madison Compares the Playboy Mansion to a Cult and More Bombshell Claims About Her Time With Hugh Hefner

No matter how much time passes, Holly Madison’s bombshell claims about the Playboy Mansion never fail to ruffle some bunny feathers. Madison dated Hugh Hefner from 2001 to 2008, with E! cameras documenting three years of her romance with the Playboy founder on The Girls Next Door. While she was Hefner’s “main girlfriend” after his split from Tina Jordan, Madison became known as part of a trio alongside Bridget Marquardt and Kendra Wilkinson. The Holly’s World alum initially detailed her time in the mansion in her 2015 memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, alleging that Hefner offered the women drugs and detailing the bizarre rules and regulations amongst the women. “I thought I was an adult and thought I was making my free choice. And I was,” she wrote about her decision to move into the mansion. “But I wasn't sophisticated or really prepared. And 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.” More than five years after the memoir made headlines, Madison got candid about her relationship — and sex life — with Hefner during an appearance on the “Call Her Daddy” podcast. “I started to feel like I was in love with him,” Madison told host Alex Cooper. “Looking back at it, it was a very Stockholm syndrome kind of thing where I felt like I identified with him, he was complimenting me so much, I started, in my mind, started blaming all the other problems on the other women." [jwplayer JKukwYEW-l3ahXupL] Hefner and Madison split in 2008 after Marquardt and Wilkinson decided to move out too. “He started lashing out at me more for really stupid things and I just realized, like, I can’t be here, like, this guy is an a—hole. But even still, I felt guilty leaving,” she recalled to Cooper. “It took time, it took me being interested in another man before I finally was like, ‘I have to pull the plug because I’m not gonna cheat.’ It just goes along with all the love-bombing stuff and the ‘We’re gonna be together forever, and we’re gonna be together the rest of my life’ and blah, blah, blah. He would compare me to Belle in Beauty and Beast, like, I just came along to this castle.” Hefner, who went on to marry Crystal Hefner (née Harris) in 2012, died in 2017. After Madison’s book came out, he told Us Weekly in a statement: "Over the course of my life I've had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy, and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes, 'You can't win 'em all!'" Scroll through for the most telling quotes from Madison about her time in the mansion: [podcast_block]

Credit: Rich Fury/Invision/AP/Shutterstock

The First Date

During a December 2021 appearance on the "Power: Hugh Hefner" podcast, Madison detailed the first time she had a sexual encounter with Hef. "I thought it would be more of a first date, even though, obviously, it's not a very traditional first date," she recalled. "I wasn't necessarily expecting to have sex that night. I was not expecting to be the first one to go [with him] that night, but I was wasted. He was literally pushed on top of me. After it happened, I was just mortified and embarrassed and it had way more of an emotional impact on me than I thought it would."

Madison explained that she was upset by the fact that other people in the mansion knew what happened between her and Hefner. "It was more the group aspect that was really out of my comfort zone. That happened. Everybody knows it happened," she explained. "I hadn't heard a lot of talk about what went on upstairs. All of a sudden, it felt like everybody was going to know about me, and I was horrified by it."

Credit: Shutterstock

The Hair Cut

In a sneak peek for A&E’s Secrets of Playboy documentary event, Madison claimed that Hefner flipped out on her over a haircut.

"I got to a point, not too far into my time there — I think it was, like, six months in — where I kind of broke under that pressure being made to feel I had to look like everyone else. My hair was really long naturally, and I was just like, 'I'm gonna go chop my hair off so I can, at least, look a little different,'" she claimed. "I came back with short hair, and he flipped out on me. He was screaming at me and said it made me look old, hard and cheap."

Credit: Shutterstock

Scary

"I didn't realize that getting into the Playboy world was a dangerous choice," the model said in the promo for Secrets of Playboy released in August 2021.

Credit: Courtesy Holly Madison/TikTok

Struggling With Body Dysmorphia

Madison revealed she struggled with her body image issues during her time in the mansion via a July 2021 TikTok video.


“So for a recent post, I was looking for pictures of myself in a bunny costume and I came across one. It reminded me of a moment in my life where I was watching a playback of myself in a fashion show and I thought, ‘Oh, my God, I need to lose weight,'” the former reality star explained in the clip, alongside a photo of her from 2005. “[I] thought I had gained weight, and thought I hadn’t stuck to my diet, and I thought my thighs were huge and I thought, ‘I need to lose five pounds at least.’ And that’s ridiculous. I look like a stick.”

Credit: Jim Smeal/BEI/Shutterstock

You Have to Sleep With Hef Before You Move In

While Wilkinson previously claimed that she didn’t have sex with Hefner before she moved into the mansion, Madison alleged on “Call Her Daddy” that she was lying.

“I had to sleep with him first,” Madison told Cooper. ”I’m not trying to slut-shame anybody or anything, but nobody ever got asked to move in unless they had slept with him.”

Wilkinson, for her part, fired back via Instagram in April 2021, replying, “Dude… it’s 2021 😂. Times have changed. I forgive and have kids to love and focus on.”

Credit: Dave Allocca/Starpix/Shutterstock

‘Cutthroat’ Environment

Madison told Cooper that the women in the mansion would tell Hefner’s secretaries if they thought the other girlfriends were pocketing their weekly $1,000 “allowance” and not spending the money on their appearance.

“It was horrendous the first three or four years I lived there. Before it was just me, Bridget and Kendra, it was me and six other women and it would rotate every couple years,” she said. “It was really cutthroat, nobody got along, everybody tried to snitch on the other or tell Hef a lie about the other to get someone kicked out.”

Credit: Peter Brooker/Shutterstock

Holly Didn’t Have Sober Sex With Hef

“I don’t remember a time in that bedroom I wasn’t wasted,” Madison told Cooper, alleging that Hefner offered her Quaaludes or "thigh openers” before they had sex for the first time.

"Everybody would go upstairs and basically everybody would have sex and I didn't know what to expect," she recalled of her first time having sex with him. ”I think I had the feeling that, this is my first night out, maybe I won't be expected to do anything my first night. But then when I got up there, I was so wasted and thrown into it, that once it was done, there was something about the experience that made me feel very out of control."

Madison recalled the Quaaludes story in her book too. “’Usually I don't approve of drugs, but you know, in the '70s they used to call these pills thigh openers,’” she claimed he said to her at the time.

Credit: Shutterstock

Grateful She Didn't Get Pregnant

Madison has been open about the fact that she tried to have a child with Hefner during their relationship. She told Cooper how grateful she was that her attempts to conceive didn’t work out.

“I knew it was because of him. I was healthy. He was just too old,” she said. “When I had first gotten into that situation and something happened in my mind that first night I had sex, where I felt like, ‘Ok I did that. I like breached my own boundaries and I wasn’t comfortable with it. Now I have to make this situation into something.’ I almost locked myself into this box.”

Credit: Broadimage/Shutterstock

The Rules of the Mansion

Madison told Cooper that living in the mansion felt like a "life sentence" with “cultish” rules.

“It's a very cult-like atmosphere anyway and you're manipulated to feel that way, but on top of it, my own shame kept me there too. I just couldn't really imagine a life outside of there,” she said.

Madison also detailed the rules of the mansion, including a 9 p.m. curfew and having group sex with Hefner twice a week.

“Imagine having sex with somebody in a room full of women who all hate you and you know they're all talking s—t about you. Like, how horrible?” she told Cooper. “It was gross."

Madison shared more NSFW details, alleging that Hefner wouldn’t “pleasure” the women, explaining that if they had their underwear on in the bedroom it was a signal they were on their period or didn’t want to have sex and claiming that Hefner “would get mad if somebody wasn't shaved.”

Credit: Sipa/Shutterstock

Hef Started Drama Among the Women

Madison claimed in her book that Hefner created drama within the house over living arrangements and their appearances. She recalled one alleged incident when Hefner called her “old, hard and cheap” for wearing red lipstick before praising Wilkinson for the same look. When asked about her status with Wilkinson in April 2021, Madison simply said they weren’t in touch. She told Cooper that she and Marquardt, meanwhile, have “always been close."

Credit: Marion Curtis/Starpix/Shutterstock

‘Girls Next Door’ Claims

Madison alleged in her book that she, Wilkinson and Marquardt weren’t paid for season 1 of the E! series. During her candid chat with Cooper, she said the three girls were “under duress" when they signed the contracts.

“They just thought that because we lived there, they just owned us,” she claimed. “I didn’t want to sign it because I felt like it was creepy … It felt like it was a contract to be in a relationship. … [Hef said], ‘That’s sweet, but we need it today or E! isn’t going to order the show.’ And I don’t really believe a network would operate that way so I think they were lying, but it was a creepy.” 

Credit: Mediapunch/Shutterstock

Very ‘Cult-Like’

“The reason I think the mansion was very cult-like, looking back on it, is because we were all kind of gaslit and expected to think of Hef as, like, this really good guy,” the Holly’s World alum said in the Secrets of Playboy docuseries, which premiered in January 2022. “You started to feel like, ‘Oh, he’s not what they say in the media — he’s just a nice man.’ Another thing that reminds me of a cult is how it was so easy to get isolated from the outside world there. You had a 9 o’clock curfew, you were encouraged to not have friends over. You weren’t really allowed to leave unless it was, like, a family holiday.”

Credit: Matt Baron/Shutterstock

Sex With Hef

When Marquardt asked Madison to confirm that sex with Hefner lasted “no more than a minute,” she said that said on “Juicy Scoop” with Heather McDonald in August 2022 that she “blocked it” out, adding, “Everybody's just trying to get it done as quickly as possible.”

Credit: Shutterstock

Watching ‘Secrets of Playboy’

“They did 12 episodes. I watched all of them except episode two. I don’t want to watch myself talk about my trauma again. I can’t take it. But every other episode, I watched — and it came out over the course of 12 weeks. I had nightmares after I watched them,” Madison said in August 2022. “I had a nightmare I was back at the mansion every single night after Secrets of Playboy.”