Crystal Hefner, Kendra Wilkinson and Holly Madison lived a strange life of decadence and fantasy while living at the Playboy Mansion in the last years of Playboy founder Hugh Hefner’s life.
And while Hefner once requested his now-widow Crystal “only say good things about me,” seven years after his death, his former wife and girlfriends are speaking out about the reality of life behind those gilded gates.
Crystal, 37, who married Hefner in 2012 and stayed with him until his death at 91 in 2017, revealed to People magazine this week that while she loved the magazine founder, she was never “in love” with him.
Crystal said she initially had misgivings about marrying him after he proposed, but eventually returned to him after a brief relationship with Jordan McGraw, Dr. Phil’s son.
From left: Crystal Hefner, Kendra Wilkinson and Holly Madison have all demystified the time they spent at the Playboy Mansion. (Getty Images)
“I realized I was dealing with a really big power imbalance,” she said of Hefner. “It seemed like a world of success and fantasy, but everyone’s having to sleep with an 80-year-old. There’s a price. Everything has a price.”
Although the historic Playboy Mansion looked luxurious, Crystal says the Gothic-Tudor home built in 1927 had grown “run-down” while she was living there after years of “too many parties.”
“This place doesn’t really get cleaned that well and there’s mold, and it just felt just kind of run down and gross after a while,” the 37-year-old told People magazine of the mansion nestled in the Holmby Hills neighborhood of Los Angeles, which Hefner bought in 1971. “Too, too many parties. It was worn out.”
Crystal added that the exotic animals that lived on the grounds didn’t seem well cared for.
Crystal with Hugh Hefner in 2014. (Charley Gallay/Getty Images for Playboy)
“I feel like I was constantly crying for everything and everybody there,” she told the magazine. “All those animals were so depressed and sad-looking. It was all an illusion. I don’t even know if I was happy, to be honest.”
Crystal said Hefner would give the girls who lived at the mansion an allowance each week that he expected them to spend on their appearance, but he was also very controlling about how they looked.
“Our nail polish couldn’t be anything but some neutral color, no French manicure,” she told People, adding that he would stipulate, “Don’t have a belly button ring because that’s trashy.”
The couple got engaged in 2010. (Gregg DeGuire/FilmMagic)
Hefner didn’t like it when Crystal’s dark roots started to show, “so, I’d have to go bleach it, and it would burn my scalp, and I’d have blisters,” she said. “But for some reason I thought this was all normal and that’s what it meant to be seen as beautiful in Hef’s eyes.”
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“At the time, I thought I was on top,” Crystal told People about when she first went to the Playboy mansion in 2008.
She added, “I thought, wow, if I just like everything that he likes and do all the things that he wants me to do, then I’m the favorite. And I was, but I just lost myself in the process.”
Kendra Wilkinson
Kendra Wilkinson, who became one of Hefner’s girlfriends on E!’s “The Girls Next Door” reality show when she was 18, told People this month, “I’ve had to face my demons. Playboy really messed my whole life up.”
Kendra Wilkinson with Hefner in 2009. (Denise Truscello/WireImage)
She added, reflecting on her time there 20 years ago, “Time really does do a lot of weird things. You go through time and perspectives start to change. Your ideas start to change about ‘Why?’”
Wilkinson continued, “You start asking why. ‘Why did I do that? ‘Why did I have sex with a 90-year-old man at that age?’ ‘Why did I do that?’ ‘Why did I go to the mansion in the first place?’ ‘Why did I get boobs?’ ‘Why did I bleach blonde my hair to be like?’ … I was going down this crazy regretful path that I don’t think I needed to do.”
She said “that’s not who I am anymore” and hoped people in the world of her new career in real estate wouldn’t judge her. “I’m a single mom of two, like I’m starting a new business. Those were different times. They were like my wild twenties.”
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“I respect what they’ve been through,” Wilkinson said of fellow former girlfriends Holly Madison and Bridget Marquardt, with whom she co-starred on “The Girls Next Door.” “I respect their stories. My story’s a little bit different. I was very young. I was actually younger than them moving in, but I don’t regret it.”
Wilkinson said she never saw anything during her time at the mansion that felt “harmful” to her.
“Even though having sex with an older man, if that’s harmful, then sure,” she continued. “But in my perspective, I never really saw anything that was out to get me or was out to hurt me. Hef was never really my boyfriend. I was at the Playboy Mansion for the sake of partying. That’s what I was there for.”
Holly Madison
Holly Madison was Hefner’s main girlfriend while she lived at the mansion. (Denise Truscello/WireImage)
Holly Madison dated Hefner from 2001 to 2008. During her time at the mansion, Madison claimed there were many times when she wanted to leave. In 2008, after wrapping five seasons of “The Girls Next Door,” she finally left the Playboy Mansion.
In 2016, the former Playboy Bunny wrote a memoir titled “Down the Rabbit Hole,” hi which she alleged years of verbal and emotional abuse. Then in late 2021, the former “Girls Next Door” star described her “traumatic” first sexual encounter with Hefner in the podcast “Power: Hugh Hefner.” In early 2022, she sat down with A&E for “The Secrets of Playboy,” in which she alleged the iconic Playboy Mansion was “cult-like.”
“I would definitely say that living in the mansion created a body dysmorphia for me because I was always kind of wondering what’s wrong with me,” Madison, who moved into the mansion when she was 21, told People in November.
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She said Hefner “had a way of making me feel like I wasn’t pretty enough, and I would look around to everybody else and constantly be wondering, what’s so different about them and why are they so much better?”
Fox News Digital’s Stephanie Giang-Paunon contributed to this report.
