Holly Madison recalls Playboy founder Hugh Hefner's 'insecurities': 'He had a jealous streak'
Holly Madison, a former Playboy model and reality TV star, was 21 when she moved into the Playboy Mansion. She was Hugh Hefner's girlfriend from 2001 to 2008.
Holly Madison lived at the Playboy Mansion for nearly a decade – but for the model, life was far from glamorous.
The former Playboy pinup and "Girls Next Door" star has spent the last several years hopping down the rabbit hole of her life story and Hugh Hefner’s empire.
The model is returning for Season 2 of Investigation Discovery's (ID) true-crime series, "The Playboy Murders," which looks at high-profile tragedies associated with the iconic magazine brand. She’s also hosting a new series, "Lethally Blonde" in March, which promises to expose "the dark side of people pursuing beauty and fame."
"I think people are really curious about the [Playboy] world," the 44-year-old told Fox News Digital. "Even though there were a lot of negative experiences attached to it, I think for better or worse, that’s what I was put here to experience – [to] come out on the other side and tell people about it."
"I do look back, and I wish there were little ways I could have done it differently," she admitted. "But you never know. If I had stuck up for myself more, had more of a voice back then, I probably wouldn’t have lasted there. So I don’t think there’s any winning when it comes to that. I can’t really say I have any regrets, but would I want to go back and relive it? No."
Madison was 21 years old when she moved into the Holmby Hills home. She was Hefner’s girlfriend from 2001 to 2008. Even though the magazine mogul had multiple girlfriends – at one point, as many as seven, he had "a jealous streak," Madison alleged.
"Even though Hef was dating multiple people, I think it was really important to him and his image that he was seen as somebody who these women were completely devoted to," she explained. "He had a jealous streak. If he found out that one of his girlfriends was being seen with another man, that would really set him off."
"That’s why I saw some girls get kicked out and [get] banned from working for the company," she added.
The Playboy Mansion, once a celebrity hot spot, was known for hosting countless parties. In the property’s infamous Grotto, or the steamy cave-like pool, there were numerous debauched escapades.
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Madison alleged that as one of Hefner’s girlfriends, there were strict rules to follow, including maintaining a no-nonsense 9 p.m. curfew. She insisted that Hefner was plagued with "insecurities" to maintain his image as a pipe-smoking hedonist.
"He’d just gotten out of a marriage that he didn’t feel great about for whatever reason," Madison explained. "So he wanted to surround himself with multiple women and not just get hung up on one person. And I think he liked the attention he got when he was with three beautiful women on his arm, two of them who were identical twins. He always loved the attention and always wanted to be relevant and chase that kind of thing… And then when those three moved on, he went on to have seven girlfriends because how do you top dating twins?"
"Anytime a woman would feel independent enough that she would want to leave and move on to the next thing, he felt burned by it," Madison shared. "And things got stricter and stricter as time went on… I was not allowed to spend one night away until much, much later when we started doing ‘Girls Next Door.’ And that wasn’t even until Season 3. We were allowed to go on an overnight trip to learn how to snowboard. And because I’m going with security and cameras, he was OK with it for one day. But for most of my seven years with him, we were not apart for maybe more than two or three days."
Madison alleged that all of Hefner’s girlfriends had to maintain a certain look, and they couldn’t date other men or have an apartment of their own. If anyone broke a house rule, they would be shown the door. The greatest sin any girlfriend could commit was to be seen with another man, the series claimed.
"When I first moved in, I saw multiple girls get kicked out really abruptly, literally had their things packed and set out by the back gate," she claimed. "They were banned from any other event or working for Playboy again. So I was scared of breaking a rule. I was always walking… on eggshells and just didn’t want to get kicked back out on the street where I didn’t really know anybody in LA at that time and didn’t have a lot of resources. So for me, it was kind of… living in fear… just always wanting to do the perfect thing and never make anybody mad."
Madison alleged that she developed body dysmorphia due to Hefner’s constant judgment. It’s still something she struggles with today. And in a "high-stakes environment," the girlfriends were competitive against each other in hopes of becoming "the favorite."
"It was a lot of control," she said about living at the Playboy Mansion. "A lot of being made to feel insecure, a lot of being put down. But… you don’t want to be kicked out, and you don’t want to p--- anybody off. I feel like even people who were going to parties at the mansion felt like they knew Hef… [but] they didn’t necessarily see that side."
"I was a regular guest for the Sunday pool parties for probably a good year before I moved in," she continued. "And the reason I thought it would be a good idea to move [was] because… I saw that level of access [and] what looked like the nicest guy who was so generous, so great with his friends. He was great with some people. But with me, it was a very different story."
In 2016, Madison wrote a memoir, "Down the Rabbit Hole," where she alleged years of verbal and emotional abuse during her time at the Playboy Mansion. Then in late 2021, she described her "traumatic" first sexual encounter with Hefner in the podcast "Power: Hugh Hefner." And in early 2022, she sat down for A&E’s "The Secrets of Playboy," where she alleged the mansion was "cult-like."
The late magazine mogul's son, Cooper Hefner, spoke out ahead of A&E's premiere.
"Some may not approve of the life my Dad chose, but my father was not a liar," the 32-year-old tweeted. "However unconventional, he was sincere in his approach and lived honestly. He was generous in nature and cared deeply for people. These salacious stories are a case study of regret becoming revenge."
A spokesperson for Playboy also issued a statement to Fox News Digital.
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"Today’s Playboy is not Hugh Hefner’s Playboy," the statement began. "We trust and validate these women and their stories, and we strongly support those individuals who have come forward to share their experiences. As a brand with sex positivity at its core, we believe safety, security and accountability are paramount."
"The most important thing we can do right now is actively listen and learn from their experiences," it added. "We will never be afraid to confront the parts of our legacy as a company that do not reflect our values today.
"As an organization with a more than 80% female workforce, we are committed to our ongoing evolution as a company and to driving positive change for our communities."
Hefner died in 2017 at age 91.
Today, Madison said she feels at peace speaking about her past, as well as sharing the stories of other women who struggled at the Playboy Mansion.
"It feels really good being out here doing it on my own and not having to look at my watch and be in by 9 every night," she said. "When I do that now, it’s to make sure my kids are in bed."