The Playboy Mansion has long been wrapped in myth, fascination, and carefully curated fantasy. Films, documentaries, and television series have tried to capture what life inside its walls was really like, but for years, the truth remained largely limited to those who actually lived there.
Now, one former resident is speaking candidly about her experience.
Holly Madison, 45, who was in a relationship with Playboy founder Hugh Hefner for several years, recently appeared on a podcast hosted by Owen Thiele, where she opened up about her private life at the mansion—sharing details that challenge many long-held assumptions.
During the conversation, Madison addressed her sex life with Hefner, drawing a clear distinction between private moments and those that involved others.
“Well, it’s a very different story between when we were just by ourselves than with everybody else in the room,” she explained.
When the topic turned to group sex—an element often associated with the Playboy Mansion—Madison was blunt about her feelings.“Everybody else in the room, no,” she said. “That was disgusting. I hated it. I made it very known I hated it.”
Madison has previously spoken about feeling pressured into those situations, and she reiterated that discomfort during the podcast, making it clear that those experiences were among the most negative aspects of her time there.
She also addressed the much-discussed 53-year age gap between herself and Hefner, pushing back against assumptions that it defined their intimacy.
“If it was just me and him, it was a lot more normal than you would think,” she said.
Podcast host Owen Thiele admitted he found that surprising, given the public perception of the relationship. Madison responded with humor and frustration, noting how often online commentary focused crudely on Hefner’s age.
“There was a time when I couldn’t post anything without some dumb— in the comments being like, ‘Oh, old balls,’” she said. “Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”
She added that intimacy between them usually took place with the lights off, joking, “There’s a saying: ‘All cats are gray in the dark.’”
Madison and Hefner were together from 2001 to 2008. Hefner passed away in 2017 at the age of 91.
Beyond her relationship with Hefner, Madison also described some of the stranger, more unsettling details of daily life at the mansion. She recalled seeing trays placed throughout the property—in bathrooms, by the pool, and even near the tennis courts—stocked with items like tissues, Pepto Bismol, Vaseline, baby oil, and sunscreen.
“It was weird,” she said, describing the setup as unsettling rather than glamorous.
Despite these experiences, Madison was careful to clarify that her feelings about Playboy itself are complex and not entirely negative. Much of her criticism, she explained, is rooted in relationship dynamics rather than the brand or the work.
“My experiences that played with the negative parts of it are more related to the relationship and the relationship dynamics, both with Hef and some of the other girls,” she said.
In contrast, she spoke positively about her professional work with Playboy, emphasizing that posing for the magazine was something she genuinely enjoyed.
“I 100 percent enjoyed posing for the magazine,” Madison said. “I was always a fan of the pictorials. I always wanted to be in Playboy.”
She also worked behind the scenes at the Playboy studio, helping produce Playmate pictorials—an experience she described as “super fun” and creatively fulfilling.
For Madison, her time at the Playboy Mansion isn’t a simple story of glamour or trauma. It’s layered, contradictory, and deeply personal—marked by moments of opportunity, discomfort, empowerment, and pressure.
As she continues to speak openly about that chapter of her life, her reflections offer a more nuanced look at a world that was often reduced to fantasy from the outside.
