The allure of the Playboy Mansion has long captured the public’s imagination, with numerous movies and TV shows attempting to depict the glamour and mystery inside its walls.
Yet, the actual experiences of those who lived there—especially during Hugh Hefner’s reign—remain largely untold. One former resident is now shedding light on what life was truly like.
Keep reading for more insights.
Holly Madison, now 45, once dated the Playboy founder and recently spoke candidly about her past during a podcast interview with Owen Thiele.
The ex-Playboy model didn’t shy away from sharing intimate details of her relationship with Hefner, particularly their sex life. “Things were very different when it was just the two of us,” she admitted.
Madison revealed her strong aversion to group encounters, a common occurrence at the Mansion. “That was gross. I hated it. And I made sure everyone knew I hated it,” she said, referring to group sex sessions she reluctantly took part in.
She also addressed the significant age difference between her and Hefner—53 years—but said it didn’t affect their private moments. “When it was just me and him, it felt surprisingly normal,” she explained. Hefner passed away in 2017 at the age of 91.
Thiele was taken aback by her claim of normalcy despite the massive age gap. Madison replied, “No one believes me.”
She also discussed how online trolls would mock their relationship. “I couldn’t post anything without someone commenting, ‘Old balls,’” she recalled. “Maybe that’s true for some people, but I never saw anything like that,” she added humorously.
Madison noted that intimacy with Hefner always took place in the dark. “You know what they say, ‘All cats are gray in the dark,’” she quipped.
Their relationship lasted from 2001 to 2008. Madison has previously spoken about feeling coerced into group sex and witnessing unusual practices at the Mansion. She described bizarre items scattered throughout the property—trays filled with Kleenex, Vaseline, Pepto Bismol, baby oil, and sunscreen—essentially, improvised lubricants. “It was strange,” she said.
Reflecting on her time there, Madison said the more troubling aspects stemmed from interpersonal dynamics rather than her actual job. “The toxic parts were more about my relationship with Hef and some of the other women,” she clarified.
However, she emphasized that her work with Playboy was something she genuinely enjoyed. “I absolutely loved doing photo shoots. I was a big fan of the magazine and always dreamed of being part of it. I even helped produce Playmate pictorials at the studio for a few years, and that was an amazing experience.”
Ultimately, Holly Madison is offering a nuanced account of her years in the Playboy Mansion—highlighting both the highs and the deeply uncomfortable lows.
What are your thoughts on her revelations?