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.”
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.”
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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:
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