The 42-year-old, who dated the late Playboy founder from 2001 to 2008, spoke candidly about her experiences while living in the Beverly Hills home during an episode of the Ahead of the Curve with Coco Mocoe podcast, which aired on 11 September. During the conversation, host Coco Mocoe asked Madison if she knew where Hefner’s controversial feelings about red lipstick “stemmed from”.
In response, Madison claimed that his hatred for the makeup was “a control tactic,” before alleging that Hefner didn’t initially take issue with her wearing lipstick when she first moved into the mansion.
“When I was brand new, I wore red lipstick out a couple of times and he didn’t say anything about it,” she claimed. “Because when you were the new girl in the group you were always treated well.”
She then recalled a phrase she once heard from someone about cults, reciting: “The higher up you are in a cult, the worse you’re treated.” She added that these people were treated worse because leaders “want the new people to bond and feel into” the cult.
Madison claimed that after living in the home for “six months”, Hefner took issue with her wearing red lipstick. She noted that at the time, she was “living in [Hefner’s] bedroom” and “was his main girlfriend”.
She continued to describe how Hefner reacted her wearing red lipstick, claiming that he believed makeup didn’t make the playmates look “young enough”.
“He felt like he had the leeway to yell at me over it,” she said, referring to her decision to wear red lipstick. “I think he didn’t love it because when he invented the concept of a playmate in the ‘50s, he wanted the women to look very young and fresh faced.”
She went on to allege that Hefner wanted his playmates to look young, as he described women in the “50s, at the time,” as “somebody’s older sister”.
“It was more sophisticated, fashion model, red lipstick,” she said, describing women’s appearances in the 1950s. “It was like a lot of fabric and big skirts and everything and he hated that. He wanted skimpy and fresh-faced and very young looking.”
Madison also emphasised her belief that Hefner’s “hatred for red lipstick” came from the fifties, a time he allegedly associated with “an older mature woman” and not with the “barely legal thing anymore”, seemingly referring to the young ages of his playmates.
Madison isn’t the first former playmate to make claims about Hefner’s hatred towards red lipstick. In A&E’s 2021 docuseries, Secrets of Playboy, Hefner’s ex-girlfriend, Bridget Marquardt, claimed that he’d get upset if Madison wore red lipstick. She also alleged that while Hefner took issue with Madison wearing the lipstick, he didn’t seem to care when other playmates did.
“Hef would be pretty abrasive in the way he said things to Holly,” Marquardt explained. “She had red lipstick one time and he flipped out, said he hated red lipstick on girls, take it off right away. Even though other people could wear red lipstick and it didn’t seem to bother him.”
Elsewhere in the Secrets of Playboy docuseries, Madison described her time living in the mansion as “cult-like” and shared her perception of Hefner.
“The reason I think the mansion was very cult-like, looking back on it, is because we were all kind of gaslit and expected to think of Hef as, like, this really good guy,” she explained. “And you started to feel like, ‘Oh he’s not what they say in the media, he’s just a nice man.’”
Last month, Madison also opened up about the “toxic” body shaming that she experienced while living in the Playboy Mansion. During an episode of the Just Trish podcast, released on 10 August, she alleged that Hefner “liked his women very, very thin”, before scrutinising the “whole culture up there at the mansion” and describing how playmates were expected to look a certain way.
“Everybody’s beauty standard was kind of, oh women are supposed to be really young and really thin and really in shape,” Madison said. “And if she’s not in shape, she’s not doing it right. That was the kind of feel you got from people in general, in that whole society.”