No Holding Back! Holly Madison's Craziest and Wildest Confessions About Hugh Hefner

Holly Madison has never fully escaped memories of Hugh Hefner and the Playboy Mansion.

The former Playboy Bunny appeared on the May 5 episode of the "Let's Be Honest With Kristin Cavallari" podcast, where she revealed the late Playboy founder "was not taking it seriously that [she] wanted to leave" the "cult-like mansion."

'"He would leave his will out on the bed on my side so I could see how much money was going to be left for me if I stayed…or after Kendra [Wilkinson] and I announced we were leaving, it was a big trend for tabloidy outlets to write like, 'Oh, these girls just aren't going to be famous anymore,'" she recalled. "So Hef would get all this stuff printed out and leave it out so I would see, hoping I would change my mind, like, oh my god, I can't be irrelevant. I must stay."

She also accused Hefner of creating a "super competitive" atmosphere among the girls living in the mansion, saying the late media mogul "liked to kind of play two different teams against each other."

"So he always felt fought over, and he could always get his way, and we couldn't unionize against him," Madison explained. "And I didn't realize that was going on. I thought he was so great, and I thought it was just the girls being awful…but also coming from myself and just the fear and pressures I had. Because I was just this random girl from Oregon who felt like, okay, I made this decision."

Madison stayed in the mansion for seven years, afraid to leave due to her fear she "was going to be judged so heavily for [her] choices."

Elsewhere in the podcast interview, Madison detailed the "compulsive" intimate routines she claimed she was "required" to participate in with Hefner.

"In the beginning, we would go out twice a week and it would always be after we went out. When the show started filming, we would stop and it was amazing," she said of filming the reality show Girls Next Door. "Not that we wouldn't ever go out if it was a special occasion, but we stopped those regular club nights where we would go out every Wednesday and Friday because we were so busy with the show."

The reality star said Hefner "loved" the show and "got high off" of it.

"It gave him new relevance like an ego boost, so he didn't really feel the need to do these compulsive s-- nights to make himself feel wanted," said Madison. "There was no discussion to stop the nights. It just evolved and we just didn't want to do it anymore."

Madison has been vocal about the "disgusting group s--" she and the other girlfriends experienced with Hefner.

"Well, it's a very different story between when we were just by ourselves than with everybody else in the room," she shared in a May 2025 episode of SiriusXM's "In Your Dreams" podcast. "Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it."

On the other hand, her one-on-one encounters with Hefner were reportedly "a lot more normal than you would think."

Madison's statement mirrored what she divulged on her "Girls Next Level" podcast, saying he "wouldn't move" like he was a "bump on the log in the middle of the bed."

"I can't explain to you guys how embarrassing that whole routine was. Especially as we got later down the road when there would be, like, a lot of conflict with the other girls," she added. "You're literally sitting there naked having s-- in front of a group of people who hate you and talk s--- about you while you're having s--, and you can hear it. It was just, like, h---."

In her memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Madison discussed the women's attempts to quickly finish their bedroom escapades with Hefner.

"When I think about it now, it's almost comical. Every red-blooded American male has no doubt fantasized about what went on in Hugh Hefner's bedroom with his harem of blond bombshells. The answer? Not a whole lot," she wrote.

Madison likened Playboy to Scientology, expressing how she felt like there was "kind of a cult mentality with a lot of people who surrounded" Hefner.

She told The New York Post that everyone regarded Hefner as "not human, and infallible," adding, "You can't even say — not even something bad, but you can even say something bad-adjacent about him without being like, excommunicated. In Scientology, they call it a suppressive person when someone goes against the church. And I kind of felt like I was treated that way."

Hefner's pad appeared less impressive than expected.

In a November 2024 episode of the "Girls Next Level" podcast, Madison and fellow former Playmate Bridget Marquardt recalled seeing mold, dust and junk all over Hefner's room, saying it was "just a disaster in there."

"The lights were out, but there were two giant TV screens in there that were playing p---…" said Marquardt. "There's just so much junk."

Madison agreed and labeled it "hoarder-style."

"Imagine thinking you're this big player and you're bringing all these girls home, and your room looks like s---," she added. "It's like the weird eccentric millionaire version of the guy with the mattress on the floor and a Pulp Fiction poster."

Madison spilled more tea about the mogul during an appearance on the "Ahead of the Curve" podcast with Coco Mocoe in 2023.

At the time, she disclosed the mogul "hated" when his girlfriends wore red lipstick.

"When I was brand new, I wore red lipstick out a couple of times, and he didn't say anything about it. Because when you were the new girl in the group you were always treated well," she explained. "So I would wear red lipstick when I was new, and it wasn't a big deal. Until like six months into it, when I was living in his bedroom, and I was the main girlfriend, and he felt like he had the leeway to yell at me over it."

The blonde beauty assumed Hefner "did not love it" because he had always wanted women to look "very young and fresh-faced" when he established the concept of a playmate.

"He felt like the look in the '50s at the time was very… He described it as 'somebody's older sister,'" she continued. "It was more sophisticated, fashion model, red lipstick. It was a lot of fabric and big skirts and everything, and he hated that. He wanted skimpy and fresh-faced and very young looking."

According to Madison, she and the other women around Hefner were never particularly concerned about accidentally getting pregnant during their bedroom activities.

"Not to be gross and graphic, but here we are. He never finished in anybody," she revealed on the "Girls Next Level" podcast. "And when I say that, I don't mean a last-minute pullout. I mean, he would do whatever on our bedroom nights, and then the last part of it would just be him j------ off watching [expletive]. Like, it wasn't even near anybody."

Madison also pointed out Hefner only ever had kids "when he was married and it was planned."

"So, he knew what he was doing in that respect," she noted.

In a 2022 episode of the podcast, Madison remembered how Hefner used baby oil during intercourse despite her refusal.

"I do not recommend this. It is an infection waiting to happen. It's disgusting," she underscored.

Per Madison, the product left her "constantly irritated" because it "throws off [women's] pH," leading to frequent yeast infections.

"I remember talking to the gynecologist about it and then telling Hef, 'You need to stop using the baby oil. I can't use it,' and even telling him the gynecologist agreed with me, and he would argue with me and be like, 'Well, people use baby oil on babies,'" she added. "And I'm like, 'Yeah, on their skin. Not internally. You're not supposed to put it there.'"

However, others later told her Hefner would apply the oil to her without her knowledge, describing the actions as "so foul and so nonconsensual and so gross."

Madison dropped a shocking bombshell in the premiere episode of her and Marquardt's podcast in August 2022, stating she and the other girls rushed through the experience because no one wanted to actually participate.

"We thought of it as a chore that we had to do or else we'll get kicked out of the house," she confessed.

In the "Power: Hugh Hefner" podcast, the Holly's World star alleged the late magazine publisher took nonconsensual nude photos of the women using a disposable camera.

"And these women were almost always intoxicated. I know I was—heavily intoxicated," she said. "When you would go out with Hef, he's taking all types of naked pictures of these women when they're wasted out of their minds. It's just gross."

Madison added Hefner would make copies of the pictures and distribute them to "everyone who had gone out that night."

"So if you were messed up and if you were in his bathtub with your top off and some other girl is doing some sexually explicit pose on you and he took a picture of that on his disposable camera, he'd make a copy and give it to everyone that night and put it in a scrapbook," she continued.

Madison revealed more behind-the-scenes details on the December 13, 2021, episode of the "Power: Hugh Hefner" podcast, including her "traumatic" first sexual encounter with Hefner.

"I was wasted," she said of the experience. "He was literally pushed on top of me. And after it happened, I was just mortified and embarrassed, and it had way more of an emotional impact on me than I thought it would."

She reportedly did not expect to have s-- that night and, instead, thought it would be more of a first date.

"I thought it would be more the type of thing where I saw what happened, saw what was going on. If I wasn't comfortable with it, I wouldn't have to do anything and I could make my decision on whether I wanted to come back for date No. 2 or not," said Madison.

The TV personality shared, "I thought he was really smart, I really looked up to him, so I liked him, and it wasn't that the idea of possibly having s-- with him repelled me so much — I know that's not relatable to a lot of people because they're like, 'Oh, he's an old man, gross.'"

"It was more the group aspect that was really out of my comfort zone and just the feeling of 'Wow, OK, that happened. Everybody knows it happened," Madison reflected on the disturbing encounter. "I kind of all of a sudden felt like everybody was going to know about me, and I was horrified by it."

After the jarring private moment, she reportedly felt it was time to ask Hefner if she could move into the Playboy Mansion.

"I felt like, 'There's no taking that back, so I might as well get what I came for,'" Madison elaborated. "I felt like by moving myself in and getting what I wanted from the situation, that was demanding respect in a way. I felt like if I didn't do that, I was just going to be haunted by this experience."

While on Alex Cooperon the "Call Her Daddy" podcast in 2021, Madison claimed she had to sleep with Hefner first before she was allowed to move into the property.

"I'm not trying to [expletive]-shame anybody or anything, but nobody ever got asked to move in unless they had slept with him," she said of the Playboy Bunnies' "requirement."