Holly Madison Spills on the Creepiest Playboy Mansion Ritual That’ll Make You Question Everything You Thought You Knew About Hef’s Kingdom
Added on May 6, 2025 inCelebrity News Cards
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Ever wonder what it’s like to live inside a real-life episode of The Twilight Zone—but the mansion is Playboy’s, and the star? Hugh Hefner himself. Holly Madison, who dated Hef from 2001 to 2008, just peeled back the curtain on some truly bizarre “bedtime rituals” that went down in the infamous Playboy Mansion. And with the Moon hanging heavy in Scorpio today, stirring all things secretive and intense, it’s the perfect cosmic backdrop to dive into the shadowy, uncomfortable truths behind the mansion’s glamorous facade. Imagine suiting up in matching flannel pajamas, nursing a belly full of vodka, only to “perform” a nightly routine no one really wanted to be part of—talk about a ritual that screams “fake it ’til you make it.” Holly’s recollections aren’t just tales from the past; they’re a stark reminder of how power dynamics can turn even the most glittering places into shadowlands. Curious to know what really happened behind those velvet ropes?
Holly Madison opened up about the bizarre rituals she experienced while living with Hugh Hefner.
The 45-year-old dated Hef in her late 20s from 2001 to 2008, shacking up in the notorious Playboy Mansion.
Over the years, and particularly since the editor-in-chief’s death in 2017, many former Bunnies, partners and girlfriends have spoken out about their time in the ‘dirty’ house.
And while she now hosts the latest season of The Playboy Murders, she wrote in her 2015 book Down the Rabbit Hole about her time in with Hefner in the Mansion.
This includes her discussing the ‘bedtime ritual’ which the girlfriends in the house were expected to take part in.
“I didn’t immediately realise that all girlfriends were required to sleep with Hef,” she wrote.
Holly Madison lived in the Playboy Mansion in the 00s (Raymond Hall/GC Images)
Madison said that while in a limo back with the girlfriends, one of them explained to her that all of them were ‘expected to join Hef in his bedroom’.
She claimed that they ‘all hated’ this routine and would try and ‘get it over with as quickly as possible’.
She said this ritual before bedtime would happen biweekly as another girlfriend apparently advised her to just ‘fake the f**k’.
Madison added that they would all get dressed into identical flannel pyjamas before the ‘bedtime routine’ and on her first time there was ‘roughly a third of a bottle of vodka sloshing around in my stomach’.
And as the ritual played out around him, according to Madison, Hef would watch porn, smoke a joint of weed and w**k while the women in the room ‘pretended’ to get off and ‘put on a show’.
“No one,” she wrote. “Was actually in the mood (besides Hef, I assumed) or turned on in the slightest. Like the porn itself, it was all just for show.”
She recalled on her first time that her ‘turn was over just as quickly as it started’.
Madison would partake in Hef’s ‘bedtime routine’ (Michael Loccisano/FilmMagic)
“I have never had a more disconnected experience,” Madison said in her memoir. “There was zero intimacy involved. No kissing, nothing. It was so brief that I can’t even recall what it felt like beyond having a heavy body on top of mine.”
The morning after her ‘first bedroom experience’, she said she felt ‘damaged and affected’ but the shame in herself spurred her on to ask to move in.
“After disappointing myself like that, I had to come away with something positive, something to make it right in my mind, somehow,” Madison explained. “I knew that if I couldn’t find a silver lining, I couldn’t forgive myself for the night before.”
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