Hugh Hefner’s 1 Requirement for Girlfriends Moving Into Playboy Mansion, Revealed

Holly Madison is a model, author, and pop culture personality who has been in the public eye for nearly twenty years. Madison first rose to fame in the reality television series The Girls Next Door, detailing her life as a Playboy bunny who lived in the Playboy Mansion with Hugh Hefner.

In recent years, Madison has made a name for herself as a host and Vegas entertainer, opening up to her fans regularly on her YouTube channel. As a mom of two young children, Madison has come a long way since her early days at the Playboy Mansion.

Recently, she chatted with the hosts of the “Call Her Daddy” podcast, detailing her time at the Mansion, and what Hefner’s requirements were for all the girls who moved in. 

How did Holly Madison become famous?

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Madison was born in Oregon in 1979. As a young woman, Madison was noted for her beauty and went on to work as a model and hostess to help pay for her college tuition.

Still, Madison had big dreams — and as she detailed in her memoir, she had early ambitions to become a star. “I dreamt of a world outside my little rain-suburban bubble,” Madison wrote. “I’d fantasize about a glamorous career and all the amazing costumes I would wear one day.”

Eventually, Madison began getting high-profile modeling gigs, and ultimately scored an invitation to the Playboy Mansion. She caught the eye of Playboy Magazine mogul, Hefner, and when she was 21 years old, she moved into the Playboy Mansion. 

Holly Madison was a high-profile member of the Playboy inner circle

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Madison made waves as one of Hefner’s girlfriends, and in 2003, she was cast in the reality television series The Girls Next Door. The reality series focused on Madison, as well as Hefner’s other girlfriends Kendra Wilkinson and Bridget Marquardt.

The series painted a rosy picture of the girls’ lives in the Mansion, often featuring footage of glamorous parties and events, including Playboy test shoots and birthday parties. Madison became a reality star and appeared on the show until 2009, when it went off the air, following the dissolution of Madison’s relationship with Hefner.

She went on to work on her own projects, including hosting gigs and burlesque shows. But to this day, fans have questions about Madison’s life at the Mansion and, more specifically, the details about her relationship with the much-older Hefner. 

What was Hugh Hefner’s requirement?

Hugh Hefner  poses for a photo on Nov 17 2005 in  Los Angeles, California.
Hugh Hefner | Dan Tuffs/Getty Images

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In a recent episode of “Call Her Daddy,” Madison talked about her relationship with Hefner, and the bizarre requirement that he laid out before Madison would be allowed to move into the Playboy Mansion.

“I had to sleep with him first,” Madison stated. “I’m not trying to slut-shame anybody or anything, but nobody ever got asked to move in unless they had slept with him.”

Madison’s account contradicts what other girlfriends of Hefner have said, including Kendra Wilkinson, who has stated in the past that she moved in with Hefner without first being intimate with him.

In her interview, Madison also revealed that she was grateful to have never gotten pregnant during her time at the Mansion, and that she is now happy to be free of the situation, admitting that by sleeping with Hefner, she had “breached her own boundaries.”