The late Playboy founder lived in the storied Playboy Mansion, located in the Holmby Hills area from 1974 until his death aged 91 in 1997. The imposing abode was the venue of countless parties and celebrity gatherings over the decades.
Madison, who lived in Hefner’s home for several years until she parted ways with the publishing mogul in 2008, spoke about attending the annual Playboy Jazz Festival at the Hollywood Bowl and recounted the traffic they often had to battle through.
“I think it’s funny because we refer to going to the Hollywood Bowl as traveling,” Madison said to her former Girls Next Door co-star Bridget Marquardt on the latest episode of their Girls Next Level podcast. “And I think that shows just how insular our little world was.
“When there’s an event at the Hollywood Bowl you don’t even want to drive by there, because traffic is so bad with everybody trying to get into the parking lot.”
“The Playboy Mansion was like over near Bel Air, like over more on the Westside,” Madison said of the house, which is approximately eight miles away from the Hollywood Bowl. “So anytime we would drive—which wasn’t often—to Hollywood, it just felt like a big excursion.
“I remember the other long drive we would do was to go to a [Los Angeles] Lakers game once a year. We would always cut across using Olympic [Boulevard], and we would pass by some residential houses and every single time we would go, Hef would look out the window and be like, ‘Itty-bitty houses, for itty-bitty people.’ He said that every time.”
Marquardt, who along with Kendra Wilkinson lived with Hefner at the same time as Madison, chimed in: “I’d be like, ‘Wait, these are just regular houses for regular people. What are you talking about? This is normal. Not itty-bitty at all.’”
Madison, 42, and Marquardt, 48, have been using their podcast to extensively recount their experiences living at the Playboy Mansion with Hefner.
During a podcast episode back in August, Madison said that the first time she and Hefner had an intimate experience, it occurred while she was “really wasted.”
Madison recounted how in the early 2000s she and partied at former Hollywood hotspot Las Palmas with Hefner and a group of other women that included a so-called “recruiter” and a fellow new arrival to the fold.
The model spoke about how she drank copious amounts of vodka to ease her nerves as she essentially auditioned her way into his life. Madison told how she was so inebriated that she has little recollection of their bedroom encounter.
“I don’t even remember what happened the rest of the night,” she said. “The next thing I remember was that Hef was telling the recruiter, ‘Get her a pair of pink pajamas and she’ll stay in your room tonight.’ And then I just like stumbled out of there and she handed me a pair of pink pajamas.”
Hefner passed away in 2017 at the age of 91. In the years since his death, a number of people have spoken of darker experiences in the Playboy empire.
Madison previously opened up about life in the Playboy Mansion in her 2015 memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
“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 residence. “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.”
Newsweek has reached out to Hefner’s estate for comment.