Everything We Know About Life in the Playboy Mansion, from Holly Madison and Kendra Wilkinson's Memoirs

In the wake of Hugh Hefner's passing, we're looking back on what two of his most famous girlfriends had to say about life with him in the Playboy Mansion

Holly Madison is not afraid to speak out about her years as a Playboy bunny.

“It was a constant struggle,” Madison told PEOPLE of her seven years living at the Playboy Mansion with former boyfriend Hugh Hefner. “I was trying to sell this image of ‘Oh everything is so great here,’ but I was miserable inside.”

Former The Girls Next Door stars Kendra Wilkinson and Madison fell out years ago, but both have spoken out about their experiences. In 2015, Madison published a juicy tell-all memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, which Wilkinson accused of being a “re-writing of history.”

Steven Lawton/Filmmagic

What was life really like in the mansion?

We’re taking a break from the she-said-she-said to focus on some other telling words: Here, compare Wilkinson’s memoir from 2011, Sliding into Home, to Madison’s Down the Rabbit Hole.

1. On sex …

Holly: “Vicky [another one of Hef’s girlfriends] was eager to bring as many girls up into the bedroom as possible. I could guess her reasoning: the more options Hef had, the less likely she’d be called to duty. It seemed to me that she made it her mission to lure every new Playmate up to the bedroom to pay their dues. In those first few years, I would say the majority of the Playmates eventually selected had found their way into Hef’s bedroom. I guess Vicky figured that if she had to sleep with Hef, they should all have to sleep with him.”

Kendra: “I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it.”

2. On the show …

Holly: “We were constantly reminded that the show was Hef‘s show – our contributions were irrelevant. We were the decorative icing, not the cake. According to our boyfriend, he could have splashed any three blondes on-screen and found instant success.”

Kendra: “The crazy thing about television is that you are rarely allowed to grow. You are molded into a character based on some of your strongest traits, and you are forced to stay that way for your entire television life.”


3. On Hugh Hefner

Holly: “That’s how disagreements always ended with Hef; he would just stomp off, and you were left to pick the pieces of your self-worth up off the floor. I’d invested every part of myself in the mansion and had nothing waiting for me outside those gates. I felt so trapped and so vulnerable to his criticisms.”

Kendra: “Staring into his eyes, I didn’t see a man four times my age with ten times more girlfriends than most. Even though I hardly knew him yet, I saw a sweet man who made me feel really good about myself – a true gentleman. It was weird, but in my heart, I felt like he was someone I could possibly trust.”

4. On relationships with the other Bunnies

Holly: “Leaving the other girls in her wake, Vicky charged up to my side of the bed, her nostrils flaring like an enraged bull and her fists clenched at her side. She came on so aggressively I worried she might hit me. It wasn’t out of the question. I’d seen some girlfriends resort to throwing punches over things as trivial as someone cutting the bathroom line at a nightclub.”

Kendra: “During that first season, Bridget, Holly, and I continued to keep our distance, except when we were filming. We did our thing off camera, and there was an unspoken competition for camera time when the cameras were around. Each of us wanted the others to look good and be successful, but whether they will admit it or not, I think we each wanted the spotlight and to look the best in every episode.”

Holly Madison Fires Back at Kendra Wilkinson: ‘Hef Actually Did Put Me in His Will and I Left’

6. On jealousy

Holly: “Suddenly, Playmates who had once mocked me were kissing my ass, bringing me gifts and showering me with compliments now that I was Hef’s No. 1 girlfriend. The sudden shift in the way some of those girls acted was completely obvious and shameless, but I suppose they thought I was too dumb to notice or that I would be so grateful to be treated kindly for a change that I wouldn’t object.”

Kendra: “Nights were hard because while my Playmate friends got to go out and party, I would have to be home by 9 p.m. I’d get a text message from a girl that read, ‘Having so much fun in Vegas. Wish you were here! Partying with all these football players,’ and that was devastating. I felt so trapped and angry when I was missing out on something good.”

Hugh Hefner
Laurent Rebours/AP

7. On fame

Holly: “Like me, Marilyn [Monroe] had suffered at the hands of some not very nice men. She was used, unappreciated and struggled to find herself. She worked her way up in Hollywood with stars in her eyes and a kind heart, but found that Hollywood wasn’t always as kind in return. She may have been publicly adored, idolized and lusted after, but she felt alone and trapped.”

Kendra: “When you star in a reality show, the entire world thinks they know you. Fans see you as the girl next door, tabloid editors see you as a story line and paparazzi see you as a target. At the end of the day, they are all wrong.”

8. On physical appearances …

Holly: “‘Don’t ever wear red lipstick again,’ [Hefner] warned me in a low voice and turned toward the door He paused and turned back around to survey my reaction. Deciding he hadn’t done enough damage, he served me one final blow before storming out of the room: ‘You look old, hard and cheap.'”

Kendra: “One night, we were all in the limo on the way to a book signing with Hef when he pulled me aside. ‘Is everything okay?’ he asked. ‘I feel fat, Hef,’ I told him. ‘Everyone is so pretty. It’s making me really insecure.’ ‘Well, you look a little bigger,’ he said honestly. ‘Maybe you can go to the gym.’ When we got home, I went to my room and cried myself to sleep. I was disappointed in myself. I had this whole mansion and a great life to enjoy, and all I was doing was lying around and eating. I felt so lazy and miserable. This was supposed to be paradise, but for me, it wasn’t.”

Hugh Hefner-News
Yann Gamblin/Paris Match/Getty

9. On living in the mansion …

Holly: “The climate inside the mansion was toxic. I didn’t participate in the cocaine benders, the side boyfriends or all their harebrained moneymaking schemes that were all in direct violation of Hef’s rules. I rarely left the mansion, so making it home in time for curfew was never an issue either.”

Kendra: “Instead of me, Holly and Bridget wanted to bring in Audra, this girl who was looking to move into the mansion and become Hef’s girlfriend. She and I had issues – our personalities totally clashed – and she was trying desperately to take my place, and for some reason Holly and Bridget were on her side. They all had a pact that they were going to stick together and get rid of me. I don’t know why; I hadn’t done anything wrong. I’m tough, and I would never in a million years have let them know it, but it hurt my feelings.”

10. On dating other men …

Holly: “How these ‘side boyfriends’ felt about their girlfriends dating Hugh Hefner, I don’t know. I imagine the girls weren’t forthcoming with these men and probably denied that they even had sex with Hef (they denied it to everyone). Most of them referred to ‘dating’ Hef as a big publicity stunt to help them launch their careers.”

Kendra: “After living in the mansion for a year, I did miss dating, and there were times when I was out during the day (before my 9 p.m. curfew) or at therapy school or even at Playboy parties where I met guys. It’s only natural. I needed to have my own life, or I would have gone crazy. But at the same time, I didn’t want to disrespect Hef or the Playboy name – that always came first.”

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