The show gave viewers a behind-the-scenes look into Hugh's personal life and each of his relationships with his girlfriends, as well as their relationships with each other. After the show went off the air in 2009, major bombshells about the lives of the girlfriends, Hugh and the Playboy Mansion were revealed.
So in celebration of E! Stars: Where Are They Now Week we're looking back at all of the bombshells that have been dropped by Holly, Kendra and Bridget over the years. Check them out below!
1. Kendra "Didn't Know Sex Was Involved" in the Relationship With Hefner:
While on the reality show I'm a Celebrity, Get Me Out of Here Kendra revealed she "didn't know that sex was involved" with being Hefner's girlfriend.
She explained, "Hef asked me to be one of his girlfriends and live in the mansion. I'm like, I don't even know what that means, but hell yeah! I'm there! I was living in this small-ass apartment with this ugly-ass b--tch—I was praying for anything to get me out of there."
Kendra went on to reveal, "I moved in and weeks went by and I didn't know that sex was involved."
British TV presenter Melanie Sykes asked Kendra, "So, how does that conversation come about?"
"He was like, 'Do you want to come upstairs?' And I was 'Sure, let's have fun.'"
2. Kendra & Hef's Relationship Ended When She Became Engaged:
Kendra also revealed on the show that her relationship with Hefner ended in 2009 when she became engaged to Hank Baskett.
"You know, I did have relationships of my own, and I came back to the mansion one day, and I'm like, 'Hef, look! I got engaged!' And he's like, 'Congratulations!'"
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1. Holly Claims Hef Once Offered Her Drugs:
In her 2015 memoir Down the Rabbi Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Holly wrote that Hef offered her drugs during one of their first interactions at a LA nightclub.
Holly wrote, "'Would you like a Quaalude?' Hef asked, leaning toward crumpled tissue."
When Holly declined the drugs she writes that he replied, "'OK, that's good,' he said, nonchalantly. 'Usually, I don't approve of drugs, but you know, in the '70s they used to call these pills thigh openers.'"
2. She Claims Hef Tried to "Buy" Her So She Wouldn't Leave the Mansion:
After being accused of cheating on Hef with Criss Angel in 2008, Holly wanted to leave the mansion and she claims Hef tried to "buy" her with his will.
Holly wrote in the book, "It was there, in black and white. The will stated that $3,000,000 would be bestowed to Holly Madison at the time of his death (provided I still lived at the Mansion). At the time, it was more money than I'd ever know what to do with. . . . But I didn't want it. I actually pitied him for stooping to that level. I couldn't help but be offended. Did he really think he could buy me? I put the folder back on the bed just as I had found it and never breathed a word of it."
3. Holly Reveals She Contemplated Suicide While Living at the Mansion:
In the book Holly wrote that she "couldn't take" the "misery" anymore and recalled that while taking a bath in 2002 she thought, "If I just put my head under water and take a deep breath in, it would all be over."
4. Holly Accused Hef of "Talking Down" to His Girlfriends:
In Holly's second book The Vegas Diaries Holly wrote, "If Hef truly was confused as to why I left and forgot there was any fighting, he either had the world's most selective memory or thought talking down to his girlfriends and making them cry on a regular basis was normal."
5. Holly Believed Hef Only Knew "Roughly Four Things" About His Girlfriends:
In The Vegas Diaries she wrote, "He knew roughly four things about each girl. Her name, her age, where (approximately) she was from, and how well she behaved and followed the rules."
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1. Bridget Met Her Fiancé at the Playboy Mansion:
Bridget hasn't spoken out too much about her time at the Playboy Mansion but she did recently reveal that she met her now-fiancé Nick Carpenter while she was dating Hef!
While on Hollywood Today Live Bridget explained, "His grandfather was Hal Roach and Hal Roach was the creator of The Little Rascals, he did Of Mice and Men, Laurel and Hardy…that's one of the original Hollywood pioneers. And Hef was screening Of Mice and Men that night and the film historian, he always tries to bring something in that relates to the film and he brought in Nick, the grandson of Hal Roach."
And while Bridget admits she thought he was "really cute" she was still dating Hef. But at the time she was actually producing a horror movie and Nick's a director so they started working together a few months later. At that time Bridget admits she was already "one foot out the door" at the mansion so that's when she and Nick's romance started.