Every now and then, it's worth taking another dive down the rabbit hole.
Or at least that's how Holly Madison feels about her mid-00's E!'s series, The Girls Next Door, which featured her as Hugh Hefner's ever-doting, loyal wife-type figure alongisde the magazine mogul's other girlfriends Kendra Wilkinson and Bridget Marquardt.
"You can watch it two different ways," she recently explained to E! News’ Keltie Knight during an exclusive interview. "You can watch it for all the eye candy like the first time it came out and say, ‘Oh my God, look how fun.' Or you can watch it knowing about all the stuff going on behind the scenes, and that adds a whole other layer.”
Because in the years since the show wrapped it's six-season run in 2010, both she and Hugh's eventual wife Crystal Hefner have shared the less picture-perfect parts of their life with the late Playboy founder.
But when Holly, now 45, began visiting the infamous Playboy Mansion as a 20-year-old college student in Los Angeles, the aspiring actress—who would go on to become a bestselling author—thought it was an adventure worth hopping into.
There was a "spot open," she detailed on the Power: Hugh Hefner podcast in December 2021, with one of Hugh's previous girlfriends having decamped from the 22,000-square-foot manse.
"I wasn't necessarily expecting to have sex that night," she explained. "I thought it would be more of a first date."
Instead, she alleged, "He was literally pushed on top of me. And after it happened, I was just mortified and embarrassed and it had way more of an emotional impact on me than I thought it would."
Still, Holly reasoned, she "had always admired Hef" and "really looked up to him."
And, at that point, "I felt like there's no taking that back," she said, "so I might as well get what I came for."
Contrary to the jokes about their 53-year age difference, "It wasn't that the idea of possibly having sex with him repelled me so much," she explained. "It was more the group aspect that was really out of my comfort zone and just the feeling of like, 'Wow. That happened. Everybody knows it happened.'"
And she never fully got used to that dynamic.
"If it was just me and him, it was a lot more normal than you would think," Holly explained on the May 2 episode of Owen Thiele’s In Your Dreams podcast. But, "Everybody else in the room? No, that was disgusting. I hated it. I made it very known that I hated it."
Still, she did her best to play well with others.
No surprise, she and Bridget—her cohost on their Girls Next Level rewatch podcast—"have always been close," Holly shared when asked about the group dynamic during her 2021 appearance on Call Her Daddy. "We've always been friends since day one."
But when asked if she has a relationship with Kendra, Holly put things simply, "No."
As for the romance between her and Hugh, some aspects were actually quite average, Holly revealing how much of the time they had "boring basic sex."
And she remains relieved to this day that there were no huge surprises in that department.
"I knew it was because of him," she said of never getting pregnant with the businessman. "I was healthy. He was just too old."
And, yet, on Girls Next Door she not only expressed her desire to start a family with Hugh, but also made it clear that she needed a commitment in the form of a ring on the fourth finger of her left hand.
Ultimately, his refusal to wed for the third time coupled with their struggle to have kids was considered their breaking point. She called it quits in 2008.
"Holly wanted very much to get married and have children and that wasn't in the cards for us," Hugh shared in a video for Playboy at the time. "I made a noble effort on the children's part of it. I was not prepared at this point to marry again."
Until he was. Going on to date twins Kristina Shannon and Karissa Shannon along with Crystal, he eventually proposed to the latter, a onetime San Diego State psychology major, in December 2010.
"I'm very surprised," Holly told E! News after he got engaged to Crystal. "I have a lot of different feelings on it. I don't just feel one way. I kind of didn't want to put a generic statement out there like 'Congratulations!' because I felt everyone would see through that."
The eternal bachelor didn't have a smooth trip down the aisle however. Though his Playboy Playmate bride unexpectedly broke off their engagement five days before their vows, the two ultimately tied the knot in December 2012.
Holly would go on to wed businessman and producer Pasquale Rotella in 2013. They went on to welcome daughter Rainbow, 12, and son Forest, 8, yet, the couple filed for divorce just two weeks shy of their fifth anniversary.
But it was during her marriage to Pasquale that Holly was able to get enough distance from her life in the mansion to detail the experience in her no-holds-barred 2015 memoir Down the Rabbit Hole.
In print, Holly, who initially was under the impression the women did not actually have sex with Hugh, recalled her first night with him in vivid detail.
"Two huge television screens projecting graphic porn lit up the otherwise dark bed," she wrote. "In the middle, a very pale man was tending to his own business (if you're catching my thinly veiled innuendo) and puffing on a joint before passing it around to the nearest blonde. The girlfriends, in various stages of undress, were sitting in a semicircle at the edge of the bed—some kneeling, some standing, some lying down."
She alleged Hugh offered her a Quaalude and that this orgy-esque activity would take place twice a week.
"We would go out to the same club every Wednesday and Friday," Holly recalled in the 2022 A&E docuseries Secrets of Playboy, "and that would be expected when we got home."
In fact, much of her life was regimented.
Though she initially kept her one-day-a-week waitressing gig, it left Hugh feeling jealous, she claimed, so she eventually accepted his offer of a $1,000-a-week allowance instead.
She conformed to other ideals as well, alleging that he disapproved of her short haircut and called her "old, hard and cheap" when she wore red lipstick.
"You had a 9 o'clock curfew," she detailed on Secrets of Playboy of the cloistered existence. "You were encouraged to not have friends over. You weren't really allowed to leave unless it was like a family holiday."
And yet, "I tricked myself into thinking I had feelings for Hef," she wrote in the book. "He had this gentlemanly veneer, he was intelligent, and I loved watching old movies with him. I focused on the positive things, not the negative."
She was down the rabbit hole, she reasoned, and it'd be hard to climb out.
"Something happened in my mind that first night I had sex where I felt like, 'Ok I did that. I like breached my own boundaries and I wasn't comfortable with it. Now I have to make this situation into something,'" Holly explained on Call Her Daddy. "I almost locked myself into this box."
However, after suffering depression, suicidal thoughts, and—according to her—Hugh's accusations of infidelity, she'd had enough.
With Kendra coming to his defense, Hugh responded to the allegations Holly made in her book, suggesting she was simply seeking fame with her memoir.
"Over the course of my life I've had more than my fair share of romantic relationships with wonderful women," he told E! News in a statement at the time. "Many moved on to live happy, healthy and productive lives, and I'm pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can't win 'em all!"
While the two had their differing accounts of how their relationship played out, Holly wanted fans to know she wasn't pining for her old life.
"For so many years, I just wanted to move forward with positivity, only say nice things," she told E! News. "I wanted to stand on my own two feet, start from scratch, just be me, not talk about Hef. But, I would get so many people coming up to me saying, 'Don't you miss the mansion?' or 'I'm sorry Hef didn't marry you' and I'd see everything that was written about me and people think they know me just because they know one side of me from the TV show, which was seven years ago."
And while she wouldn't necessarily want to relive her past, "I learned so much," she told E! in 2024, "and I feel like my purpose here on earth is to share my story and help open people's minds to different perspectives."
(This story was originally published on Thursday, Sept. 28, 2017 at 1:09 a.m. PST)