‘Secrets of Playboy’ Uncovers The Seedy Underbelly of Hugh Hefner’s Empire

Last summer, Holly Madison told me she used to hide in a secret bathroom in the Playboy Mansion when she needed a minute alone. We were talking about all the paranormal encounters she and Hef’s former girlfriend Bridget Marquardt had experienced while living in the mansion during the run of E!’s The Girls Next Door. “It was easy to feel creeped out in there,” she said of life in the mansion. “Not even in just a paranormal sense.”

The real horror of the Playboy mansion is the ghosts of the women who were under Hefner’s seductive reign of power – a legacy that still largely lores him as a staunch proponent of the free press, racial equality, and the sexual revolution. But there’s a dark underbelly to Playboy – a surface of which has only been scratched – until now.

In a new, 10-part A&E docuseries from filmmaker Alexandra Dean, who also made the Paris Hilton documentary This Is Paris, Dean interviewed more than 100 people, mainly women, who had been connected to Playboy in the last 60 years – to reveal a well deeper than the Legionnaires-infested waters of the mansion’s grotto hot tub of secrets of abuse and coercion.

“At the beginning, I thought I was doing a different sort of show. I was trying to unlock this Playboy world for you and take you through the richness of it and really there was a lot more looking at the culture of it,” Dean tells NYLON. “Overtime, as I began to form these relationships with the women, they began confessing things to me that really shocked me and it began to shift the story of what Playboy had really been.”

In her more than 100 interviews with former Playmates, Playboy bunnies, girlfriends, corporate employees, and those who worked and lived in the mansion, Dean uncovered the underbelly of a culture that – even if it afforded some women careers and sexual liberation – destroyed others. She heard women’s stories of being drugged, raped, and physically abused by Hefner and his associates; women committing suicide; women being used as drug mules; women being filmed without their consent; Hefner’s obsession with Charles Manson, his deep friendships with Bill Cosby, and Roman Polanksi. Behind the glamour of Anna Nicole Smith and The Girls Next Door, celebrity-filled parties, and Playboy casinos and clubs was a swampy network of coercion and abuse.

NYLON spoke with Alexandra Dean about how she hopes the documentary can change the legacy of one of America’s most influential brands, how to do justice to the stories of the women in Playboy, and how she built trust with her subjects.

Secrets of Playboy is on A&E on Monday nights at 9pm.

Why did you want to make this documentary?

I wanted to make this documentary because when I was in college, so many girls had the Playboy logo on their dorm wall or their tracksuit bottoms, and it felt like it was way of saying, “I’m sexual and playful and free,” and it felt like a really powerful American brand. When Hef died, I really did wonder if it was true that this brand had been so instrumental in making women feel that way: powerful, liberated, and free. I really wanted to take a closer look at it because I knew Hef had been really close with Cosby and there were some unanswered questions I felt around Playboy after that came out; a lot of the Cosby allegations had taken place at the Playboy mansion. I just wanted to see: Is it time for Playboy to have a reckoning?

This magazine and larger brand spanned decades and the depth of the interviews in this film are astounding. Where do you start with a topic as big as Playboy?

I was sitting in my little room and the pandemic had just hit. I was in this attic in Long Island with my children trying to figure out how I was going to work and what the world was going to look like. So making these phone calls became my communication line to the outside world. I began to forge these early kind of intimate relationships with all these women who had been in Playboy for decades and these phone calls were fascinating and uncovered so much, and the really crazy part was no two women I talked to had the same experience. Creating a picture using all these tiny jigsaw pieces was difficult. It was difficult to figure out how all these stories fit together when they were so different.

And they span so many eras, too.

They span so many eras. I wanted to create an overall picture of this brand that shaped us as Americans and made promises to us and some of those promises I felt had been broken.

It’s first and foremost a documentary about the stories of the women impacted by this culture. Is that the story you set out to tell or did the story change based on the interview and the depth of what you were hearing?

What happened when I started talking to these women at Playboy is I started to realize there was this vast world I didn’t understand, from the bunnies who had been these super famous iconic figures in American culture for decades, to the Playmates who obviously were still famous when I was a kid, to the girlfriends who had a moment in the 2000s, and all these women in the Playboy universe had they were in this kind of crazy hierarchy pyramid that had been constructed and that structure began to be what fascinated me.

Were you surprised that the women were so forthcoming with their very personal stories of abuse?

That took a long time. That was not immediate. At the beginning, I thought I was doing a different sort of show. I was trying to unlock this Playboy world for you and take you through the richness of it,there was a lot more looking at the culture of it. Overtime, as I began to form these relationships with the women, they began confessing things to me that really shocked me and it began to shift the story of what Playboy had really been.

“I wanted to create an overall picture of this brand that shaped us as Americans and made promises to us and some of those promises I felt had been broken.”

How did you work to build that trust and how did you take care of both the subjects and yourself in the process? Some of this stuff is so horrific.

What a good question. We offered our subjects access to therapy. I probably should have done a bit more therapy myself. My poor husband is probably the one that has done it for me. I think this kind of trauma requires really, really good therapy and if I had unlimited dollars, I think I would gift it to all of these women in perpetuity if I could. So many people I find When I do these docs, I find that so many people need more therapy and support. I wish we were in a culture where it was more readily available for everybody.

Totally. It did seem like for a lot of these women being able to share their stories, even if that was hard. It felt like a couple of them said this could help someone else, and there’s power in that.

Yeah, one of them texted me this morning and she said that the respect that the journalists she talked to in seeing the doc, the respect they showed her changed her world. She felt, for the first time, heard and she said she felt like Hef couldn’t hurt her anymore. That’s honestly why I do this stuff.

Do you think this documentary could only be made after Hefner’s death?

Absolutely. This could only be made after Hefner was dead because Hefner was so incredibly powerful. He not only controlled his vertical, the Playboy empire, for so long, but he also had a huge amount of control over the press in general. He had relationships with so many publishers. You can see in our episode how many people tried to write tell-all books about him and were squashed by his power, so I have no doubt he would have tried to squash this.

And do you think part of the reason why so many women were comfortable telling their stories was because he was dead?

100%. I think they were not only scared of telling their stories because of what Hef might do or how he might retaliate, but they were really scared of the other women because there’s a lot of women who will die on the cross for Hef and a lot of loyalty and that has to do with his complicated legacy. There are women he really did liberate and empower and they will fight hard for him, and they will often fight against women who said he wasn’t empowering for them or he hurt them. More often than not, I found that women were scared to speak because they were afraid of what other women might do to them.

In finding subjects, is that something you came across often? Women who were staunchly defensive of Hef?

Oh yeah, frequently. A lot of women really defend Hef and I don’t want to say their experience is untrue because I actually believe it's true. I believe a lot of women had a positive experience at Playboy and those women I think should celebrate their own experience. This doc shouldn’t take away from what it did for them. And I think those women who feel really really damaged and traumatized by Playboy should also be able to speak.

What was the most difficult thing about making this documentary?

The most difficult thing about making this documentary was trying to do justice to the stories I was being told. I felt such a burden of responsibility to tell these stories correctly, because I knew the risk each of the women felt like they were taking in telling me. I still feel that. I'm always so mindful of that and it’s a huge thing to carry, actually.

Absolutely. Is part of you nervous for what’s going to happen after it’s out or how they will feel after it’s out?

I actually can’t think about it because it’s too much. I have to distract myself with thoughts of my dog. I go and get a coffee. I can’t think about it; it’s too much.

What do you hope that people will take away? Do you think this doc could change the legacy of Playboy as we know it now?

I hope this documentary changes the legacy of Playboy. I think it’s time for this reckoning. I think Playboy has to be reevaluated. And you know what I really hope? That there’s a generation that sees this and feels like they can find another way to sexual freedom where they hold the reins of power for themselves and nobody else is debating what that looks like for them.

Right. There’s a way to sexual freedom where there’s also control and agency.

Yeah, and then we can celebrate that wholeheartedly, with no one being damaged by it.

What is the biggest misconception about Playboy that this documentary might change?

The biggest misconception about Playboy is that it was just fun and harmless. It wasn’t just harmless fun for everybody and it had an enormous impact on our country and the way we treat women. I hope everyone stops to think about that for a second.

“They like to celebrate Playboy together; that is often a source of strength for them, but they aren’t all telling each other what really happened to them. It broke my heart a bit. The secrets were really heavy at Playboy.”

I’m wondering how you initially approach someone with a doc that’s as intense and potentially emotionally difficult for them. What does that initial reach out look like?

The initial reach out was I wanted to hear about Playboy from the women’s perspective and I was really welcoming whatever story they wanted to tell me, whatever their real experience was. And I definitely listened to over 100 women.

On a procedural level, how did you begin to track down all the former Playmates? There’s an astounding number of interviews in this doc.

Luckily, there are published names; you know who was in each edition of Playboy, so for the Playmates it was easy, but for the bunnies and the people who worked at Playboy and some of the former girlfriends were a little harder. It was really a case of every time you gained someone’s trust, they would offer a few more people for me to talk to.

Did you kind of feel like once you were able to build trust it was easier to open the gates to others?

Yeah definitely, that’s how it worked. It was like a network or a web and it was sometimes funny to see that friends in friend groups would sometimes feel differently about Playboy and not necessarily know how differently they felt. They like to celebrate Playboy together; that is often a source of strength for them, but they aren’t all telling each other what really happened to them. It broke my heart a bit. The secrets were really heavy at Playboy. I hope that some women watch this and they feel like it means they can also share their stories because I know there’s a lot more that happened at Playboy than even I uncovered and I hope women start to have real conversations with each other about it, and I hope that it changes things for them.