Lovett or Leave It Presents: Bravo, America! (with Holly Madison)

Summary

Lovett or Leave It Presents: Bravo, America!

Episode Title: Finale with Holly Madison
Date: December 16, 2025
Host: Jon Lovett (Crooked Media)
Guests: Holly Madison, Lee Eisenberg (co-host)

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Episode Overview

The season finale of “Lovett or Leave It Presents: Bravo, America!” features a candid, in-depth conversation between Jon Lovett, Lee Eisenberg, and special guest Holly Madison. Madison, famed for her role on E!’s The Girls Next Door and her years as a Playboy Mansion insider, discusses her experiences inside the Mansion, the dark reality behind its glamorous façade, her journey to reclaim her truth post-Playboy, and the evolving cultural understanding of sexual exploitation, agency, and trauma.

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Key Discussion Points and Insights

1. Life in the Playboy Mansion and the Origins of "The Girls Next Door"

[03:04–13:45]

• Holly’s Mindset Pre-Show:

  • Holly describes herself as “a zombie” before filming began, citing the isolating, competitive, and demoralizing Playboy environment.
    • “It was just kind of this miserable experience... mean girl drama and being pitted against each other and feeling like you’re being judged by the outside world for the choice you made to be there.” (Holly Madison, 03:23)
  • She describes having to hide side projects: “We weren’t allowed to do that, so you kind of had to keep it a secret.” (03:53)
  • The show came as a decree from Hugh Hefner; participation was not voluntary for the women. (04:40)

• Lack of Agency and Contracts:

  • The women weren’t under any contract for the first four seasons. Representation and legal rights were heavily restricted.
    • “We went, like, four seasons, no contract.” (Holly Madison, 06:19)
    • She and fellow star Bridget were pressured, even harassed (e.g., being yanked from a shower), to eventually sign. (08:22)
  • All residuals and spin-offs were controlled by Playboy/Hef, with the women seeing none of the streaming or future profits.
    • “Nothing. Even when I tried to react to the show on YouTube, it got flagged—Playboy takes the money.” (Holly Madison, 10:18)

• Cultural Reflections:

  • Holly expresses fears of being “humiliated in the edit,” concerned the show would reduce her to a caricature or highlight shameful moments. (12:18)
  • Despite her initial resistance, she notes some positive outcomes: increased personal freedom, recognition, and small career opportunities. (13:43)

2. Toxic Dynamics and the Myth of Playboy

[13:45–23:26]

• Isolation and Competition Among Women:

  • Hefner sowed division among the women, pitting them against each other.
    • “Everybody wanted...the next Playmate pictorial...there was a lot of him pitting the girls against each other, which I was really blind to.” (Holly Madison, 18:17)
  • Holly admits her youthful inability to recognize multiple truths simultaneously—a binary that preyed on insecurities among the women.

• Disillusionment with the Playboy Fantasy:

  • Playboy’s image was carefully manufactured in documentaries and television:
    • “It just makes his lifestyle in the Playboy world look so amazing...Like anybody would want to be a part of it.” (Holly Madison, 20:47)
  • Holly clung to the ideal even after harsh reality set in, feeling a “sunk cost fallacy.”

• Objectification and the Reality Show Perspective:

  • The show reframed the women's narrative, unexpectedly creating a female fanbase.
    • “I think...it was playful, you got to see us having fun...it was this...bright, fun look into a lifestyle...before social media, this was novel.” (Holly Madison, 25:50)

3. Inside the Relationship with Hefner

[27:59–35:15]

• Attachment and Manipulation:

  • Holly acknowledges an early connection with Hefner, which was ultimately rooted in manipulation and control.
    • “He’s very big on, like, love bombing. And I was 22 and hadn’t really had many relationships...and I kind of, like, fell for it.” (Holly Madison, 28:28)
  • Hefner used relationships as self-validation, repeatedly chasing women who tried to leave, reflecting his aversion to change and desire for control.
    • “He didn’t want things ending on someone else’s terms...that kind of activates him to chase more.” (Holly Madison, 34:04)

• Departure from the Mansion:

  • Holly’s exit was catalyzed by disappointment (IVF failing), realization of never becoming a mother with Hefner, and a breaking point after Hef sent security to follow her in Vegas.
    • “I always knew I wanted to be a mom...I was already wanting out anyway, so I left.” (Holly Madison, 33:10)

4. Aftermath, Public Perception, and #MeToo

[37:15–44:25]

• Reconciling Trauma and Coming Forward:

  • Right after leaving, Holly wanted to treat her Mansion period as a “curiosity piece” and only later processed the depth of her pain.
    • “I was like, holy shit. I’m fake smiling in all of these and I’m so miserable.” (Holly Madison, 38:13)
  • Writing her book was both cathartic and controversial; early reactions were largely unsupportive—“Back in 2015, MeToo wasn’t mainstream...People didn't have a thought as to why a casting couch could be problematic. People were just like, fuck you, bitch, you wanted to be there...Now I think people understand better.” (39:49/40:01)

• Hefner’s Death and the Culture Shift:

  • Holly refused to make a public mourning statement.
    • “I think it’s kind of gross that people are expected to mourn publicly. I was disconnected from him.” (41:23)
  • Hugh Hefner’s passing was followed almost instantly by the Weinstein revelations and the MeToo movement.
    • Holly expresses relief: “I was just so glad that women were finally able to be listened to and have a voice.” (42:42)

5. Lingering Power Imbalances, The Legacy of Playboy, and Women’s Sexual Agency

[44:25–46:52]

• Ongoing Societal Blindness:
  • Holly reflects on the dangers of aesthetics and nostalgia erasing harmful truth:
    • “I do worry about just people being fascinated with the aesthetic and ...I just hope that it doesn’t get glossed over again.” (Holly Madison, 44:25)
  • Discussion delves into unresolved gendered double standards around sexual liberation, with Holly highlighting the emotional impact of sex, particularly for women.

6. Redemption, Moving Forward, and Retrospective Wisdom

[49:34–61:49]

• Post-MeToo Reception:

  • Holly observes a welcome shift:
    • “For the past, you know, six or seven years, people have been so much more open to hearing my story and understanding and I feel seen and heard.” (Holly Madison, 49:45)

• Reflections and Regret:

  • When asked if she misses Mansion life, she only reminisces about innocent bonding with fellow women—never the world Hef built.

• Beauty, Fame, and Neurodivergence:

  • Holly addresses her early pursuit of external validation, linking it to her undiagnosed autism, a desire for connection, and her fascination with old Hollywood icons.
    • “Fame does not make you feel loved in any way. But as a kid, I think I thought that, and I think that’s kind of what pushed me in that direction.” (Holly Madison, 53:05)

• Current and Future Ambitions:

  • Holly works in true crime TV, loves Las Vegas, and jokes about potentially running for mayor.
  • Passionate advocacy: protecting women’s rights to privacy—especially old Mansion photos Hefner hoped to donate to a public archive, many of which are explicit and non-consensual.

• Final Advice:

  • “Lean into yourself and don’t be afraid of what other people are going to think... Don’t make fear-based decisions. It’s never too late to step out or find something new.” (Holly Madison, 60:51)

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Notable Quotes and Memorable Moments

• On Being Forced into Reality TV:
  • “I hoped the TV show could be a good opportunity, but...I kind of didn’t really want to be there and kind of felt like I had to do it unless I wanted to leave that day and start all over...” (Holly Madison, 05:20)
• On Exploitation and Lack of Compensation:
  • “They didn’t blur my vagina.” (Holly Madison, 11:20, wryly noting the extent of the exploitation)
• On Post-MeToo Recognition:
  • “For the past...years, people have been so much more open to hearing my story and understanding and I feel seen and heard.” (Holly Madison, 49:45)
• On Leaving Toxic Relationships:
  • “Lean into yourself and don’t be afraid of what other people are going to think...It’s never too late to step out or find something new for yourself.” (Holly Madison, 60:51)
• On Hefner’s Legacy:
  • “Even when I look back at...good qualities and nice moments, to me it seems very artificial.” (Holly Madison, 59:51)
• On Regret and Growth:
  • “I would just encourage people to not make fear-based decisions.” (Holly Madison, 61:05)

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Timestamps for Major Segments

• 03:04 – Holly’s state of mind before Girls Next Door
• 06:19 – No contracts, no pay, and manipulation by Playboy/E!
• 13:45 – Effects of the show, shifting dynamics in the Mansion
• 18:17 – Competition and infighting among the girlfriends
• 20:47 – The myth vs. reality of Playboy through media
• 25:50 – Why “The Girls Next Door” resonated with women
• 28:28 – Nature of Holly and Hef’s relationship
• 33:10 – Deciding to leave the Mansion and breaking point
• 38:13 – The moment Holly reevaluates her whole experience
• 39:49 – Writing her book and early backlash
• 41:23 – Refusing public mourning after Hefner’s death
• 46:50 – The emotional impact of sex, gender, and cultural narratives
• 49:45 – Being “seen and heard” after #MeToo
• 60:51 – Final advice for listeners

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Podcast Tone and Language

True to Lovett or Leave It’s signature blend of incisive political/cultural commentary and humor, this episode features equal parts compassion, critique, and wit. Holly is candid and precise, discussing deeply personal and often dark subjects with self-awareness, empathy, and honesty. Lovett and Eisenberg balance sensitive questioning with respectful levity, allowing both the gravity of Holly’s testimony and the absurdity of the Playboy myth to sit side by side.

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For fans of pop culture, politics, or anyone interested in the intersection of media, power, gender, and trauma, this episode offers a revealing, necessary conversation about the cost of fame, the complexity of consent, and the ongoing struggle for women’s autonomy and truth.

Transcript

[Jon Lovett]

This podcast is supported by the Obama Foundation. This holiday season, emerging leaders are stepping up to tackle the toughest challenges of our time, from strengthening democracy to building more just communities. But they can't do it alone. The Obama foundation believes leadership isn't about one person. It's about equipping the next generation of change makers with the tools, skills and community to turn ideas into action and hope into lasting impact. Through programs, mentorship, and community engagement, the foundation equips young leaders with the skills and tools they need to tackle today's toughest challenges, from civic engagement to education, education, social justice, and climate action. Your gift makes this important work possible. Join the thousands of supporters who have already invested in the future of leadership. Donate today by visiting obama.org youth that's.

[Lee Eisenberg]

Obama.Org youth you had a, I think a pretty good case to sue for a lot of money for the ways in which you were not compensated for being on a television show. Like they would they didn't blur your face. You didn't approve your likeness.

[Holly Madison]

Being youth, you didn't blur my vagina.

[Lee Eisenberg]

Right? So which is the face of the lower half of the body?

[Holly Madison]

Yeah.

[Jon Lovett]

Love it or leave it.

[Holly Madison]

It's Love it or leave it.

[Jon Lovett]

Hey, everybody, it's Jon Lovett. And welcome back to Love it or Leave it presents Bravo America. This is the finale to our first season where I have sat down with some of my favorite reality stars because you cannot understand politics in this moment.

[Lee Eisenberg]

If you don't understand the dynamics of reality television. These have been an amazing series of conversations with Bravo stars and Survivor winners and escapees from right wing religious communities and more.

[Jon Lovett]

I've loved getting to do it and I've loved how much there is to learn about politics and culture in this.

[Lee Eisenberg]

Moment from people who have been in.

[Jon Lovett]

A world where the only thing worse than being hated is being boring.

[Lee Eisenberg]

Today I'm joined by Holly Madison from the E. Channel's the Girls Next Door. She was one of Hugh Hefner's girlfriends at a time in which the Playboy Mansion was a cultural phenomenon and the glorification of the Playboy lifestyle took over tv. Holly is so smart and thoughtful. In this conversation, we talk about what led her to the Playboy Mansion, rising to the top in the Mansion, and how she was often villainized, but both for being part of that world and then for walking away from it.

[Jon Lovett]

We also talked about how since MeToo.

[Lee Eisenberg]

She'S found a much warmer reception from a lot of people, including a lot of young women. It was a great conversation not only about where she's been, but also what she's learned, advice she has for young people, and what her future might be up to and including being a candidate for elective.

[Jon Lovett]

So be sure to catch her rewatch podcast, Girls Next Level with Bridget Marquardt, as well as the Playboy Murders and.

[Lee Eisenberg]

Lethally Blonde, which she hosts on I D. So I hope you enjoy it.

[Jon Lovett]

Here's Holly Madison. Holly Madison, welcome.

[Holly Madison]

Thank you.

[Lee Eisenberg]

So I want to get into the Girls Next Door, but I do think it's helpful, before we do, to understand what your mindset is. Before the filming of that show began, you've lived in in the Playboy Mansion for several years. At this point, you've described yourself as a zombie. When the taping began. Why were you a zombie?

[Holly Madison]

Oh, that situation we lived in. I feel like, where do I start? Yeah, that situation we lived in was so crazy. When I started doing a rewatch podcast with my co star, Bridget, we did a whole. Before we even got into the first episode, we probably did, like, six episodes that I called the prequel episodes, where we were just explaining, like, what happened up until that point. So we were all living at the Playboy Mansion with Hugh Hefner as his girlfriends. And it was, for me, I can't speak for the other girls, but for me, it was something I felt like I thought was, like, a good idea at the time, but I got in way over my head. And it was just kind of this miserable experience where it was a lot of, like, mean girl drama and being pitted against each other and feeling like you're being judged by the outside world for the choice you made to be there. So you're not super eager to leave yet, but you kind of want to. So there's a lot going on. And I was trying to kind of audition on the side for other things during the day. You know, we weren't allowed to do that, so you kind of had to keep it a secret. But I was trying to save money, get, you know, I was going to real estate school, do all the things, trying to get something else going on. And then this idea for the reality show came about, and we didn't have a choice. Like, do you want to do this? It wasn't like we all sat around and made this collective decision, like, do the three of you girls want to do this show with me? It was like, I'm doing this show. And I was like, holy shit. I felt scared. Like, I'd always wanted to experience that feeling of, like, being famous or being in the public eye, but I always wanted to do it, like, As a TV host or something like that, or in a role I didn't want to, you know, be famous for my personal life, especially being in this relationship that I was confused about. I had a lot of issues with. There was a lot of shame involved in it. So, you know, dealing with the depression of being there for four years and everything, I was kind of like a zombie. I was also on the spectrum undiagnosed. So I don't really emote the way a lot of people do, and sometimes I can zone out and look very dead behind the eyes. So I watch myself in season one, and I'm seeing all those layers, and I'm like, I am a zombie. But I also knew that I hoped the TV show could be a good opportunity, but, like, I kind of didn't really want to be there and kind of felt like I had to do it unless I wanted to leave that day and start all over with, you know, what I felt was nothing and. Yeah.

[Lee Eisenberg]

So did you have an agent at this time? Because there are periods of time where you had an agent. Did you have one at this moment when. When E is showing up to do this show or. No.

[Holly Madison]

In college, I did, but when I moved into the Playboy Mansion, I no longer had an agent, and we weren't allowed to work or anything like that. So I would have, like, kind of a modeling agent on the sly and maybe go on a few auditions and things like that. And then, you know, once the show started, we were expected to be represented just by Playboy, so we didn't have any of our own representation. Even when contracts came up, we weren't allowed to have, like, our own attorney. Look at the contracts. We just were expected to sign right then and there. Like my costar. It was weird. We didn't even sign contracts until right before. So we went, like, four seasons, no contract.

[Lee Eisenberg]

But that's what I was gonna. No, you're saying you're in a reality show. You are being filmed in a private home day after day after day, and you have signed nothing?

[Holly Madison]

No contracts, Nothing? Yeah.

[Lee Eisenberg]

Had you signed anything to be in the mansion? Like, had you signed something? So you, as far, you have not signed a document?

[Holly Madison]

No.

[Lee Eisenberg]

As far as, you know from the. You come to the house, and then you decide to live in the house. You are receiving $1,000 a week. You are required to be there at certain times and do certain events. Then you are on a reality show, and you've never signed anything?

[Holly Madison]

No, nothing. Not until right before season five.

[Jon Lovett]

Wow.

[Lee Eisenberg]

That's shocking.

[Holly Madison]

Absolutely. It really Is. It's weird. And it was really strange. It's funny. We were just on my podcast, Bridget and I were talking about the first episode of season five, rewatching that. So we were just talking about this contract thing. And it was very weird the way it happened because there were three of us on the show, me and Bridget and Kendra. Kendra was doing a club appearance in the Dominican Republic, so she wasn't there the day this happened. Bridget and I were at home. I think I was working at the Playboy studio at the time. So, like, I was at work, she was at home in the shower. And that day, all of a sudden, at least the way it was presented to us, I feel like this is a little fishy and weird and probably not really the way it went down. But according to Playboy, E suddenly realized that we weren't under any kind of contract and freaked out and said, no more show, which we're four seasons in at this point. Even I, who'd been the most reluctant to do the show, like, I'd started to realize, well, this is how the show can work for me, and these are the benefits, right? So all three of us were very invested in the show and wanted it to keep going. And we were told one day, it's like, no more show unless you sign this today. And I was hesitant. And I was telling Hef. I'm like, well, this is weird. Cause, like, we're living here as your girlfriends. I don't know if I want to sign a contract. That in essence means I'm signing a contract to be a girlfriend. That's weird. Granted. I mean, there was a lot of other weird shit that led up to that. I don't know why that was the one thing I finally felt like, oh, this is really, you know, pushing the limits here.

[Lee Eisenberg]

I wish you had, like, one lawyer friend in this time. My God, I know.

[Holly Madison]

It was crazy. And Bridget was the one who said, you know, she had said, I think, to have secretary who had been the one who called us initially and told us we all needed to sign. She said, well, I wanna have, like, an attorney look at this. And, you know, she's going about her day. She's in the shower, and Hef comes into her room, is yelling at her, opens the shower, literally yanks her out of the shower and says, you need to sign this fucking shit right now. He said, you're the last else has signed. Which I don't even know if that was really true at the time. She's like, sobbing, saying she doesn't want to Sign it. She wants somebody to look at it. And he's just told, you're the only one. Everybody else wants to do this. You're the only one holding this up. You need to sign it now. And she's like, okay, like, let me get dried off.

[Lee Eisenberg]

Ah.

[Holly Madison]

I know. It was weird.

[Lee Eisenberg]

Do you know if that contract was retroactive to the previous seasons or was it just for season six?

[Holly Madison]

It was for seasons five and six.

[Lee Eisenberg]

Five and six.

[Holly Madison]

So they ordered, like, a five and six. But also the contract with E Determined how we were gonna do our spinoffs if we did spinoff. So when I eventually moved out on my own and then did a spinoff with E, which I was super excited to do, I had to do it under the same production company that had done Girls Next Door, meaning somebody who's very close friends with Hef. He had to get a cut of it. You know, he had a credit on it. So even when you're out there, like, on your own, like, they're still taking a cut. So it was a. It was a contract that had, you know, lasting effects down the line.

[Jon Lovett]

Did you ever have.

[Lee Eisenberg]

I'm sorry to dive into this, but I actually. I thought. I assume the answer was you signed a shitty contract all the way through. I'm actually genuinely stunned to find out that nothing was signed along the way. Did you ever talk once you got out, and we'll get to getting out, but did you ever talk to an entertainment lawyer about what your options were, your rights were for? I mean, right now you can go and stream seasons. Yeah, all the seasons of the Girls Next Door. Presumably somebody's making money when people click play on this. I was on Amazon Prime. You don't get anything from the show.

[Holly Madison]

Nothing.

[Lee Eisenberg]

Nothing.

[Holly Madison]

Even if I. When I first. Before I did the Rewatch podcast, I had a YouTube channel, and people were saying, we'd love to have you react to these old episodes. And I tried to do a reaction video where you could kind of see the show on. On the video where I'm talking about it, like tons of people do on YouTube. It's fair use. And I know fair use is a slippery slope, but I put that on there, and it immediately. Like, I had uploaded it, but before it had even popped up on the channel. Like, Playboy has the software in there that, like, scans everything on YouTube, which is weird to me, because I don't even think they own the show. I think it's Fox owns the show. But Playboy had this software that scans everything. So I immediately got an alert that my Video was flagged and they were going to get the money from it. So I took the video down. I was like, fuck that.

[Lee Eisenberg]

I'm going to move off of this. But I'm generally gobsmacked. But did you ever have a conversation with an entertainment lawyer once you were out of the Mansion about what your rights were? That you had a. I think a pretty good case to sue for a lot of money for the ways in which you were not compensated for being on a television show? Like they would. They didn't blur your face. You didn't approve your likeness being. You know.

[Holly Madison]

They didn't blur my vagina.

[Lee Eisenberg]

Right. So. So which is the face of the lower half of the body.

[Holly Madison]

Yeah.

[Lee Eisenberg]

So.

[Jon Lovett]

But.

[Lee Eisenberg]

But. But did you. But. But did you ever talk to anybody about what your recourse was after you left? Did you think about that at all?

[Holly Madison]

No, I. I never thought about that. Like any. It's one of these things where anytime I speak, speak up about it. I'm kind of told by a lot of people, shut up. Just be grateful you got the exposure. So it honestly didn't even occur to me. Like, I know it's not fair, but didn't occur to me.

[Lee Eisenberg]

I wonder if there's. Is there anything we can do now?

[Holly Madison]

Maybe I should.

[Lee Eisenberg]

If you have a lawyer, if you're an entertainment lawyer, drop something in the comments. Can't be worse than the current situation of getting nothing from this show. Okay, so the girls next door, it's happening all around you all of a sudden. You have no say in it. What were you feeling when that happened? Were you excited about the fame of it? Were you nervous about people finding out what it was really like?

[Holly Madison]

I was really, really nervous. I knew they weren't gonna find out what it was really like, because I knew everything was kind of gonna be sugarcoated. And it was on E. So nothing was gonna be too explicit. So it wasn't really that. I think I was just worried about being judged. And when I made the decision to move into the Mansion, I always thought, oh, this is like the crazy thing I'm doing in college. And one day I'm gonna go out and make it. And then people are go find out about this after the fact. And it's gonna be this weird little, like, curiosity piece about my past. I never thought it would be, like, the thing I was known for. So I was nervous about that. Cause it wasn't really the direction I wanted to go, but I hoped it could be some kind of opportunity. I thought, well, you know, Maybe we can finally get that magazine pictorial we always wanted. Maybe I'll finally get noticed for something else. So, you know, I found maybe around the time of, like, season two, it actually had other benefits that I hadn't anticipated because living at the Mansion was weird. You're in this weird bubble. You have a 9pm curfew, you're not allowed to work all these things. But because we needed plot lines for the show, you know, that came up like, oh, well, maybe we could, like, go to Vail and learn how to snowboard, but we'll have to stay overnight. So that was so exciting to me because I'd been living at this house for four years and hadn't had, like, one night away. So I'm like, oh, my God, like, we can finally travel. And it's an excuse for me to, like, apprentice at the Playboy studio, which I always wanted to do, and that turned into a job there. So I thought, you know, this. This is good just for the opportunities.

[Lee Eisenberg]

So I was listening to you and Bridget talking about it, and I believe she described it as, in some ways, the best of times and worst of times in the Mansion, because on the one hand, there was all this tension and. And isolation that you felt, and not to mention the ways in which you are kind of have lost all your independence because of the way Hugh Hefner controlled your life, while on the other hand, the show protected you in some ways. Can you talk about that? Like, how did filming the show change what it was like to live in the house?

[Holly Madison]

Oh, a lot of ways. One way was we became famous, so we had more value to Hef. Like, I felt like all of a sudden, he was, like, so in love with me and wanted to settle down with me and was like, okay, if the other girls left eventually. He wasn't, like, so hung up on, like, having a million girlfriends. You know, we got to travel. We got to do other things. There wasn't, like, these, like, compulsory, like, going out to nightclubs and, oh, let's all go upstairs afterward, or, like, him trying to, like, pick up on other girls and things like that because he was so obsessed with the show and having so much fun with it and, like, the ego boost it brought to be, you know, relevant again. He wasn't really seeking the validation by, like, going out to nightclubs and trying to pick up on a million girls like, he was right before.

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[Lee Eisenberg]

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[Holly Madison]

You should do it.

[Jon Lovett]

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[Lee Eisenberg]

One thing you talk about is the ways in which you were pretty isolated from the other girlfriends and that some of them were pretty nasty. And I wonder if you've thought about what prevented you all from seeing each other as allies, that you were in this situation together, like, you were hating the players. But look at this game. Like, was this a kind of, I don't know, a psychological reaction to the fact that people didn't want to be there? Like, what explains to you why that instead of directing frustration at Hugh Hefner, you were fighting with each other or people were really kind of targeting you?

[Holly Madison]

I feel like part of it was competition between the girls. Like, everybody wanted, you know, the next Playmate pictorial in a magazine, or they wanted to be bought something special or something like that, or they were even competing for other things outside. Like, they wanted to, like, date certain celebrities. Who could we meet at the party? So there was a lot of competition between the girls for things like that. And there was a lot of him pitting the girls against each other, which I was really blind to from most of the years. And a lot of it was me blaming the other women, and there were some nasty people that went through there, but a lot of it was me just blaming the other women and thinking. Because back then, I just had such a binary way of thinking where I thought, like, if somebody is this, you know, accomplished and intelligent and, like, has the world at his feet, why would he be so petty as to, like, pit all these girls against each other? Like, it didn't compute to me. Like, I didn't realize two things can be true at once. You know what I mean?

[Lee Eisenberg]

Does it compute to you now?

[Holly Madison]

Yeah, 100%.

[Lee Eisenberg]

It is. Like, the reality of life in the Playboy Mansion is shocking in part. It is shocking because it was glamorized and celebrated and held up as this fantasy for a very long time. And then, even though obviously that's not gonna be true, the actual reality is so much worse than I think even cynical people would imagine. Like, how did you feel about the image of Playboy, and how did it change when you were there? Did it disappear immediately? Did you cling to it? Like, what did the fantasy become?

[Holly Madison]

You know, I think I clung to what I wanted it to be, and I thought I could change it into that because I felt so involved. Once I was there, I had kind of this sunk cost fallacy where I moved in and was kind of surprised at how immediately everybody in my circle and everybody I interacted with in the world kind of knew I was there and was so shocked by it and judgy all of a sudden, and I was like, wa. Nobody thought it was weird when I was just going to the parties. Like, everybody thought that was so cool. But, you know, it kind of, like, pushed me into myself a little bit more, I feel. And I felt very isolated because of that. But there had been, like, a couple of documentaries put out about Playboy at the time that I think are really good examples of this. There was one I recently rewatched for a podcast. It's called Inside the Playboy Mansion, and it aired on A and E back in, like, 2000, so right before I moved in. And if you go back and watch this thing, I. First of all, there's so much that doesn't age well in there, like Bill Cosby being interviewed as a talking head and stuff like that.

[Lee Eisenberg]

But that's rough.

[Holly Madison]

I know, but it just makes his lifestyle in the Playboy world look so amazing. Like, anybody would want to be a part of it. Oh, and, you know, if you're really lucky, you get to be one of his girlfriends that live in the house, and they make it just look like this cute little sorority thing where everybody's having fun together. So I fell for a lot of that, and then I moved in and not long after realized it wasn't like that at all. And. But I felt so involved, and I felt so branded by the whole thing, which, you know, I could have pulled myself out of that and told myself, that's not true. Just go out and do something else. But that's how I felt at the time. I thought, no, I need to, like, make this better. I need to make this what I thought it was going to be. And in a weird way, I feel like, you know, Bridget and I kind of banded together and did that. And when girls next door came along, we did get something positive out of it through that experience. But, yeah, it was a wild ride.

[Lee Eisenberg]

So it is clear that the Playboy fantasy was mostly a fantasy for men. But was being an object of desire exciting to decide even from a young age? I want to pursue being in Playboy. I want to go audition. You saw yourself as beautiful. You took a lot of pride in that. Like, what was the fantasy for you?

[Holly Madison]

Well, I think growing up, like, in the 90s, you saw, you know, a handful of, like, famous women who came from Playboy who started out being Playmates, and you would see the ads on TV for Playboy subscriptions, and it would show all the Playmate videos, and everybody looked so gorgeous. You Know, this was back before Instagram face and filters, and everybody knew how to do their makeup from a YouTube tutorial, so women just didn't look like that. And I wanted to look like that. I thought, oh, if they could just take a chance on me and make me look like that, you know, that could be my stepping stone, and life would be amazing. So I really wanted to be a part of it, and I just thought it looked, you know, like, so much fun. And going to the parties was really fun. And back then, that was, like, the cool guest list that you wanted to be on.

[Lee Eisenberg]

And so now you're part of this male fantasy. Then a show comes in that really is. You know, it's strange, the show, because on the one hand, it doesn't show a lot of, like, the sexual parts of what life in the house was about, but on the other, it's really about, like, you as people. Right. And in the fantasy, you're objects, but on the show, you're the leads. Like, how did Hugh Hefner feel about that, about the fact that there was now this show about the mansion in.

[Jon Lovett]

Which in a lot of episodes, he.

[Lee Eisenberg]

Kind of pops in, kind of wanders in, wanders out, and the pilot, like, you're at a party, and he's eating ice cream in his sort of hoarding.

[Jon Lovett]

Bedroom covered in things.

[Lee Eisenberg]

Like, it's not glamorous for him. At least that's in my viewing of it.

[Holly Madison]

I think from his perspective, you know, reality TV was, like, the cool new thing at the time. And this idea came up, and a couple different iterations were passed by him. Like, it started on A and E. They were doing a show called Growing Up Gotti about John Gotti's grandsons. So what they wanted to do was Growing Up Hefner because he was divorced, and next door, his wife and two kids lived. So they wanted, like, Hugh Hefner going to PTA meetings. And he's like, absolutely not. I'm not doing that. So then they tried to do a version that was kind of like Downton Abbey. Upstairs, Downstairs. It was about the staff.

[Lee Eisenberg]

Yeah, I saw that.

[Holly Madison]

Spoiled bitches they have to wait on.

[Jon Lovett]

Right.

[Lee Eisenberg]

The unaired pilot. And they're all kind of, like, dreading having to bring him the soup.

[Jon Lovett]

Yeah.

[Lee Eisenberg]

And it's like, oh, I drew the wrong. Literally, they draw cards to bring Hugh Hefner the soup. He must have hated that.

[Holly Madison]

Yeah. But eventually, the people at east saw the pilot, and they saw, you know, the three of us girls had been interviewed, and she, the lady at East Said, I want to see this world through the girl's eyes. I want it to be like Alice in Wonderland. So that's what ended up happening. And I think by the time that happened, Hef felt invested enough in the idea of having a reality show about himself, and, you know, he felt he had enough control over us that we weren't really going anywhere. And when we would go out and do press about it, he'd always kind of joke like, daddy doesn't have to do the work. Which gag. But that was his thought. It's like, I get to have this cool TV show about my world, but they're doing all the work. And then as the show became more and more popular, he wanted to be a part of it more. So they would stick little scenes in there, like, if the three of us would be, like, out of the country for my sister's wedding, they would do these scenes back at the mansion that really had no point, but just a reminder that, like, Hef's still there and he wants to be in the show, kind of.

[Lee Eisenberg]

So the show then becomes a hit among young women. Like, young women are really watching this. So you're opening the doors to this, like, icon of old school male fantasy. And then the people that are watching it are girls. And why do you think that is?

[Jon Lovett]

What.

[Lee Eisenberg]

What do you think made the show so exciting or appealing to women?

[Holly Madison]

Well, I think that was a surprise to everybody because at the time we came along on E, they were mostly showing just, like, videos of the Howard Stern show. So I think they thought this would be like, a show for men, but women really attached to it. I think just because it was playful, you got to see us having fun all day. And it was this really, like, oversaturated, bright, fun look into a lifestyle which today you can see anybody's lifestyle on Instagram. But back before social media, this was really, really novel.

[Lee Eisenberg]

Yeah, I was thinking about this too, and the fantasy really falls apart. The idea of this sort of glamorous mansion disappears the second you actually see people living it. And Hugh Hefner kind of stumbling out of his bedroom in a robe for his girlfriends because he's an old man and they're young women, and he doesn't belong there, and it doesn't seem like he wants to be there, or at least he wants to want to be there. And I wonder what it was like for you to watch the show as it was airing and see what this looked like from the eyes of the young women who were watching it.

[Holly Madison]

I never really watched it. Through those eyes. I watched it through the eyes of, like, oh, my God, I hope they don't completely humiliate me in the edit, you know? Cause in season one, I didn't know what to expect. Like this. I always use this as an example. Like, back then, what was, like, fresh in my mind was there was a season of the Surreal Life where, like, Verne Troyer, who played Mini Me and Austin Powers, got super wasted, got naked, started rolling around on a scooter, got caught masturbating in bed on camera. And I'm like, this is what they want. So I was, like, so scared of, like, stuff like that. Or I was scared of, like, a really crazy bad edit. And they did a few edits I didn't really care for, like, trying to make me look jealous of people I wasn't jealous of and things like that. But when it turned out it wasn't that, and I started to see the show as, like, this cute thing that's getting a fan base and seems to make people happy, and it's kind of giving us these kind of other opportunities and the ability to do things that we weren't allowed to do before. I started to embrace it more, but that didn't happen until, like, season three was when I really started to get into it.

[Lee Eisenberg]

So the relationship between you and Hef, as portrayed on the show, is at times infantilizing, but there was, like, a genuine connection, or at least the portrayal of a genuine connection. Your love of old Hollywood and classic.

[Jon Lovett]

Films.

[Lee Eisenberg]

Was that reflective of life off camera? Was there genuine connection between the two of you where the rest of the kind of life there disappeared?

[Holly Madison]

Yeah, and I think that was one of the problems with me is very early on, you know, he and I kind of attached. You know, we like to do some of the same things. I was always very fascinated with him as, like, a businessman and a creative and everything he'd accomplished. And later on, we'd end up working together when I was directing the Playmate pictorials and things like that. So we bonded pretty early. And he's the type of person that likes to, you know, have a very romantic relationship with one girl, but also have all these other girls on the side. And he's very big on, like, love bombing. And I was 22 and hadn't really had many relationships up until then and kind of, like, fell for it, like, hook, line and sinker, and thought it was just gonna be us. And, like, well, why haven't you got rid of the other girls yet? You keep talking about it. You Know what I mean? Meanwhile, the other girls are like, who's this fucking bitch who's trying to get us kicked out? But they don't know about the conversations we're having behind the scenes? So it was a mess. But I mean, there was connection in a way.

[Lee Eisenberg]

In a way?

[Holly Madison]

Yeah.

[Lee Eisenberg]

But why? What do you mean in a way?

[Holly Madison]

Because I think he's manipulative. I think if he thinks of a girl as smart, she's just smart for a girl. I think he always wants to have the control, you know. And I think of, you know, he would always describe himself as a romantic. And I think in a way he believed that. But I think his idea of romance is more like playing house. It's more like, you know, talking the talk, but not actually, you know, investing in anyone or being monogamous or anything like that.

[Lee Eisenberg]

Did he ever talk about politics? Do you ever talk about. Did he vote for Obama in 2008? Did it ever come up?

[Holly Madison]

Yeah, I mean, he was always very Democratic, so I always knew where he stood 100%. He didn't love to talk about politics with his friends. His friends were mostly conservative and I heard. And nobody really talked about politics there because their interest, you know, they were interested in other things. Like he would have a night where his friends would come over and they talk about old film. And then he would have like a card night where they play poker or whatever. But I heard after I left that the. Of course. Cause I left, you know, before like 2016. But I heard after I left, like the social life just got crazy. Like people arguing about politics, like the second he went upstairs, like people screaming in the dining room.

[Lee Eisenberg]

Like even like the girlfriends.

[Holly Madison]

No, just like his older friends and things like that.

[Lee Eisenberg]

Wow. Even 2016, even the Playboy Mansion was not immune from 2016. You know, you said that like he would refer to himself and others would refer to him as Daddy. There's a pretty horrifying moment when a woman you refer to as the recruiter invites daddy to the bed with Bridget. It's really kind of hard to listen to. Did he think of you as daughters? Did he treat you like daughters that he also wanted to have sex with? Like it. There's something. There's something uncomfortable about the way in which he kind of was a parental figure.

[Holly Madison]

Yeah, definitely not like daughters. I just think it was super controlling and just super like stereotypical creepy old man who's old and wants to date a 20 year old. I think with a dot. I mean, he actually had a daughter and I think with a Daughter. He thinks of that as an extension of himself. And we didn't have any of that egotistical investment.

[Lee Eisenberg]

Right. So you live at the playboy mansion from 2001 through the first few seasons of shooting the Girls Next Door. Was that like, seven?

[Holly Madison]

I left in 2008.

[Lee Eisenberg]

So seven years.

[Holly Madison]

Yeah.

[Lee Eisenberg]

What was the moment where you're like, all right, I'm good. I'm out. I'm finally ready to leave? Like, what was there a singular event? Was it? What happened?

[Holly Madison]

Well, as the show went on, the relationship between Hef and the other girls just got completely platonic. And, you know, we were presented on the show all as girlfriends, but it wasn't really operating that way. And Hef and I, you know, like I said before, like, the second I got famous, then I was okay to settle down with, you know, he'd been love bombing and talking the whole time. But it wasn't until I became famous and the fans of the show really thought our relationship was cute and liked our relationship that he was like, oh, yeah, maybe this is my next step. Cause he loved to reinvent himself. He was a creature of habit. But if you look at his life, every 10 years or so, he'll, like, reinvent himself and do another thing. So we were actually doing in vitro, and then that didn't work out. I was told his sperm was too old, never going to happen. And I was like, I don't know if I can stay here. Like, I always knew I wanted to be a mom, and that wasn't something I wanted to give up. But I was so emotionally invested in him and that world. And so it was hard for me. I was kind of, you know, struggling with a lot of depression around that time and didn't really know what I was going to do. And I was in Vegas one night and went out with a guy. Nothing happened. It was just a guy I thought was cute. But I'm like, I feel. I'm so confused. I feel like I need to go out. And then if I miss Hef and want to go back, then I know. And if I don't, then I know. And unbeknownst to me, he had security following me that night. I'd only been in Vegas. Cause I was doing a shoot, a Playmate shoot. So I was there to stay one night, but he had security follow me. And he called me and said I gave him the worst night of his life. And I'm like, oh, I can't do this anymore. And then he was begging me to stay. And I'm like, Absolutely not. Like, I knew he was gonna hold this over my head for the rest of my life, and I was already wanting out anyway, so I left.

[Lee Eisenberg]

Why did he care? Why did he want, like, he clearly has, like, such a narcissistic worldview. He has objectified you in a long list of other women. Why would he care if you wanted to leave? He had another woman in the house already that he could elevate to promote.

[Jon Lovett]

To the number one spot. Like.

[Lee Eisenberg]

Like, what do you think it was? Other than your incredible qualities? I wanna start by saying that. I'm not saying you don't have. You're a special and wonderful person, but it doesn't seem like he saw you as a full fledged human being. So what was in it for him?

[Holly Madison]

I think one thing is he didn't like, change. And it's a pattern I've noticed with him over the years. Even, you know, he used to tell a story about how when he got married in the 50s, you know, he'd been seeing this woman and he'd been in the military, and he came back and she confessed that she had cheated on him, but that made him want to marry her more because he had to win. And then, you know, he went on to start Playboy, they got divorced, blah, blah, blah. We all know what happened after that. But even throughout the years, like, if you look at, you know, the story of, like, him dating Barbie Benton or, you know, the woman he dated right before me, like, when they wanted to leave, he would always chase after them because I think he didn't want things ending on someone else's terms. You know, he was a creature of habit. If he felt comfortable with somebody and they one day, you know, out of the blue, in his mind, say, they want to leave, you know, he doesn't want that. And that kind of activates him to chase more. But it would usually get to that point when the woman was, like, completely done. I mean, even after me, he was dating a woman and they were supposed to get married, and she, like, bailed on him, like, right before. And it was like this huge embarrassment in the press. And all his friends were just horrified when he took her back. But that was kind of his pattern. I feel like that's what he felt he had to do to win.

[Lee Eisenberg]

You know, one of his wives had left and come back. And then on the COVID of Playboy, he made her Runaway Bride.

[Holly Madison]

Yeah, yeah, that's the one.

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[Lee Eisenberg]

So you leave and what is that time like? Is it slowly dawning on you that you need to see what happened in the mansion in a new way? Like, what was it like when you left?

[Holly Madison]

Um, immediately. I didn't see it that way. I didn't want to think about it. I wanted to tie it up in this nice, neat bow and just move on with my life. The patterns I'd seen when I was at the mansion were most of Hef's ex girlfriends. Not everybody, but most of them would come back for events, and he'd be excited to see them and give them a big hug and they'd be welcome back and all this stuff. So that's kind of what I thought would happen for me, just because it's the pattern I had seen. So I didn't want to think about it. Anytime anybody would ask me about the show or fans would come up and ask, oh, how's Hef doing? How's so and so doing? I would always say nice things because that seemed like the nice thing to do. And I didn't really want to think about it. I was more concerned about hitting the ground running and creating a life and career for myself. It wasn't until maybe like, four years after I had left, I'd wanted to post an Instagram photo of a certain outfit I had. And to find that photo, I had to look back at this coffee table book. We'd made, like, a girls next door coffee table book. And I was looking through it, and I don't think anybody else would be able to tell by looking at the photos, but I can tell because it's me. I was like, holy shit. I'm like, fake smiling in all of these, and I'm so miserable. And that kind of brought it all back. And I sat with that for a while, and it was a couple more years of just fans coming up to me out in the world every day saying, oh, my God, do you miss the Mansion House, Hef? You guys were so cute together. And I'm still, like, saying the nice things. Cause I think that's a nice thing to say, but I'm lying. And when you're lying that much, it starts to, like, eat away at your gut. You don't want to do it anymore. And I'm just like, okay, I just need to write a book and, like, air this all out so nobody ever asks me how Hef is again.

[Lee Eisenberg]

So I think a lot of people were pretty shocked by what you described in the book. And it must have changed how people talk to you about your time in the Mansion after. What did that feel like when you sort of lay all this out? And then people are like, oh, I had no idea. Oh, my God. Like, this is an abusive situation. This is a situation in which women are describing being sexually assaulted. This is a situation where women feel like they are captive. They feel like they can't leave, that they've been, you know, a term that we would use later as a groom, like, to be there. Was that. What was that like? When you kind of put this forward and let people know what it really was, what the experience was really like for you?

[Holly Madison]

It was a Huge relief, because I could finally be honest, and I felt understood and seen by some people, not by everybody. I mostly got attacked when the book came out because this was back in 2015, so, like, the MeToo movement wasn't mainstream back then. People didn't have a thought as to why. Like, a casting couch could be problematic. People were just like, fuck you, bitch. You wanted to be there. You know, why didn't you leave? You know, that was kind of the stuff I was getting. But I think people understand better now, and I think especially the younger generation is more open to just hearing people's stories and knowing that there's nuance to stories and that it's possible to want to get into a situation and then get there and realize you are in way over your head. And now what the fuck do you do, you know?

[Lee Eisenberg]

Yeah, I was gonna bring that up. So. So Hugh Hefner dies in September of 2017. And in part because of the book that you wrote, a few other people had begun speaking out in obituaries. There's this reflection of, like, hold on a second. We had treated this man like he was an icon of liberation, but that came at the expense of a lot of young women's independence, self worth, lives. What did you feel in that moment when he died? What was your reaction?

[Holly Madison]

My personal reaction. I mean, my experience with him was so specific. It's hard for me to look back on, like, his legacy or his whole life and just come to one, like, neat little conclusion. But I just remember at the time how it affected me personally was everybody wanted me to make a statement, and I'm like, I don't feel like that.

[Lee Eisenberg]

And you didn't. I thought that was cool.

[Holly Madison]

You did it.

[Jon Lovett]

You didn't say a fucking thing. That's cool.

[Holly Madison]

Which I think aside from my situation or any situation like it, I think it's kind of gross that people are expected to mourn publicly. Like, I was disconnected from him. I hadn't spoken to him in years. So it wasn't probably the emotional impact people might think. But what if you really did lose someone so close to you and you're expected to just come out and talk about it on social media within a week? Like, that's gross. So that's just a weird phenomenon, period. But, yeah, I didn't say anything.

[Lee Eisenberg]

And then one week later, I didn't realize this timing. One week after Hugh Hefner dies, the New Yorker and the New York Times publish exposes around Harvey Weinstein's abuse of women, around the casting couch that Sets off, obviously, the MeToo movement. That must have been. It must have brought up a lot for you when this was unfolding. And all of a sudden, women are telling their stories about ways in which they felt like a powerful man had either coerced them or abused them in some way. Like, how did you see your experience fitting into, like, me, too, as it was unfolding?

[Holly Madison]

Well, my situation isn't the same as a lot of people's. I don't want it to get mixed up with, like, say, a violent rape or something like that. But I was just so glad that women were finally able to be listened to and have a voice. I have a close friend who was raped by Harvey Weinstein, and she told me about that years ago. So I knew this kind of thing was going on. So I was just relieved that it was all brought to light, really.

[Lee Eisenberg]

But there are, like, just having listened to you and Bridget talk about it, the way she describes the first time she had sex with Hugh Hefner, it is, at the very least, in a gray area of someone who's, like, all of a sudden having sex with this man in a way that they were quite surprised was happening. There are others that have accused him of sexual assault. Like, even now, like, do you think we still, as a society, gloss over some of the ways he mistreated women? Are we still attached to the kind of glamorous version?

[Holly Madison]

I mean, when Secrets of Playboy came out on A and E, I think in 2021, I think a lot of people paid attention to that. But I do think there's a danger of it kind of getting glossed over again. I mean, even on our podcast where we talk about girls, like, we try to include everything. We try to include, like, the good parts of being on the show, and, you know, what we did learn and gain from it, as well as the bad things. But I do worry about that. I do worry about just people being fascinated with the aesthetic and just the whole time period. And, you know, I was always so fascinated growing up with, like, old Hollywood. And, you know, the more morbid the story, the better. You know, the more salacious undertones, the better. And I know there's probably, like, a new generation who probably looks back on my story and sees the same thing. So I just hope that it doesn't get glossed over again, you know?

[Lee Eisenberg]

Yeah. And I think people can handle a complicated scenario, and I think you talk very openly about people as being fully complex, have a lot of qualities.

[Jon Lovett]

But.

[Lee Eisenberg]

There is a way in which it felt like what Playboy Represented was like, that liberation had to come at the expense of women. That the only liberation was, like, in order to live in a sexually liberated society, it was one in which men were still gonna have the power. And I wonder if even now we have, like. I think we still in some ways, live in that world where we're still kind of. There's the conservative model that requires women to be a certain way. And if you don't want that, well, you have to build an alternative. And it seems like we're still grappling with the option that isn't the Hefner style kind of sex without consequences.

[Holly Madison]

Yeah. I think one thing that people don't hold a lot of space for still is just the emotional impact sex has on women. A lot of times it's a biological thing. Granted, not everybody's the same. I'm sure there's a lot of women out there who can fuck like a man and not think about it the next day. And I wanted to be that person. When I was young. I, you know, in the culture I was raised in, just pop culture in the 90s, that was kind of where everything was headed. Like, women should be able to just have sex like a man and not care, and who cares? But that's not the reality. You know what I mean? Like, I can't have sex with somebody and not be, like, severely emotionally impacted by it. It's just a thing. Right?

[Lee Eisenberg]

Well, I've actually, like, I'm a gay person. And I. I've often thought that in the gay world, there's an assumption that all the men have that kind of male version of. Of what it's like to not have an emotional attachment to sex. But I actually think in part because being gay is in some ways feminine, there are probably maybe more gay guys who are like women in the sense of feeling really emotionally attached to sex. And in that world, that's not really something people. It's assumed that people have this sort of completely detached psychological relationship, but it's not. Not the case. And I do think we struggle with that. Like, how to talk about that when it means that, like, sex sometimes has just a greater emotional toll for women. Even if everybody is free and equal and making their own decisions.

[Holly Madison]

A hundred percent. Yeah.

[Ad Read Host]

Hey, don't go anywhere. There's more of Love it or Leave it coming up.

[Jon Lovett]

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[Lee Eisenberg]

That's so cool.

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[Jon Lovett]

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[Lee Eisenberg]

Holiday because right now Mint Mobile is.

[Jon Lovett]

Offering you the gift of 50% off unlimited. To be clear, that's half price, not half the service. Mint is still premium unlimited wireless for a great price. So that means half day. Yeah.

[Lee Eisenberg]

Give it a try. @mintmobile.com Switch upfront payment of $45 for.

[Holly Madison]

Three month plan equivalent to $15 per month. Required new customer offer for first three months only.

[Jon Lovett]

Speed slow.

[Holly Madison]

135 gigabytes of network busy. Taxes and fees extra. See mint mobile.com.

[Lee Eisenberg]

Do you feel like post me too or just with time that that effort to kind of hold you responsible for all the ways in which this was harmful. Like, is that changing?

[Holly Madison]

Oh, 100%. I feel like for the past, you know, six or seven years, people have been so much more open to hearing my story and understanding and I feel seen and heard.

[Lee Eisenberg]

What is that?

[Holly Madison]

Like, amazing. And there's. And you have to understand too, and this is something everybody can take away is not everybody's gonna get you. Like, Bridget and I were just talking about this the other day. Sometimes you can say something and then somebody will comment online and they're trying to say you said the opposite of what you said. Do you ever have that happen to you?

[Lee Eisenberg]

It's incredible.

[Holly Madison]

It's insane.

[Jon Lovett]

People.

[Lee Eisenberg]

It's people. And also just people taking the like, least generous interpretation of your point. Like, or saying like, I can't believe you're complaining about this when so and so has had it so much worse.

[Jon Lovett]

What about them?

[Lee Eisenberg]

It's like, well, I'm not talking about them. I'm not saying this is the worst thing that's ever happened to anybody in.

[Jon Lovett]

The history of planet Earth. You're just describing your own experience.

[Holly Madison]

Or sometimes people think because you cross the threshold into like being famous or having money, that that means you can't ever complain about anything that happened to you or talk about it in a negative way or, or talk about in a way where somebody else could take value from that story, which is silly.

[Lee Eisenberg]

Do you ever miss the time in the Playboy Mansion? Do you ever look back on aspects of it and think, well, I missed that part of it.

[Holly Madison]

There are little, little slices of it. But sometimes those tend to be things or most of the time those tend to be things where it was just like me and the girls getting to do something. Like there was a time on the show where we all took a motorhome and we went up to the Madonna Inn for Bridget's sister's birthday. And that was just such a fun night just to be away with the girls. So it's always kind of stuff like that it's, like, stuff where the girls just got to be by ourselves and have a girls day.

[Lee Eisenberg]

It's been interesting listening to you and Bridget on the podcast because you're so thoughtful and you're such a smart and conscientious person, and it's interesting. And you're precise, too. Like, you're a very precise way of speaking, and there's moments where you'll catch yourself and you'll correct it to make sure it's exactly accurate. And, you know, you're a young person and you have this idea of, like, how you're gonna make it, and it's gonna be this Pamela Anderson path or the Carmen Electras and those people. And those are paths that started with how you looked, that started with the fact that you're beautiful. You must have been told you were beautiful from the time you were a little girl.

[Jon Lovett]

Right?

[Holly Madison]

I mean, my mom would. I think she was being nice. I think I knew I had potential to be beautiful. I think I thought, oh, if those makeup artists at Playboy could just get their hands on me, I'd be so hot. Like, that. I wasn't, like, thinking I was already hot. It was more like that. Like, I was always told I was smart from a young age.

[Lee Eisenberg]

You were. You were.

[Jon Lovett]

You were like.

[Holly Madison]

Yeah, I was always the kid that was, like, put in the gifted class and got the best SAT scores and stuff like that. So it's kind of the thing where, like, a beautiful woman wants to be told she's smart, but a smart woman wants to be told she's beautiful.

[Lee Eisenberg]

But you were both.

[Holly Madison]

Thanks.

[Lee Eisenberg]

But so, but, but, but then why. But, like, that's what I'm trying to like, of all the paths to like. So Pamela Anderson is on Baywatch at the time, roughly this time, like, when I was growing up. And it was. It was part of the story that she started here, and that's how she got there. Look, what made you think that was the way for you? Like, there was a bunch of different ways you could have made it. Right. You were in the gifted classes. You could have. You were pursuing an education. Like, what made you think that this was, like, basically a route through how you looked?

[Holly Madison]

It's hard to explain other than it was kind of this innate want that I wanted to experience, that for whatever reason, I would see these images on TV and, oh, my God, these women are so beautiful. And I always had this fascination with old Hollywood and Marilyn Monroe, and I always felt like I wanted to experience that. And I think as a kid who had trouble Connecting with other people. I think I thought that fame would be a shortcut to connecting with people, which. Spoiler alert, it's absolutely not. Fame does not make you feel loved in any way. But as a kid, I think I thought that, and I think that's kind of of what pushed me in that direction. So I think I just wanted to experience that life for whatever reason. Like, I wanted to be seen as sexy, and I wanted to be in Playboy, and then I wanted to have some kind of a career in the entertainment industry.

[Lee Eisenberg]

Do you think it was because you were on the spectrum that you could see a path that involved your beauty, but maybe one, not one, involved your personality and your intelligence? Because it is. Of all the things to choose, it's a very specific thing because it's not as though there was the Internet where you could dial up all these different options. You had to go out and seek Playboy. You had to know what it was and go find it. And if you were a kid, nobody was gonna give it to you. Right. It was kind of a forbidden thing.

[Holly Madison]

Yeah. Yeah. That's a really interesting question, because when I was younger and picturing myself, like, being famous or being seen or being in Playboy or whatever, it was really all about the appearances and what kind of fun clothes I can wear and things like that, and. And can I be seen and known. I wasn't really thinking about how my intelligence was gonna play into it, other than I thought it might help me make it there, period, you know?

[Jon Lovett]

Do you feel seen now in some.

[Lee Eisenberg]

Way outside of being part of Girls Next door?

[Holly Madison]

I do, 100%. Like, I know it's still, like, the predominant thing people remember me from, but I think people know my story, too. I think it's hard for people to know who I am at all without knowing the story I've told and what's come after. So that's satisfying.

[Lee Eisenberg]

What are you hoping to do next? You're sort of revisiting this chapter of your life, but what are you hoping for in the coming years?

[Holly Madison]

I have a couple of true crime shows on ID Network, which I would love to keep doing. Those. I love those. I live in Las Vegas most of the time, and I really love the community there. I'd love to be, like, more involved in the community. When I first moved there, I was like, I'm going to be mayor of Las Vegas one day. So something like that.

[Lee Eisenberg]

That's a great idea. Idea.

[Holly Madison]

I'd love it.

[Jon Lovett]

What would you do to make Las Vegas great again?

[Lee Eisenberg]

No, don't answer. But What? What, What? If you were the mayor of Las Vegas, what would be your platform right now? What are some things you think that the government of Las Vegas should be doing better?

[Holly Madison]

I don't know. Well, it's actually really tricky the way it's divided up, because if you're the mayor of Las Vegas, you're only the mayor of, like, downtown.

[Lee Eisenberg]

Right. Because it's unincorporated.

[Holly Madison]

Yeah. So then you have the whole entire strip, which is so much a part of what Las Vegas is. So I don't know how much control you actually have over anything, But I think what the community is really concerned with right now is just affordability for tourists. Everything is just so expensive. And I've noticed people are starting to make changes and offering, like, the $1.99 huge margaritas again. And, you know, they know that that kind of thing is what's going to bring people back. So I think that's the direction the city's going.

[Lee Eisenberg]

So, last question. There was a, like, archives of photos, and Hefner kept all these diaries and this little black book where he took notes on everybody. Playboy had all kinds of pictures of you and all this stuff that belongs to you that you never signed over.

[Holly Madison]

Yeah.

[Lee Eisenberg]

And that now belongs to this estate, I guess. Have you ever thought about trying to get it back? Of trying to take back what you had never contractually given over to them in some way? Like, have you thought about what you are still owed, even all these years later?

[Holly Madison]

I don't know about what I'm still owed, but I would absolutely sue them if they tried to put those scrapbooks in, like, a library. Because I found out while I was there that that's what he wanted to do with his extensive scrapbook collection. And I was horrified because, you know, he takes nudes of all these girls who come upstairs when they're just completely wasted. Probably don't even know what they're doing. He puts, like, their full name in the caption. It's horrifying to think that that would just go to, like, a library. And that's not where they are now. They're in the control of his foundation, and his ex wife is in charge of that, which is weird. So they're, like, locked away in a salt mine somewhere. But if they were to be put anywhere publicly or, like, scanned and put online or put in a library, I absolutely would sue. Not just because of me, but because of every other girl who doesn't even know she's in there because she took too many Quaaludes or whatever, and you.

[Lee Eisenberg]

Have any lawyers then, but you got lawyers now, right?

[Holly Madison]

Yes.

[Lee Eisenberg]

Yeah, yeah. How do you have so many fucking Quaaludes? They stopped making them in like the 70s.

[Holly Madison]

I think there was a stockpile because on Secrets of Playboy, they tell a story. They talked to a woman who was a 19 year old secretary of his at the time and a woman who was his 19 year old girlfriend at the time, and he would get these prescriptions of Quaaludes and he would take them out under different people's names. Like, it wouldn't. So he could get more. It wouldn't just be his. It would be like he put his secretary, she's getting a prescription, but he's really getting that his girlfriend's getting a prescription, this other secretary's getting a prescription, you know, so he just had this stockpile.

[Lee Eisenberg]

Cause I believe it was. They stopped making it in the 1980s, I think so. So how many. What's it. There's some secret, like, Vault filled with 1980s Quaaludes that he was giving out for years after. Yeah, that's.

[Holly Madison]

Have you seen that scene from Wolf of Wall street where he's like taking the old expired Quaalude, right?

[Lee Eisenberg]

He was giving out these Quaaludes.

[Holly Madison]

Yeah. It's not funny. I don't know why I'm laughing.

[Lee Eisenberg]

It's not funny.

[Jon Lovett]

It's.

[Lee Eisenberg]

Well, I think. What's so.

[Jon Lovett]

What's so.

[Holly Madison]

It's just absurd.

[Lee Eisenberg]

Well, it's absurd that, like, I was struggling with this because I, like, I grew up in the 90s and Hugh Hefner was then, like, he was on Cribs, right? Like, he was this like, larger than life figure that was like, so cool.

[Jon Lovett]

It was cool.

[Lee Eisenberg]

The Playboy Mansion, the Playboy Bunnies. And like, obviously it's your experience, but like, just as an outsider seeing it, it's like, oh, this is a monster. This is a monster who has abused, I don't know how many girls who were vulnerable and kind of beholden to him. And someone who, like, even if you don't see it as the same, as sort of a forcible rape, was coercive and have women having sex night after night who did not want to and woke up feeling bad about it the next day. And even still there is this sort of ambivalence about him. He's calling these drugs that he's giving to young girls thigh openers. Like, are we talk. Aren't we. Isn't this a monster? Like, aren't you talking about the time you had to live with a monster and that even now you are trying your best to see it in a way that doesn't kind of hurt as much. But that for all the good qualities and nice moments, this is a monster.

[Holly Madison]

Oh, yeah. I mean, even when I look back at, like, good qualities and nice moments, to me it seems very artificial. Like, even before I really faced what my time at the mansion was like and really dove into it emotionally, Like I was telling you for like the first four years I left, like, I was still doing a spinoff under, like, this executive producer who was close with him, and he was always like, you know, why don't I just get you on the phone with Hef? Let's just you guys talk. And I absolutely refused to do it. I didn't want to do it. There were a few scenes I did for my show to like, go, congratulations, you're getting married. You know, things like that. But he would always want me to have like this one on one conversation. And I didn't want to do it because I felt like I'm going to be talking to a robot. Basically. Like, this is somebody who's just so manipulative and is just going to say whatever he can say to me to get the reaction he wants back. It would feel like such a fake conversation. So even then, before I'd really processed everything, I was like, no.

[Lee Eisenberg]

And do you have any, like, what's your advice to anybody out there that feels stuck in that kind of circumstance?

[Holly Madison]

Lean into yourself and don't be afraid of what other people are going to think. I think I was afraid to speak out for so long or afraid to make a move or try anything different because I felt so strongly that everybody was so judgmental against me and thought I was a bad person or, you know, that I was a whore for being there or whatever, and I just let it make me miserable. And I would just encourage people to not make fear based decisions and just, it's never too late to step out or find something new for yourself.

[Lee Eisenberg]

Holly Madison, thank you so much for taking the time to talk. And I hope everybody checks out the podcast. And I think it's actually like an amazing thing that, you know, here you are in 2025 and you have kind of lived through all these eras and survived being attacked all along the way. And now we're finally, at least hopefully in a moment where people are able to hear you without wanting to hold you responsible for what was a really ugly and misogynist environment. So thank, thank you for being here.

[Holly Madison]

Thank you so much.

[Jon Lovett]

If you're already scrolling endlessly, which we know you are.

[Lee Eisenberg]

Don't forget to follow us at Crooked media on Instagram, TikTok and all the.

[Jon Lovett]

Other ones for original content, community events and more. You can also find Love it or leave it on YouTube for videos of your favorite segments and other YouTube exclusive content.

[Lee Eisenberg]

And if you want to type our.

[Jon Lovett]

Praises or rip us in new one, consider dropping us a review. Finally, you can join Crooked's Friends of the Pod subscription community for ad free.

[Lee Eisenberg]

Love it or Leave it and Pod.

[Jon Lovett]

Save America episodes, subscriber exclusive pods and more. Sign [e-mail] friends love it or Leave.

[Lee Eisenberg]

It is a Crooked Media production. It is written and produced by me, John Lovett and Lee Eisenberg. Kendra James is our executive producer, Bill.

[Jon Lovett]

McGrath and Caroline Reston are our producers.

[Lee Eisenberg]

And Kennedy Hill is our Associate producer. Hallie Kiefer is our head writer.

[Jon Lovett]

Sarah Lazarus, Jocelyn Kaufman, Peter Miller, Alan.

[Lee Eisenberg]

Peer and Suba Agra all are our writers. Jordan Kantor is our editor, Kyle Seglin and Charlotte Landis provide audio support. Stephen Colon is our audio engineer. Our theme song is written and performed by Cher. Sure. Thanks to our designer Sammy Cadearna Ries.

[Jon Lovett]

For creating and running all of our.

[Lee Eisenberg]

Visuals, which you can't see because this is a podcast. And thanks to our digital producers David Toles, Claudia Shang, Mia Kelman, Delon Villanueva and Rachel Gajewski for filming and editing video each week. Our head of production is Matt de Groat, and our production staff is proudly unionized with the Writers Guild of America East.

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