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Kristen Davis
This is an I Heart Podcast Guaranteed Human Thrive Cosmetics is all about amplifying your everyday look with products that work with your skin, not against it. Everything is 100% vegan, cruelty free and made with clean skin loving ingredients. Amplify your everyday go to thrivecosmetics.com Charlotte for an exclusive offer of 20% off your first order. That's Thrive Cosmetics. C-A U S E M E T I C S.com Charlotte before all the algorithm fed blah and the endless sea of dupes, shopping used to feel more fun. But here's a confession. Are you a Charlotte listeners? You can find that fun feeling again on ebay. It's not mindless scrolling, it's a fashion pursuit. I went on ebay to find a vintage Mugler jacket for the end of one of the seasons of and just like that where Charlotte had to look fantastic at the gallery and I found the most fantastic jacket there. So there's always more to discover. Ebay has millions of pre loved finds from hundreds of brands backed by ebay. Authenticity guarantee eBay things people love Winter is in full swing and Aleve is here to keep you moving. When the cold weather sets in, everyday aches and pains can linger. But Aleve's got your back with up to 12 hours of body pain relief per dose. Aleve keeps you going with long lasting body pain relief to get you through whatever the season brings. Chilly days or cozy nights. Aleve gives you that long lasting body pain relief you can count on this winter trial used as directed for minor aches and pains.
Holly Madison
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Kristen Davis
Hi, I'm Kristen Davis and I want to know are you a Charlotte? Hi everybody, welcome to Are you a Charlotte? Today we have the lovely Holly Madison who is going to talk to us about the LA episode where we film at the Playboy Mansion. She has obviously a lot of insight and she's a television Personality. You may know her from Girls Next Door, and she's also a New York Times bestselling author, which I love, and she has a lot of fascinating things to say. So enjoy this conversation with Holly Madison. Okay. This is very exciting. I'm so excited to talk to you. We've never talked before. I didn't get to meet you back in the day. But also, from what I understand, when we filmed Sex and City at the Playboy Mansion, you had not moved out yet. Is that correct?
Holly Madison
No. And I'm so bummed I missed out on. I got the opportunity to be do cameos on some pretty iconic shows there, like we did Entourage and Curb youb Enthusiasm. But I. Wow. Just missed Sex in the City, which is such a bummer because I'm such a big fan of it. Like, watch that every week when I was at the Mansion.
Kristen Davis
And you did.
Holly Madison
Yeah, we did. Hef was a huge fan of it. Yeah.
Kristen Davis
It's so strange because the whole experience for me and for. For us in general was very surreal. Very strange. Half was very nice to us. Like, really sweet and very, like, almost like your uncle or something, you know, Like. Like, it was hard to believe that he was him.
Holly Madison
Yeah. Yeah. I mean, that's how he comes off to most people. I mean, that's the person that I fell in love with. Obviously my situation grew a lot more complicated, but, you know.
Kristen Davis
Yeah, it's interesting because, like, I also feel. And I personally had, like, such conflict, internal conflict about filming there and making it seem kind of like fun and light, I guess would be the word, which is not. It's not like the vibe that I personally had about. About Playboy, though. At that point in time, things were getting like you guys were very mainstream, you know.
Holly Madison
Oh, yeah.
Kristen Davis
Did you feel that?
Holly Madison
Yeah. I mean, that episode came out in 2000 and have had been like, you know, he got. Got separated from his wife a few years earlier and started having the parties at the Mansion again. And those were. You know, I always tell people, like, it's hard to believe, but those were like the cool parties in LA that you wanted to go to that were super hard to get into. And when I got invited to my first one, I was so excited. It was just such like a bucket list thing.
Kristen Davis
And how did you get invited?
Holly Madison
I was working for Hawaiian Tropic, and at one of the events, Hef's doctor came to the event and he said, I want to invite all these girls to the party. So I'm super excited. Yeah.
Kristen Davis
And was this one of the, like, pajama parties?
Holly Madison
Yeah. The first party I went to was their biggest party. It was called Midsummer Night's Dream. They had that every August. And it was kind of this, like, fairy themed, like twinkle lights wonderland that they turned the backyard into.
Kristen Davis
And it was really cool. And when we filmed there, we go to a party. It's kind of slightly confusing because we arrive in the daytime, we're kind of wearing bathing suits. I don't know what the heck we were thinking in the costume department. I think we were confused. Right. But it wasn't supposed to be the pajama party or the Midsummer nights party. It was just some vague party. When you watched the episode, did you think like, oh, that's accurate or though that's totally inaccurate or what were your thoughts?
Holly Madison
It's pretty accurate. Like, I can't pinpoint, like you said exactly what party that was supposed to be. Like, it's a little bit like the fun in the sun pool parties. But there were a lot more people there in your guys's scene. A lot more extras. The fun in the sun pool parties would have, like, girls come up and like, enjoy the pool and everything. And Hef and his friends would be playing backgammon by the pool and some of his guy friends would be out on the tennis courts. But it wouldn't be very many people at all. Like less than 50 people. So they were pretty intimate. I would say the party I can compare the most to what you guys did was maybe like the 4th of July party, because that would be like a bigger daytime party. And then it would kind of move into a nighttime party. That's kind of. I think that's the only party they threw that was like that. That went from day to night.
Kristen Davis
Interesting. And then so in our scenes where we. We come in and I think that we filmed things that didn't end up in the show. At least I remember things that I don't think are in the show. One was that we had this scene where we were walking in and. And there were people, you know, girls in assorted small bikinis playing with bubbles. I don't know what the heck we were doing. But like, what. How. What was regular life there like, versus a party or when people would come, you know, regular life.
Holly Madison
It was pretty quiet during like a weekday. But at the same time it wasn't totally private like a home either. I started giving tours at the Mansion because they tours like a few times a week, like in the mornings on weekdays. And they would do it for like, contest winners or like military or people like that. And so I would kind of give people a tour of the grounds or whatever. And then one wing of the house was offices, so that's where half would go to work. And there was like a whole secretary staff down there. And then aside from his party, sometimes at night they would rent out the backyard for like corporate events and things like that. So that would kind of be like a whole separate world. So that was kind of the day to day life of the house for me and the other girls living there. We would just kind of during the day do whatever, you know, whatever. Shopping, errands, you know, some of us were still in college or going to school and things like that. We would do that. And then we had like a famous nine o' clock curfew. And no, there would be different activities every night a week. Like a couple nights a week. Like Wednesday and Friday, Hef would take us out to nightclubs. Wednesday night? Yeah, Wednesday night was a club night. Thursday night we would usually like go out to a restaurant. Friday was a club night. Saturday and Sunday he would have movie nights. Of course, Sunday during the day was a pool party. Monday he would gather with like his guy friends and watch a movie. He called that manly night. So us girls didn't really have anything.
Kristen Davis
To do on Monday.
Holly Madison
And then two, we would usually play like board games or something. So it was a whole variety. Wow. All over the place. Yeah.
Kristen Davis
That is so fascinating. I need to read your book. I need to read your book and get all the details because now I'm super interested. How many girls were there when you lived there?
Holly Madison
Well, during the last four years I was there, when we were doing the Girls Next Door show, it was just three of us. But when I first moved in, he was kind of in this Seven Girlfriends era. And that was just a nightmare. When I was there for that, nobody got along. And it was a constant revolving door. So it wasn't even the same set of seven girls when I first moved in as there was like three or four years later. So it was this cast of characters that was just all really competitive. And that was my least favorite time living there for sure. It was just a mess.
Kristen Davis
Yeah. When we, when we were there, there were. There were a bunch of girls. I mean, probably they brought extras and whatever in. I don't know. They were all obviously gorgeous and you know, whatnot. Wearing small clothing and we chatted with them, but not a lot. Like they kind of had. They. They would put them in a separate place and then we. Our place that we were supposed to spend the day was the game room. Oh, it was so weird.
Holly Madison
It is. It's a capsule out there. The game room was a whole separate, like, guest cottage on the property. And it was kind of this weird combination of, like, 70s arcade games and 80s arcade games. And then Heft's girlfriend in the 70s, Barbie Benton, had, like, decorated it, like, all old school, like, American antiques. So there was a weird mix of, like, American antiques and, like, 70s, 80s pinball machines.
Kristen Davis
Yes. And then there was this. Okay, that's so crazy that it was Barbie Benton, who, of course, like, you know, people of my generation know. There was, like, a pit, like a carpeted area with, like, a seating room. Yeah. What the heck was that?
Holly Madison
That was like a. Like a sex room on the side. And it had, like, a button.
Kristen Davis
Us, Holly.
Holly Madison
Yeah, it had.
Kristen Davis
Oh, no, the m. Yeah, we were scared. We were scared.
Holly Madison
Okay. So it had, like, a carpeted mattress floor with, like, pillows, and then there were, like, mirrored walls, and, like, the corners looked like mirrors. But then if you turned on a light, it would, like, the mirror would, like, disappear, and it would be like sex statues would be.
Kristen Davis
We saw the sex statues. We did see the sex statues. And we were like, why are we in here? Like, because it was a long day, right. So they were trying to find somewhere, like, theoretically comfortable for. We had a weird vibe in that room. So I think we tried to move.
Holly Madison
Yeah. A lot of people thought that house was haunted, too.
Kristen Davis
It definitely had a lot of, like, kind of dark energy, I would say. I mean, it's kind of a dark house as well. It's like an old dark house. But then, so. So, okay. Oh, God. It's giving me stress just thinking about it. But when we went, okay, so let's think about the party itself on film. And I don't know whose idea it was or. I feel like the guys in our world were really into showing all this, Right? Like, you know, in the way, you know, that they would be. And there's. So the grotto is, you know, part of. Part of it. And as the night goes on, you're like, none of the girls have tops on and whatever. Is this what would happen sometimes?
Holly Madison
Yeah, sometimes people would get a little crazier at night. But, you know, what was crazy about the parties is I always say that at the parties, I never saw anything too wild. I would hear about it, but, like, as a girlfriend, I would always kind of have to be seated at the table with half, which would be over by the dance floor. And believe it or not, people would be More on their best behavior in front of him because everybody wanted to stay on the list. They wanted to get invited back. So it would be more like I would hear from other playmates that like oh my God, I saw this in the grotto at 2am but that wasn't the stuff we would see really.
Kristen Davis
Got it. So what would good behavior be for half? Like meaning guys wouldn't be too aggressive with you guys. Not you, but the other non girlfriends. Is that like what was the like I, my, my thing that I felt upset about because they wanted us to all go to a pajama party in some kind of agreement about us filming there. And I was like, I am not going to that pajama party. I don't understand this. Like that seems a weird situation to put myself in. I felt worried. And also you had to wear some skimpy. What? I. I was just like I can't even get my mind around this. And I don't know if that was really silly of me or not. You what I'm saying, like what was the vibe in terms of the guy woman situation at the parties?
Holly Madison
I think for most guests, I mean obviously I've heard stories that aren't this too but I think for most guests it was okay. I think if you were really having a problem with somebody, they could tell you could tell security and they would have them removed. I mean I have to imagine having them removed would be easier for somebody who's more of an anonymous guy and maybe not like a big celebrity. But I think it was a pretty safe place for most partygoers. Again with the allowance that I've also heard that that hasn't been the case with some people, but I think for the most part most people had a good experience at the parties.
Kristen Davis
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Podcast Advertiser/Host
The show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete disclosures available at public.com disclosures.
Kristen Davis
So people did have a feeling of like I want to be here. I want to get invited back. I'm I'm. It's super fun. I'm sure there were drugs and but I'm still going to behave like as much as you know, like I'm not going to freak out. Well that's good to know because I didn't know what to think. I just remember all all the guys I knew wanted to go, you know and were it was seemed like you know, for them, like for the men. You know what I'm saying? That's why I didn't really feel like, yes, I would like to put myself in that situation, like, at the time. Yeah. But it was also very interesting to be there in terms of. I felt at the time, you know, it was very much held up as being empowering for women in some way. But I feel like we don't think of it that way now. That way, Correct.
Holly Madison
Yeah. I mean, I think that was what I bought into as well. When I went there is like, you know, I want to have this experience as, you know, being in the magazine and being seen as sexy and whatever. And I was just in, like, the deepest, deepest, like, inner. Inner ring where it really wasn't liberating anymore. But I think that was generally, you know, Playboy was accepted as like, this acceptable retro brand that, like, your dad grew up with and everything. You know, it seemed pretty tame at the time.
Kristen Davis
Right, right. It's interesting. It's interesting. But honestly, and this might be just, like, really too far, what I'm gonna say, we could cut it out. But, like, I thought my innocent little self, you know, when you guys did. Did. Cause at the time that we filmed, you weren't there yet. It wasn't the girls next door yet. And then when the girls next door happened, I thought it was all fake. Like, I just assumed you guys were not having to have sex with Hef.
Holly Madison
No. A lot of people thought that when I first, you know, moved into the group and, like, agree, like, go out with Hef and everything, I still wasn't clear on what was going on. Like, I'm like, okay, there has to be something going on. So I'm gonna go kind of check it out, see what it is. But I didn't know how much would be going on or it was very ambiguous because, you know, he'd be out there talking about how he takes Viagra all the time and these are all my girlfriends and things like that. But, like, people didn't really believe it. They thought, this has to be a publicity stunt.
Kristen Davis
I did not. Yeah, I did not believe it. So no one explained it to you? Like, no one said, this is what it is?
Holly Madison
No, not at all. Wow. Yeah.
Kristen Davis
So you just got sucked in, but little by little.
Holly Madison
Yeah, totally. I think when I talk about my situation and people were like, well, you knew what you were getting into. They're picturing that scene in Fifty Shades of Gray where she sits down at the table and she's given, like, this big contract about the consent and what's going to happen. And there's nothing like that up there. It is kind of Something you can get into, like, little by little and kind of like, lose yourself. It's very unstructured in that way.
Kristen Davis
Wow.
Holly Madison
Wow.
Kristen Davis
I'm sorry that that happened to you and all the other people, you know.
Holly Madison
Yeah.
Kristen Davis
And it was really held up as, like, you know, empowering for you guys and supporting you guys in your dreams. And, you know, he seemed so kind of just like, fuddy duddy ish, you know, I mean, he was wearing the weird clothes, but, like, I remember when he. He was filming with us, he was very nice, as I said, like in a kind of a uncle y kind of a way, and then up. And you were just like, he's so little and old.
Holly Madison
Yeah.
Kristen Davis
You know, but yet this other stuff was still going on, which just really blows my mind.
Holly Madison
Yeah, it was crazy, for sure. And I have to say, the scene you guys did there, the casting, was so spot on because they have so many female extras. And I recognize some of them. Some of them were playmates, some of them weren't. But the. And then they have a few men sprinkled in there. And the men are all super old. And the actor they have you talking to, when you're laying down on the pillows talking to that actor, he looks like. He so fits the part. Like, everything about his face and his teeth. Like, he looks like he would be one of Hef's buddies.
Kristen Davis
Like, I agree.
Holly Madison
How did they know?
Kristen Davis
I don't know. I don't know. I think they did a great job, too. And I. I had forgotten a lot of it. I. There's certain things I remember really well. Like, I remember the room that they put us in with the games and the psych statues. And I remember they kept trying to tell us that we wanted to go to the zoo, but I was so freaked out that he had wild animals there that I was like, no, thank you. I don't want to go to the zoo. Like, it's weird. Like, but everyone was very nice to us, obviously. But when we went to do the scene, I do remember being just so generally icked out. And I felt like that guy that I'm talking to wasn't even an actor. He just seemed fully. I mean, I'm sure he was, but, like, I felt like he was a guy that you would meet at a Hollywood party.
Holly Madison
Oh, he embodied it. Like, that guy was so good.
Kristen Davis
He really did. Too good. Too good. And I also didn't really remember what happened, which I often feel when I'm rewatching now because it's a while ago, obviously. And I remember the experience of filming more than the scenes and I thought, oh no, what is Charlotte doing? Don't talk to that guy. Ew. But that's good to know that you think we did a good job of casting it. That's good. Did you feel because, okay, so you watched this particular episode that aired in 2000 before you lived there, and then once you lived there, did you feel like oh yeah, Sexy City was pretty accurate or did you feel like no.
Holly Madison
I think I thought it was accurate for sure because it's just showing a party and it looked exactly like what a party would look like. Of course it doesn't capture everything about day to day life there, but it wasn't supposed to. It was just characters going to a party. So I thought it was super accurate.
Kristen Davis
Oh, that's good. Make every day feel Epic in the all New Hyundai Palisade Hybrid the Palisade Hybrid is packed full of features, cutting edge tech, up to an EPA estimated 619 miles of range on select trims and class leading interior space. The new Palisade Hybrid is redefining what it means to drive an suv. For starters, let's talk about interior space. It's class leading, which is just a fancy way of saying that the whole crew and everyone's going to be comfy. You've got seating for seven or eight passengers and yes, that available third row power seating that reclines. Game changer. There are available front and second row relaxation seats, basically a spa day on wheels and an available class exclusive blind spot view monitor that shows you a video feed of your blind spot right in the dash. How smart is that? There's even an available class exclusive built in dash cam. So whether it's a scenic drive or someone cuts you off and pretends like it didn't happen, you've got the receipts. And if you're all about the sound experience like me, the available Bose 14 speaker audio system is going to blow you away. I also love the tech forward touches like standard 100 watt USB C ports because fast charging is non negotiable these days and the standard passenger talk intercom that lets you chat with people in the back without yelling. Ah moms, you know what I'm talking about. Ready to upgrade your ride? Learn more about the Hyundai Palisade@HyundaiUSA.com Call 562-314-4603 for complete details. Before all the algorithm fed blah and the endless sea of dupes, shopping used to feel more fun. But here's a confession. Are you a Charlotte listeners? You can find that fun feeling again on ebay. Because on ebay it's not just shopping, it's a full on fashion pursuit. And when you find the thing that adrenaline hit is real. I went on to ebay to look for a super special vintage jacket for Charlotte to wear to the gallery and I found the most amazing Mugler jacket and the costume department loved it and it felt so good and I still have it at home. Like when you score that rare Adidas collab that's lived on your Mugler Mood board or the Dior saddle bag that you ripped right out of a magazine in 2007 and never got over. Yeah, those. It's about the thrill and the pursuit of finding those pieces that feel like you. There's always more to discover. Ebay has millions of pre loved finds from hundreds of brands backed by ebay. Authenticity guarantee eBay things people love Support.
Podcast Advertiser/Host
For the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor. Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete disclosures available@public.com disclosures if you're struggling.
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Kristen Davis
Isn't it weird to think that three HBO's shows film there, like Entourage, Curb youb Enthusiasm. I do not remember this. And us. That is bizarre. Yeah. Yeah.
Holly Madison
It's like. Like, everybody. It was crazy.
Kristen Davis
Do you feel like. And I don't know, this is probably. You know, I don't know if I should even say this, but, like, did we help to forward a kind of untrue narrative? You know, that it was glamorous and fun when it was really more than that?
Holly Madison
I wouldn't say an untrue narrative, because there was that side of it that was like that for sure. And I think that's the experience a lot of people had who didn't get deeper into it. But, I mean, it doesn't cover the whole thing. But I don't think it was supposed to. No, no.
Kristen Davis
I mean, it wasn't supposed to. But I. I do feel just some mixed feelings about the fact that, you know, our show, which is absolutely supposed to be about empowering women, and that was something that we felt really strongly about and really empowering and making space for all different kinds of sexuality, but freedom within that and, you know, consent and all of those things. And I remember at the time feeling uncomfortable about it, but that has a lot to do with how I grew up and my mom's opinions of it all, you know, very feminist and not into that. And then I remember later on feeling like, oh, maybe I was wrong. You know, like when. Because when you guys did the show, it did seem like you were somehow being supported or forwarding your dreams or, you know, it was. It didn't seem negative. Right. And I thought, oh, well, I'm glad for them. You know, that's how I felt at the time, of course, not knowing still the whole story, which you guys hadn't had the opportunity to tell. So I'm glad, number one, that you have had the opportunity to tell the whole story. Because I do feel like sometimes there's things in our business, maybe less so now, but in our world, the entertainment world in general, where it seems like, oh, this could be a good opportunity for you, and, yes, it involves your sexuality, but that doesn't mean that it's inherently bad. Right. But yet it's a slippery slope, a hundred percent.
Holly Madison
That's why I talk about it as much as I do, is I've heard, you know, Playboy doesn't exist in the same way as it did back then. But I've heard, you know, people tell me that they grew up watching Girls Next Door and thought it was so fun, so they thought the next best thing to get into would be porn. And now they regret it. So it's crazy the kind of effect those things can have. So that's why.
Kristen Davis
Yeah.
Holly Madison
About it. And love talking about, you know, what my motivations were and what I thought I was getting into and what it was really like, just so people kind of know what those situations are.
Kristen Davis
Yeah. I think that's great. I think it's so important and I'm so glad that you're okay. You're at a place in your life where you can do that and you can share that and you're. You've done the work on yourself to be able to share that without it being, you know, re. Traumatizing yourself.
Holly Madison
Thank you.
Kristen Davis
You're welcome. It's so important. And I mean, that's also one of the things that I think about when I look at the episodes, you know, did we unwittingly take part in also glamorizing something that maybe wasn't great for women? I don't know. You know, I don't know. It really was part of our culture, though, at that point in time. Yeah. So in that way I feel like. Well, it kind of makes sense. Right. And of course, we couldn't know everything that was going on behind the scenes because no one was talking at that point.
Holly Madison
Yeah. A hundred percent. Yeah. Just so harmless back then.
Kristen Davis
Right. Except when you were there, it didn't feel harmless. I did. I didn't feel the vibe. Yeah, yeah, yeah. I mean, they put us in the sex room, so yeah, we got the vibe. And I feel like the people that they hired, and it's interesting to. For you to say that you recognize some of them. I do feel like some of them. I feel like we're living there, you know, and we were. We were so fascinated, but we also didn't know. We didn't want to overstep our bounds in terms of like talking to people or asking them questions like what is your life like? You know what I mean? But we were there for a few days. It seemed like it was a while, you know, that we filmed and. And it didn't seem like they were just happy. Go lucky. Woohoo. We're living the life we want. It seemed like there was more stress.
Holly Madison
You know, I feel like I can almost see it on the girls. The twins he's dating, you know, the twins, yeah, they. They don't seem in a light mood, you know what I mean?
Kristen Davis
I do know what you mean. And that's what we felt. That's what we felt when we Were there, but yet we were supposed to be showing this glamorous. There was really no way to, you know, do a better job of telling the story. And also, no one was really volunteering any information to us either. Not that that was even our job. But like, for me, you know, when I go into a place I'm always interested in, you know, how do people actually seem like. Do they seem happy? You know, and at the time, it was such a. Like you said, I mean, those parties you would. Here, everybody went to those parties, you know, they were very much mainstream Hollywood. You wanted to go. I mean, not myself, because I was scared, as I said. But men in general wanted to go. And I feel like women wanted to go. I mean, I definitely know people who went and I don't. But they were actresses and I don't think anything negative happened, you know, because, I mean, you could go to any party in LA and people are going to hit on you. It's not shocking, obviously. And it. Yeah, Nothing worse than that. You know what I mean? But how.
Holly Madison
How.
Kristen Davis
Just curiosity's sake. How long did you live there?
Holly Madison
I lived seven years. Wow. Almost all of my 20s.
Kristen Davis
Yeah.
Holly Madison
Whoa, whoa. Wow.
Kristen Davis
Well, it's really great that you got out and that you're writing about it. Is there anything else that you want to talk about from the show or from the episode that I didn't touch on? I'm just so curious. Your own perspective.
Holly Madison
Yeah.
Kristen Davis
One thing I'm curious.
Holly Madison
Do you remember what the lead time on your show was like? How far in advance you filmed versus at that point?
Kristen Davis
Not far. It would have been just a couple months. Yeah. Because we would go back to work in February. We'd been pretending it was spring. Cause we always came on in June. And so by this point, I have the date here somewhere. We would have been filming and it would have been like maybe two, three months before it was on. So pretty quick. Pretty quick. We would have been there in the summer of 2000. It would have been on and it was on in September. So we would have been there in the middle. Yeah. And I do think that the Midsummer Night party was the week that we were filming, because we were all supposed to go, but I was like, well, no one asked me. I'm not gonna go. No one got. Am I okay? You know, and I was in some trouble because we had been apparently committed, you know, to do it.
Holly Madison
Did any of the cast go?
Kristen Davis
I think they all went. Oh, we would have to ask them. I think they all went to kind of like make an appearance and go, you know what I'm saying? I don't think they hung necessarily, but I think that they were good employees as opposed to myself, where I was like, my mother's gonna be really mad at me, you know, very Charlotte type of a situation. But, you know, I grew up with. They. It was just not thought of as empowering. Right. To be, to be, you know, outwardly sexual or whatever. But then I find myself on the show called Sex and the City. So, you know, it's all really interesting. But I do feel like, you know, it's an interesting thing to think about too, because obviously your personal experience and what you're going through is not good. And the fact that no one was upfront with you about it is even worse. Right. So like you're little by little, you know, pulled in. That's the worst situation, I think. And happens so frequently, unfortunately. But I do feel, and it's an interesting thing, you know, the openness about sexuality, I do feel is generally important for women.
Holly Madison
Oh, I think so too. Yeah.
Kristen Davis
And it's so hard to know when it crosses the line into not being empowering. It's a very interesting, interesting thing, I think.
Holly Madison
No, I think too.
Kristen Davis
Right. Because we can't just hide ourselves. There's no. Why should we have to hide ourselves? Like we're sexual beings, just like men are sexual beings like that. It's. It's unfair and, you know, inequitable to think that we can't. Right. But then there's so much danger in the world, you know, in many ways. Right? Yeah. So you want to be careful. It's an interesting thing to me. And I have a 14 year old daughter, so I think about these things. You know what I mean?
Holly Madison
I think so too. My daughter's 12 and.
Kristen Davis
Oh, wow.
Holly Madison
Yeah, I think, I think more discussion is better, honestly, because like, when I was young, kind of the trend was like. Or the way it was portrayed in pop culture was like, women should just be able to have sex like a man and not care. And, you know, that's empowerment. And I feel like nobody talks about like the emotional impact of sex.
Kristen Davis
Yeah, I agree.
Holly Madison
For some reason. And I think, you know, and of course, like females, we operate a little bit differently. Obviously there's outliers, but I think for most females, there's a huge emotional impact that comes with sex. And just people don't want to talk about that for some reason. They just act like everything should just be casual. They act like you should either be totally casual about it or you need to like, have, like, religious principles that keep you in line and nobody kind of talks about the in between. Like, well, why is it not so great? And how do you really feel?
Kristen Davis
That's so true. So true, Holly. I mean, I think it's super interesting, certainly when we're thinking about our daughters, too, because we have come so far in so many ways, and then in some ways, we still don't have total freedom to talk about anything freely that impacts us. Right. Like, why. Why is it not okay to talk about the fact that women are gonna potentially be navigating sex differently than men? That makes sense. Right. And maybe it's. Maybe it's not true. Right. Like, maybe there's a Samantha out there and she wants to have sex like a man and more power to her. Right, Right. But what about all of the kind of realities of it, you know? Like, the realities. And what do we say to our daughters? And, you know, I think it's important to think about that. My daughter, they still have sex ed classes that are about, like, consent and, you know, really important, interesting things that I certainly never. We didn't get anything like that. We were like, you're gonna get your period. Like, that was really it, you know, but. And I think it's so great. My daughter hates. Hates these classes, though. Yeah. She's like, oh, no. And I'm like, just. Just do it. Just do it. It's going to be useful information for sure. But it's so, so hard to navigate a hundred percent.
Holly Madison
It's really tricky. So I think the more discussion, the better, honestly.
Kristen Davis
I think you're right. I think you're right. Because really, really, you know, covering things and having secrecy just leads to bad badness, because then people feel like they can't talk and they can't say something that's true for them, or they can't report something bad that happened to them, or they can't. That's the worst. That's what we need to get rid of.
Holly Madison
Absolutely, yes.
Kristen Davis
When you look back and you see, like, if you were ever to just be flipping in or not that people flip. If you were ever to be streaming the episode of Sex of the City at the Mansion, was there, would you. Would you think, like, oh, and watch it where you'd be like, oh, no, I don't want to watch it.
Holly Madison
I mean, for me personally, like, I've already seen it and I like it, and I think it's fun, and I think it's like a fun glimpse into that era. The things I get triggered by more Personally, I mean, it's always surprising. Like, I do a rewatch podcast with one of my co stars from Girls Next Door and the show will hit a certain way. But then we did an episode where we talked about the movie the House Bunny with Anna Faris that.
Kristen Davis
Yeah.
Holly Madison
With the Mansion. And we had parts then. And it was weird because this was a very lighthearted comedy. But I told Bridget I'm, like, watching it on that movie, like, hit differently for some reason. Like, I never really know how it's gonna hit, but I think it's in the City episode because I wasn't in it and because it more captures the time period when I was just aware of Playboy as kind of an outsider. Like, I think I hadn't even gone to. I think that party that the rest of your cast went to was the first party I went to.
Kristen Davis
Oh, my gosh.
Holly Madison
Wow. So it more kind of captures the era where I still, like, only knew Playboy from the outside and was kind of fascinated by it. Like, I remember thinking the twins he was dating were so gorgeous. I remember seeing them at that party. So for me, it's more one of the ones I like. And you know what else I love? Random Is in the scene, you're wearing this bikini top that's like cherry print. A blaster in the past. Because I remember so specifically, like, that summer, like, the cherry print being everywhere. Like, I think Coach did a bunch of cherry print bags. And like, I was like, in downtown because I was, like, a broke college students. So I was, like, in downtown looking for all the fake Coach Cherry stuff.
Kristen Davis
I love it. Yeah. That was Shoshana. Do you ever remember the line Shoshana? That was Shoshana. Because Shoshana was cut for people with hips, which would be me. And there was always some stress when we would have, like, beach or bathing suit or whatever, because I, you know, I didn't know what the heck to wear. And Pat Field, our costume designer, was always unsure about me. And then. That's my own sarong I just tied on. Yeah. Yeah. Thank you so much. But I also think that we were fundamentally confused in that costume because we come in the daytime, but then it's nighttime. And were we supposed to get in the grotto? I don't even know. Like, to me, I watched that episode and I think, like, what. What were we doing? Like, what were we actually doing? I don't know, but it works. I mean, I love that picture of us with the four of us walking, walking in. And also because we are from New York, we Also don't really know, you know what. But, like, the characters aren't supposed to know what they're doing.
Holly Madison
Yeah. They are supposed to be a shout of water, so.
Kristen Davis
Yeah. Oh, I'm glad. I'm glad that you have a positive association when you watch it. That's good. That makes me happy. That makes me happy. Well, you are such a joy. Thank you so, so much. I have a pressing question for you.
Holly Madison
Yes.
Kristen Davis
Are you a Charlotte?
Holly Madison
You know what? Back in the day when Sex and the City was on and I watched it regularly, I was for sure a Charlotte. I identify as being a hopeless romantic and all that.
Kristen Davis
That.
Holly Madison
But as time goes on, I think I'm more of a Carrie. I've written a couple memoirs, so I identify as a writer. And also, like all the kind of like anxious, attachment style, cringe stuff that Carrie does has totally been me. Like, have you seen those edits where they do the three times she shows up in Big's doorway?
Kristen Davis
Love them so much.
Holly Madison
And the crop I'm. And the guy doesn't give up. That's been me so many. Oh, no, I think I'm really a Carrie. Wow.
Kristen Davis
I love it. I love it. I'm also kind of a Carrie. I'm like half Carrie, half Charlotte. And I do love those edits because there's just a way where you can see things from a different perspective. Where you're like, that is so embarrassing. You know what I'm saying?
Holly Madison
We've all been there.
Kristen Davis
We've all been there. And then the funny thing is, like, at the time that we were making the show, it never entered my mind that she should stop trying. I was like, of course.
Holly Madison
Yeah, he's the cooler.
Kristen Davis
Go in your crop. Yeah. Go in your McDonald's, you know, Le Big Mac, you know, whatever. I mean, it's all so interesting and I like the show in that way and that at different times in your life, you will look at it with different perspectives.
Holly Madison
Yeah, for sure.
Kristen Davis
I like that part the best, I think, because we all relate in different ways.
Holly Madison
Totally.
Kristen Davis
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Holly Madison
This.
Kristen Davis
Is an iHeart podcast. Guaranteed human.
Host: Kristin Davis
Guest: Holly Madison
Release Date: February 13, 2026
In this intimate episode, Kristin Davis welcomes Holly Madison—former Playboy Mansion resident, television personality (notably from Girls Next Door), and bestselling author—for a candid discussion about the surreal intersection between Sex and the City and Playboy culture. The conversation explores the filming of the iconic LA episode at the Playboy Mansion, the reality versus fantasy of life there, evolving attitudes toward female sexuality, and the complexities of empowerment, exploitation, and pop culture myth-making.
On the party invite mystique:
“When I got invited to my first [Playboy] party, I was so excited. It was just such like a bucket list thing.”
– Holly Madison (05:11)
On the reality of being a girlfriend:
“It was just a mess…nobody got along. It was a constant revolving door.”
– Holly Madison (09:15)
On the Mansion’s strange vibe:
“It definitely had a lot of, like, kind of dark energy, I would say. I mean, it’s kind of a dark house as well.”
– Kristin Davis (11:39)
On consent and ambiguity in the Mansion:
“People are picturing that scene in Fifty Shades of Grey…there’s nothing like that up there. It’s something you can get into little by little and kind of lose yourself.”
– Holly Madison (22:28)
On empowerment and regret:
“I’ve heard people…grew up watching Girls Next Door and thought it was so fun, so they thought the next best thing to get into would be porn. And now they regret it. So it’s crazy the effect those things can have.”
– Holly Madison (32:32)
On the evolution of empowerment:
“It’s so hard to know when it crosses the line into not being empowering. It’s a very interesting, interesting thing, I think.”
– Kristin Davis (38:15)
On the importance of open discussion for young women:
“The more discussion, the better, honestly…when I was young…the way it was portrayed…was like, women should just be able to have sex like a man and not care…and I feel like nobody talks about the emotional impact of sex.”
– Holly Madison (39:15 & 40:59)
On which character Holly identifies with now:
“Back in the day…for sure a Charlotte…But as time goes on, I think I’m more of a Carrie. I’ve written a couple memoirs, so I identify as a writer. And all the anxious, attachment style, cringe stuff that Carrie does has totally been me.”
– Holly Madison (44:20)
The episode is marked by honesty, nostalgia, and mature reflection. Both Kristin and Holly approach these personal, sometimes dark realities with warmth, humor, and mutual respect. They acknowledge the complicated legacies of both Sex and the City and Playboy, and the enduring importance of frank conversations about sexuality, agency, and media portrayal.