Chapter 1: What insights does Holly Madison share about her first visit to the Playboy Mansion?
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Chapter 2: How did Holly Madison's experience at the Playboy Mansion differ from public perception?
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Chapter 3: What were the dynamics of living with multiple girlfriends at the mansion?
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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.
Chapter 4: What types of parties were held at the Playboy Mansion, and how were they perceived?
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 the City at the Playboy Mansion, you had not moved in yet. Is that correct? No, and I'm so bummed I missed out on it. I got the opportunity to do cameos on some pretty iconic shows there. We did Entourage and Curb Your Enthusiasm. Wow.
Just Missed Sex in the City, which is such a bummer because I'm such a big fan of it. We watched that every week when I was at the mansion. You did? Yeah, we did. Hef was a huge fan of it. Yeah, it's so strange because the whole experience for me and for us in general was very surreal, very strange.
Chapter 5: How did filming 'Sex and the City' at the mansion impact Holly's view of the experience?
Hef 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. 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, 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 like, 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? Yeah. Oh yeah.
Did you feel that? Yeah. I mean, that episode came out in 2000 and Hef 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.
Chapter 6: What were the day-to-day activities like for Holly and the other girls at the mansion?
And when I got invited to my first one, I was so excited. It was just such like a bucket list thing. Yeah. And how did you get invited? 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 was super excited. Yeah. And was this one of the like pajama parties? 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.
Chapter 7: In what ways did Holly feel conflicted about the portrayal of women in the Playboy brand?
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 Night's party. It was just some vague party.
When you watch the episode, did you think like, oh, that's accurate or though that's totally inaccurate? Or what were your thoughts? 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' 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 parties.
Chapter 8: What reflections does Holly have on empowerment and sexuality in the context of her experiences?
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. Interesting.
And then, so in our scenes where 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 were in the show. One was that we had this scene where we were walking in 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 it?
Regular life there, like versus a party or when people would come, you know, regular life, 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'm going to give people a tour of the grounds or whatever. And then one wing of the house was offices. So that's where Hef 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, you know, there would be different activities every night, a week, like a couple of nights a week, like Wednesday and Friday have would take us out to nightclubs Wednesday night. Yeah. 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 to do on Monday. And then Tuesdays, we would usually play like board games or something. So it was a whole variety. Wow. All over the place. Yeah.
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? 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.
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