Inside The Playboy Mansion with Holly Madison...

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Are You A Charlotte? 44 min 3 speakers 8 chapters transcribed
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What insights does Holly Madison share about her first visit to the Playboy Mansion?

Unknown 0:00
This is an iHeart Podcast.
Kristen Davis 0:02
Guaranteed human. In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever.
Holly Madison 0:15
I said, I need you to tell me exactly what you're doing. And immediately, the mask came off.
Kristen Davis 0:23
You're supposed to be safe. That's your home. That's your husband. Listen to Betrayal Season 5 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
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1969, Malcolm and Martin are gone. America is in crisis. And at Morehouse College, the students make their move. These students, including a young Samuel L. Jackson, locked up the members of the Board of Trustees, including Martin Luther King Sr.

How did Holly Madison's experience at the Playboy Mansion differ from public perception?

Unknown 0:50
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I'm Bowen Yang. And I'm Matt Rogers. During this season of the Two Guys, Five Rings podcast, in the lead up to the Milan Cortina 2026 Winter Olympic Games, we've been joined by some of our friends. Hi! Hey, Elmo. Hey, Matt. Hey, Bowen.

What were the dynamics of living with multiple girlfriends at the mansion?

Unknown 1:53
Hi, Cookie. Hi. Now, the Winter Olympic Games are underway, and we are in Italy to give you experiences from our hearts to your ears. Listen to Two Guys, Five Rings on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Kristen Davis 2:13
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.

What types of parties were held at the Playboy Mansion, and how were they perceived?

Kristen Davis 2:54
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.

How did filming 'Sex and the City' at the mansion impact Holly's view of the experience?

Kristen Davis 3:36
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?
Kristen Davis 4:28
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.

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