
#854: Join us as we sit down with Holly Madison – an American television personality, model, author, & entrepreneur best known for her role on the reality hit series The Girls Next Door, which chronicled life inside of the Playboy Mansion....
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Michael Bostic
The following podcast is a Dear Media Production. She's a lifestyle blogger extraordinaire.
Lauren Everts
Fantastic.
Michael Bostic
And he's a serial entrepreneur, a very smart cookie. And now Lauren Everts and Michael Bostic are bringing you along for the ride.
Lauren Everts
Get ready for some major realness.
Michael Bostic
Welcome to the Skinny Confidential. Him and her.
Lauren Everts
Holly Madison is on the show today. She is sharing personal experiences living at the Playboy Mansion. She talks, building her personal brand and the challenges of that. She also is telling us all about true crime. This episode highlights Holly's entrepreneurial ventures, her wellness routines, her beauty tips, and how she prioritizes her family. I personally am so excited to welcome Holly to the show. I have read both her books, down the Rabbit Hole and the Vegas Diaries. If you guys haven't read them, they. They are very juicy. I loved both of them and I also watched her on the Girls Next Door and of course, her own reality show, Holly's World. This episode showcases all different facets of her personality. I think you'll like it. Holly Madison, welcome to the him and her show.
Michael Bostic
This is the Skinny Confidential, him and her.
Lauren Everts
Taylor, are you excited for this episode? Don't get too excited.
Michael Bostic
Stay behind. Stay behind the glass back there.
Lauren Everts
I'm more worried. Holly Madison, why true crime?
Holly Madison
I've always been interested in those kinds of stories since I was a little girl. I grew up being obsessed with unsolved mysteries. That was always the thing I was hoping to catch on TV if my parents would let me stay up late and watch it. I've always loved kind of spooky, unsolved things like that. I've always been intrigued by it. Even One of my earliest special interests as a kid was old Hollywood. But I was always really attracted to the story that kind of had like a interesting and kind of like tragic ending, like all the movie stars that died young and all the mysterious things. So it was definitely something I was always interested in but never really pursued as a career in any way until this production company I'm working with, lion tv, brought this deck forward where they wanted to do a show called the Playboy Murders. And I was like, yeah, I don't want to do it. I've done too many Playboy things. It's like oversaturation at this point. And my agent was like, well, just look at the deck. Look at the cases. See what you think. So I looked at the cases, and all the cases in the first season pretty much were cases I'd never even heard of. And I thought I knew everything about anybody who was ever involved with Playboy. And I was reading through them and I was like, but this is a show I'd actually watch. So I was like, I'll do it. And I've loved being involved and loved being a part of telling the stories. This is our third season now.
Lauren Everts
So there's a thread with Playboy playmates who have been killed.
Holly Madison
Yeah. But it's not just as simple as that. It's a lot of people who are involved in the company, whether they were bunnies that worked at the clubs that were open all over the country to people who work behind the scenes. Like we're opening this season. There's a story of a woman who had a tragic death and she was working as a casting director for Playboy. And so it was a company that was operating. I mean, it's still a company, but in its heyday, it was a company that was operating for like 60 years. And there were so many people who worked for the company that you're bound to find all these interesting human interest stories. So we've got three seasons worth.
Lauren Everts
One thing about you that I think's really cool. I told you off air, I've seen all your shows, your books, your podcasts, Every time, every time you're on Heather McDonald's. Is that you? You have a lot of different interests.
Holly Madison
Yeah.
Lauren Everts
Like, you seem like a curious person.
Holly Madison
I'm very curious. Yeah. I'm all over the place. Anything from, like, health and wellness to unsolved mysteries to, you know, history. I love, like, niche history topics.
Lauren Everts
Have you been like that since you were little? What were you like as a little girl?
Holly Madison
Yeah, I was very imaginative as a little kid. I grew up in Alaska, like, almost off the grid. So it was a lot of, like, playing in the woods. And I would not have guessed Alaska. Yeah, I'm not gonna lie. Yeah, that's where I gre. And, you know, we had TV most of the time. So, you know, I would get lost in these kind of, like, Hollywood stories and tv, but also have this life where I'd be playing in the woods all the time and doing really, you know, things that felt very old fashioned. Like, I was really into the Little House on the Prairie books growing up because I felt like I could actually relate to that. My life felt more like 1880s than 1980s when I was a kid. So I've always been, like, all over the place and interested in different things.
Michael Bostic
What did your family do in Alaska?
Holly Madison
My dad worked in the timber industry. He was a port manager.
Lauren Everts
So you know what? I actually am not surprised that you grew up in Alaska.
Holly Madison
Really?
Lauren Everts
Because your skin looks so good.
Holly Madison
Thank you. So does yours.
Lauren Everts
Thank you. I didn't grow up in Alaska. I've had to wear a hat and driving gloves and all this stuff. Your skin looks so beautiful.
Holly Madison
Thank you so much.
Lauren Everts
And it's probably because it gets dark earlier there.
Holly Madison
Well, and also it's always overcast. It's always rainy. So I'm just not out in the sun. I wasn't like, my skin really didn't touch the sun very much growing up at all. And by the time I moved to Oregon when I was in junior high, but by that time I was already like into sunscreen every day and things like that. So when people ask me about my skin, I'm like, it's a million things. It's not just Botox, it's not just facials. I was on Retin a starting at like age 11. Cause I had acne and then like not seeing the sun throughout my childhood. I think that helped a lot too.
Lauren Everts
I mean, maybe we need to move to Alaska because it really is.
Michael Bostic
We'll just do like a big. Dear Media Alaska.
Lauren Everts
When you are living in Alaska and then you move to Oregon, what makes you want to come to la? Is it because you were like. You were into like the old Hollywood glamour of.
Holly Madison
Totally. That was part of it. But also my family and I would vacation every once in a while. We'd go down to Disneyland. And I always felt like on those trips, like everybody got along and everybody was so happy and everything was sunny and it just seemed like such an ideal place. And LA just seemed like a place where you could kind of make anything happen and there would be so much opportunity. Because, you know, back when I was growing up, there wasn't social media. There wasn't a way to kind of like get online and get noticed or make it happen for yourself. You had to do it the old fashioned way, move to a big city, go through all the gatekeepers. And I just wanted to go out and live this not ordinary life, which I ended up doing.
Lauren Everts
You definitely have lived a not ordinary life. So what's the first move that you made down here? Why did you decide to move? What broke the camel's back?
Holly Madison
Well, I always wanted to like the second I could get out. But I went to college the first two years in Portland and I transferred to Loyola Marymount in LA so I could get down there, down here. We're here today.
Lauren Everts
And you're also. You mentioned Disneyland. I don't think Michael understands. You might be a bigger fan than John Stamos who's a bigger fan?
Michael Bostic
I don't know. He's pretty up there.
Holly Madison
He is. I always say I was, like, the first Disney adult, but John Stamos, he's like, the one person I can think of who was, like, maybe there before me.
Lauren Everts
So when you move down here, you're in college?
Holly Madison
Yeah.
Michael Bostic
So what do you mean, Disney fan? Like, you, like, hang out there all the time, or you're just sort of, like, really into the Disney lore? Like, what do you.
Holly Madison
Yeah, when I. Even in college, I would go every once in a while and just, you know, I like to be at the park. So sometimes I'll go with a friend just for, like, a shopping and eating day. And I just love the atmosphere. I love the detail of it. I grew up on the Disney movies and the Disney cartoons. I'm just super into it.
Lauren Everts
I bet there's your good trivia with it, too.
Holly Madison
I think so. Yeah.
Michael Bostic
I'm back into it now that we have young kids. One time I tried. I grew up going there as a kid, and then I tried to go as an adult one time, and I walked in and I was like, man, it's kind of weird. I'm just standing around as an adult, like, by myself.
Lauren Everts
You tried to finger me in Disneyland in sixth grade.
Michael Bostic
I still might try.
Lauren Everts
You tried to finger wing me in sixth grade at Disneyland. That's a true story. So no wonder you have warm memories of Disneyland. I think you and Holly are talking about Disneyland.
Michael Bostic
That's why I have such great memories. No, but then I just went this last time as an adult, and I stood around. I'm like, I think it's kind of weird that I'm just standing here as a grown man. I had a corn dog and I left.
Holly Madison
Well, you know what's weird about it now is it's so crowded all the time.
Michael Bostic
Yeah, it's a lot.
Lauren Everts
It's really crowded.
Holly Madison
Oh, my God. Like, I remember back in the day, you could go in the fall, back when they. Before they started doing Halloween stuff on a weekday, and there would be nobody there. And you'd have the parks yourself. No lines on anything. Nobody there. There's no such thing as a not busy day.
Lauren Everts
Well, you go to Disneyland without getting, like, the plaid person.
Holly Madison
I get the guide if I'm there with my kids. But sometimes I'll go with my friends, and we're a member of the private club there, so we'll just go hide there and have food or just go and, like, shop and eat and keep it low key.
Lauren Everts
Hold on. You're a Club 55 member?
Holly Madison
Club 33.
Lauren Everts
Yeah, 55s in the south of Branch. Sorry. You're a Club 33 member. What is it like behind the doors?
Holly Madison
Really relaxing. It's so nice, especially when you have young kids, because they have a lounge in each park, so you can just kind of go there and get food and it's really chill. And if it's a hot day and you're tired of, like, being out among the crowds and they have nice bathrooms, so it's just a really chill escape.
Lauren Everts
And do they have a giant pickle behind there?
Holly Madison
I don't think they've ever offered that in the restaurants before. But you never know. The menu's always changing. They should offer the giant pickle.
Michael Bostic
Bring up the giant pickle. The last time we went, we had a. We had somebody that was guiding us around, and I was looking forward to that pickle. And I. Everyone had one. I looked over and the guide was eating my pickle. Just ate the whole thing.
Lauren Everts
He talks about this every day. It's traumatizing.
Holly Madison
Weird.
Michael Bostic
It was kind of weird.
Holly Madison
It's weird behavior for a guide. That is really strange.
Michael Bostic
Well, listen, I mean, I didn't want. I'm like, if you want a pickle, you're like, I'm gonna. But. But I didn't get one then, so I felt like it was.
Holly Madison
That's awful. Did you know if you're the first person on Main street to go and get the pickle, you get a special pin where it says first pickle of the day? I'm not a morning person, so I've never done it, but I am a pickle fan, so I'm kind of envious. I've never checked.
Lauren Everts
You need to do that, though, because you need to get the pin for your house. I feel like.
Holly Madison
Yeah, I think so.
Lauren Everts
You might need to do that one. Go get the giant pickle at Disneyland.
Michael Bostic
If you ever see me running through the park to get the pickle, something's gone really wrong in my life.
Lauren Everts
Well, I. I want to know what the requirements is. This is like a tangent to get in Club 33. Don't you, like, have to know someone who knows someone who knows someone? What's. What's the thing?
Holly Madison
Well, there's a really long waiting list. It does help if you have somebody who's already a member put in a good word for you. And I don't know what their criteria is, what they look for, when they. I'm sure they do background checks and everything. And you Just have to pay a big fee, and then you're in.
Lauren Everts
If they decide you, Michael, you better go rub elbows. It sounds like it's a nice place to bring the kids.
Michael Bostic
I'm gonna call Stamos up.
Lauren Everts
So while you're in college and going to Disneyland, at what point does everything happen with Playboy? Did you get approached? Did someone walk up to you? Was it something you sought out?
Holly Madison
Well, I was working for Hawaiian Tropic as well, and I was at one of the Hawaiian Tropic events, and Hugh Hefner's doctor came to that, and he said to the organizer, I want to invite all these girls to the next Playboy party. And I was really excited because back then, the Playboy parties were, like, the coolest parties in town. And I worked at the Hooters in Santa Monica that they used to have back then. It's closed now. And some of the girls there were, like, lucky enough to get to go. But it was, like, such a exclusive thing back then that I was so excited to go to the parties. And I was a fan of, you know, Playboy and, you know, some of the Playmates who were famous in the 90s. So I'd always wanted to be a part of the brand. So I was super excited to go. And then I got invited to, like, the pool parties, which were a lot smaller and more intimate. And I got to know Hef a little bit, just casually, but, you know, I kind of thought I knew him. And I was in a place in my life where I was trying to do too much. I was in college. I was trying to keep my grades up so I could keep my scholarships, but also work so I could pay my bills and also audition. And I was, like, doing so many things and kind of failing all of them. And it got to a point where I was living with a couple other people. They were telling me we weren't renewing the lease. At the last minute, my credit was in, how am I gonna get a place? I have nowhere to live? And some of the girls that were living with Hef had invited me out with him before, and I'd always said no, because that's obviously, like, an entryway into, like, this multiple girlfriend thing he had going on. But then when I had nowhere to live, I was kind of like, maybe I should give this a try. And it just turned into something that lasted way longer and was a way bigger thing in my life than I ever thought it would be.
Michael Bostic
So you were hesitant in the beginning?
Holly Madison
Oh, yeah. I had no interest. Like, I really liked Hef. I really thought he was cool and looked up to him and everything. And I love the. But I didn't want to be part of, like, a multiple girlfriend thing until I was desperate.
Lauren Everts
One thing I noticed about you from, as a viewer is that you like intellectual stimulation, and you seem like, this is so weird. And I don't know if this is true, but this is. Just seems like you're the only one out of all the people I saw around him that really liked his brain.
Holly Madison
Yeah, I think so. I mean, I can't speak for everybody else and say that wasn't attractive for them as well, but I definitely. That was a huge attraction. Like, I was so smart. Yeah. Turned on by, like, how much he knew and how much he'd accomplished and how capable he was and how creative he was. Like, those were all very attractive things to me, for sure.
Lauren Everts
So when does the show come around? How. How long have you been living there?
Holly Madison
I'd been living there about four years when the show came around, and it really changed everything. I was scared to do it at first. I had always wanted to be on camera as, like, a TV host or an actor, a model or something like that. I'd never wanted to be famous for my personal life, and I was in this situation that I was in it a hundred percent, but I was also kind of embarrassed about it, and there were a lot of things I hated about it, and I just didn't want to live that publicly. But I kind of felt like I had no choice but to do it unless I wanted to be kicked out on the street and start my life all over. So I thought, well, I'll give this a try. And I was very hesitant the first couple of seasons. I didn't really. I wasn't very open on camera. I didn't participate as much as the other girls, but I really got to a place where I felt like I could make the show work for me. And I felt like it brought me more opportunities and allowed me to be able to do more things in a situation that had a lot of restrictions on it. Like, Hef loved the show and how, you know, much it added to his life and how much it promoted his brand. So he was able to let me do more things than he would have done, let me do earlier in the relationship. So I saw that that worked for me, and I really got into that.
Lauren Everts
When you look back on the show. When I look back on the show, you were the star. At what point do you know you're.
Holly Madison
I didn't feel like I was that's what I was.
Lauren Everts
I kind of felt like at the time, you might not have known that, but, like, looking back when I was watching you were the star, what point did you realize you were the star?
Holly Madison
Oh, I never felt like I was on it at all.
Michael Bostic
Like, the entire time?
Holly Madison
No. Like, by far, like, Kendra was the most popular one at the time. Like, I never felt like I was. And I was always. Because of my relationship with Hef, he was a lot more protective of me and wouldn't let me do as much as the other girls. So as far as, like, ancillary things, like club appearances or going and doing a guest spot on this show or that show, I was allowed to do the least.
Michael Bostic
What do you mean by that? Like, from an outside perspective, you had to behave differently than the other two at the time, or you weren't allowed to do the same.
Lauren Everts
She was his main girlfriend. He seems like he's protective over you.
Holly Madison
Yeah, very possessive and wouldn't let me do different things. Like, I really wanted to do the first season of Celebrity Apprentice, and he wouldn't let me do that.
Michael Bostic
That would have been good.
Holly Madison
Yeah. Like, I couldn't go and do these outside things, so that sucked, but I didn't.
Michael Bostic
Was it just because he wanted you to Him?
Holly Madison
Yeah. He was very controlling and very possessive and didn't want me away from the house.
Michael Bostic
But the other two were allowed to.
Holly Madison
A little bit more. Yeah. I mean, they had strict rules and a curfew as well, but Bridget was allowed to do more than I was, and Kendra was allowed to do more than Bridget was, so.
Lauren Everts
So you. You don't think you're the star? I think you're the star of the show.
Holly Madison
Oh, thank you.
Lauren Everts
I mean, do you ever go back and watch or. No.
Holly Madison
Oh, yeah, we do. Cause Bridget and I do a Rewatch podcast, and we're about halfway through it, and it's just interesting to see, like, the whole evolution and how different, like, seasons one and two are from season three. And I'm so excited to get to the next. Cause I haven't seen anything from season five, the season when we left, since it first aired. So I'm excited to revisit that.
Lauren Everts
And when did you guys realize, like, you were onto something with the show? Like, when did you realize you couldn't go to lunch because people were coming up to you?
Holly Madison
That took a really long time because we lived in this bubble, and anytime we would go out with Hef, he attracted so much attention, and it was a long time before we were really allowed to do things on our own. And we would get that attention from the show. But it would take a couple seasons of the show being a hit before I felt like the general public really knew our names individually. So it wasn't really until season three that I started to feel like, oh, maybe we could get like a little extra opportunity here. Oh, people really know my name. Or, oh, I really can't go here. But I was living in so much of a bubble that I wasn't really going out by myself, doing things too much. It just kind of felt like the same fuss that had always happened around Hef was still happening. It's just now some of the people knew our names.
Lauren Everts
I think too, as a viewer, when I was watching, there was something like so sparkly and glamorous about it.
Holly Madison
Oh, I think that's what everybody loved about the show.
Lauren Everts
I don't know if it would work, like right now, today, but there was something about that. You were like, oh, my God, this is so amazing. They're letting you behind the gates. You guys are so beautiful. You're seeing inside your room. Like, it was very voyeuristic. I remember.
Holly Madison
Totally. A show like that would definitely not work today. Cause it was a show about a lifestyle. And you can see everybody's lifestyle on Instagram now, so. But this was before social media, so it was really intriguing. And everything on the show was colorful and oversaturated and costumes and outfits and parties and it was just like eye candy the whole time.
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Holly Madison
What.
Michael Bostic
Were the things that weren't glamorous behind the scenes that maybe weren't shown?
Holly Madison
Just all.
Lauren Everts
Let me pull out my scroll.
Holly Madison
Yeah. Well, the house wasn't always in the best shape. Like, I was always kind of lobbying, you know, half like, let's replace this carpet, or this isn't great, or. And he was very resistant to change and didn't want to spend the money on it. And then the company owned the house and didn't want to spend any money on anything. So there was a lot of stained carpet and a lot of, like, dogs peeing in the hallway and just things like that that weren't the best.
Lauren Everts
I think that if I was, like, evaluating him from a psych perspective, it's like he had this huge moment in the 60s or 70s or 80s. I don't know exactly what it was where he was like, the man. And then. So to change the house would have meant, like, he was moving on and evolving.
Holly Madison
Yeah.
Lauren Everts
Do you know what I'm saying? He was holding onto it.
Holly Madison
Yeah. He was really a creature of habit and loved routine and didn't like change. And I wasn't even necessarily trying to change, like, the 70s stuff because I thought that was kind of kitsch and fun and very, like, Playboy Mansion and kind of what people want to see a little bit. But just like, replace the carpet or, you know, just like, the cleanliness of it was more like what I was trying to get going.
Michael Bostic
Sounds a little musty.
Holly Madison
Yeah. I won A few battles. We got a lot of carpet taken out and a lot of, like, hardwood floor put in. So that was a start.
Lauren Everts
You. You made some moves, though, in that.
Holly Madison
I definitely.
Lauren Everts
Yeah, I feel like you made some moves. What point do you realize that you have your own personal brand outside of Playboy, outside of Hugh Hefner? Are you in the Mansion when you realize that, or did you have to remove yourself to figure that out?
Holly Madison
I definitely had to remove myself when I left the Mansion. I moved to Vegas and I had my own show on the Strip and I was doing my own spin off show. So that was kind of the start of it. But when you come from, like, the girls next door Playboy world, you can't ever really get out from under the Playboy umbrella ever. You know, it's always the thing that people want to talk about and stuff. And for a while, I didn't like that. And I really just thought, well, I'm never gonna be able to do anything else unless I just quit talking about it completely. But then I realized that that doesn't serve anybody. You know, it's part of my life, and I want to be able to claim the good parts of it too, as well as talk about the bad parts.
Michael Bostic
So is it mostly good memories? Because, you know, we've had different people that have had a similar experience to you in that place on the show, and it kind of varies person to person.
Lauren Everts
Yeah, it's funny, some people say they loved their.
Michael Bostic
Kendra was on and she looks fondly.
Lauren Everts
And then Crystal was on and she doesn't look fondly. It's like everyone has different perspective. It's interesting.
Holly Madison
It's so interesting because all the women who went through there had such different experiences, even as girlfriends. But you look at, like, playmates who came through. Like, if you were a playmate in the 90s. Like, Hef was married, he wasn't trying to sleep with anybody. This was like pre Viagra, you came and you stayed in the guest house and you shot your pictorial and you had a wonderful experience. So women who had that experience get really offended when I come out and tell my experience, because they want to come out and be like, well, no, my Playboy experience was great, and I'm sure it was, but that doesn't take away that mine wasn't. But to answer your question, I feel like, unfortunately, mine is a lot more bad memories. Especially when I think of the first four years I lived there. It was just a hellhole. It was like, none of the girls got along. It was super toxic. There was nothing fun about it, really. And then when the show came along, things changed and got a lot more positive. But what I like about doing the podcast with Bridget is it allows me to go back and, like, reclaim the good memories. Because I came out of the Mansion, I wrote my book, I talked about the side of living there that people didn't know and didn't get to see on tv. But now that I'm rewatching with Bridget, I can remember, oh, well, that girls trip was really fun. Or these movie nights were really nice. And it's nice to just have, like, a more holistic view now.
Lauren Everts
I feel it's probably therapeutic.
Holly Madison
100%.
Lauren Everts
Yeah. It's probably, like, good for your, like, inner child to go back and almost, like, reclaim the narrative of it. What was the final straw when you said you were done? You. Did you book your show before you. Did you book your show in Vegas before you left the Mansion?
Holly Madison
No, I had nothing. So it was, like, a big risk. Like, I didn't know. Like, obviously I was coming off of a hit, but I didn't know that I would land anywhere. Like, I hadn't been outside this bubble in so long, so I didn't have anything lined up waiting for me. But it. And it wasn't really one last straw thing. It was a couple things. One was I wanted to have kids, and that wasn't gonna happen. Two, Hef was changing a lot. I don't know what was going on with him. I don't know if it was, like, dementia kicking in or if it was other stress things I didn't know about, but he was getting really mean. Not that he'd never been mean to me before, but. But, you know, our relationship had gotten to a place where it had kind of evolved and gotten to a better place. And then all of a sudden, he's, like, snapping at me and yelling at me over weird things and, like, making. I was working at the Playboy studio at that time, you know, running all the Playmate pictorials, and he was starting to make that job impossible.
Lauren Everts
Well, you were getting independence.
Holly Madison
Yeah. And he probably felt it. Yeah. Yeah. So it was rough. It was. Those two things were the main things.
Michael Bostic
When you say, not that he'd never been mean to you before, what do you mean?
Holly Madison
Oh, I mean, he'd always had. There were always difficulties. You know, there was a really bad power imbalance in the relationship, and I was always very intimidated by him. So I put up with a lot of things, like him yelling, putting me down, pitting me against other girls, different things, like that and the relationship had its ups and downs and it had started to get better, you know, with the show and with less girlfriends. But then when things started to get bad again, I was like, I can't do this again. This is just too much.
Lauren Everts
I think there's like almost like a Stockholm element, like a Stockholm syndrome of living in that mansion. And then what she did, and you see it on the show is like she started to get independence and you started to become like, like an entrepreneur that I saw. And as she became the entrepreneur it. You probably needed him less. And so he probably was pissed. Amongst other things.
Holly Madison
Yeah, I think so. He saw a lot of my energy going toward my work at the studio. And it was weird because we made such a great team working together. Cause I would have to bring the product back to him at the end of the day in the photos and get his approval and, and you know, improve everything at the studio in ways that benefited him. But still it was just, it was rough.
Lauren Everts
When you got get to Vegas and you're away from the Playboy Mansion. Was it weird or liberating or everything?
Holly Madison
Everything. It was so strange. And it's so funny just seeing how warped my perspective was from living at the house. Because I was rewatching one of the first episodes of the spinoff I did after I had moved to Vegas and this outfit I'm wearing was so not anything anybody would wear in the real world. It was a jean skirt that was like so short you could see my underwear if I moved. And this tank top and like a bra underneath. Not even like a bralette or a cute bikini top, but a full on bra. And like the tank top is like pulled all the way down and stuff. And I think the fact that I lived in Vegas kind of like made it more okay than other places. And people weren't really like giving me weird looks or anything, but it was just like the amount of time it took for like what I thought was like appropriate and acceptable in the Playboy world to kind of wear off in the real world. There was definitely like a lag time. Like I look back on that, like who would go out in that? But it was just, I was still kind of in that mindset and it took like a couple years to kind of, you know, I think that's what.
Michael Bostic
You were wearing when I met you.
Lauren Everts
I was, I was inspired by the girls next door. I definitely took a lot of outfit inspiration from you guys. I think I used to go to Victoria's Secret and buy lingerie and then I would wear the lingerie. Out to the club all the time.
Holly Madison
Oh, my God. So that's.
Michael Bostic
You're like, who would do that?
Holly Madison
You're looking at her.
Lauren Everts
It was me.
Michael Bostic
It's her.
Holly Madison
It was me.
Lauren Everts
I used to be blonde too. I'll have to show my book. You can see I'm blonde over there. I used to be very blonde. I just. I love that era. It was like a special era.
Holly Madison
Yeah, for sure.
Lauren Everts
It was fun. You wore the show short skirts. My boobs were pushed up.
Holly Madison
Yeah.
Lauren Everts
There's been a lot of iterations of me, that's for sure. I keep it fun. What point do you get your show and what point does it blow up? Cause I remember there's billboards. It's all over Vegas. It was like the hot thing. When does that start to happen for you? From when the show stopped.
Holly Madison
It happened so quickly and I was so lucky. I mean, I was prepared for it too. Cause I was out there doing the meetings and the networking and trying to make it happen. But. But what happened was I was in talks a couple different places to do a burlesque show in Vegas. And I had gone through a bad breakup and I was kind of like at a friend's house, just feeling low and trying to manifest and everything. And I'd really wanted to do Dancing with the Stars for so long. Cause that show was so big back in the day. Like 28 million people would watch it. And anybody who wanted to relaunch their career or push something, that was the perfect platform to do it. And they never wanna be on the show. They're like, no, you dated an 80 year old man. Middle America's not gonna like you. Not gonna like pushing. Pushing. I want to do this. So somebody got injured before their eighth season started and they needed somebody last minute. And they're like, who would be desperate enough to come in with none of the training any of the other contestants have done? And they knew it would be me because I was bugging them so bad. So I got to do it. And it was so much fun. And I got the deal to be in my Vegas show when I was on Dancing with the Stars. So when I was eliminated from that show, I plugged it on tv and just every. The timing was so perfect and I couldn't have manifested it better.
Lauren Everts
When you blow up like that, is Hef, like trying to text you to come back or are you just ignoring him, blocking him?
Michael Bostic
Is he sending you emojis?
Holly Madison
Well, he definitely wasn't texting. He's more of a letter writer.
Lauren Everts
Oh, he's like carrier pigeon. Like, message in a bottle.
Michael Bostic
He's like, this will get to you in two weeks. Was it on that note?
Lauren Everts
A can with a string on it?
Michael Bostic
On that note, was it a challenge to date after leaving the mansion?
Holly Madison
I mean, there was a lot of people who wanted to date me, but I think in a very superficial way, I think it was like, oh, I want to date that hot girl on the billboard right there, and then tell my friends about it. But it's not really the type of, like, quality that I was looking for. As far as, like, a guy who wanted a relationship. I would say the most challenging thing is, like, people would get together with me, knowing exactly what my history was, and then they would all of a sudden have a problem with it. Like, after our relationship got serious, they'd get really, really jealous. They'd come up with all these imaginary scenarios in their heads about what could have possibly went on, and they're torturing me about it, and I'm like, bro, you knew you're not secure enough to handle this.
Michael Bostic
That's kind of what I meant. I didn't mean. I'm sure there was many suitors that were throwing their hat into the ring. It was more like, in that line, was it the relationships start to be a challenge?
Holly Madison
Yeah, I think so. But also, looking back, like, I didn't even know who I was at age 30. You know what I mean? I think you're really not gonna attract, like, the quality of relationship you want until you know who you are.
Michael Bostic
Like, what did you ask me the other day?
Lauren Everts
I'm just gonna say so. We were listening to Heather's podcast with you on it, and I heard you say that, like, the guy, like, they would date you knowing exactly who you were and exactly the history, and then they would get insecure and try to, like, dim your light. Yeah, I'm not saying it exact what you said, but I paused, and I said to Michael, I was like, would you care if I was a Playboy Playmate and I lived at the mansion? And you said, no, no, but Lauren.
Michael Bostic
Does these weird things.
Lauren Everts
She's like, what if one day I'm like, one whiteboarding? And I'm like, what if she loves to do these?
Michael Bostic
She's like, what if one day I grew flippers and a tail? Would you? And I'm like, why do you do.
Lauren Everts
These weird heads still like me?
Holly Madison
You have to say yes. If she says, would you still love me if I was a worm? I said, you can't say no.
Michael Bostic
Yeah, I don't think the Playboy stuff would rattle me too much. I, like, had to think about it. And then she's like, what about OnlyFans? I was like, well, what are you doing?
Lauren Everts
Oh, then I went to. Only I wanted to stretch it.
Holly Madison
And then she goes.
Michael Bostic
And I go, well, what are you doing on the OnlyFans?
Lauren Everts
Showing my butthole.
Michael Bostic
Well, then I was like, Then I need to, like, really understand, like, what's going on.
Lauren Everts
I don't like. But then I'm like, there's pre. Like, there's gonna be history that women have. All men have so much history. You guys, if someone gets mad about a woman's history, I would challenge them to pull out their history.
Michael Bostic
I would say the same thing about women with men.
Lauren Everts
Great.
Michael Bostic
Taylor, save this for me. Later, Taylor. Save it for later.
Lauren Everts
Let's pull out our producer Taylor's history.
Michael Bostic
Of course, we don't. We know that wasn't even part of the debate. We know where you stand.
Holly Madison
I wanna know what guys are in the Lily Phillips line.
Michael Bostic
So that's what I'm just kidding. No, but I was gonna say. Is that her? I was gonna ask. There's the OnlyFans person that's, like, sleeping with a lot of guys. And listen, no judgment. Do what you gotta do. Go with God. But.
Holly Madison
But the guy's in the line.
Lauren Everts
Yeah.
Michael Bostic
The guys in the. It kind of rattles me a bit. Yeah, that's more concerning.
Lauren Everts
Explain what exactly what it is like, she's having sex with a thousand men. Is that the one?
Holly Madison
Yeah. And all these guys line up and they have ski masks on to, like, partake.
Lauren Everts
Why ski masks? Cause they don't want people to see you there.
Holly Madison
Yeah, they wanna be anonymous, Taylor, for sure.
Lauren Everts
I just saw a ski mask in your briefcase. And by the. You a thousand percent.
Michael Bostic
What thousand million percent would do this?
Lauren Everts
Do they have a certain amount of time that they can have the sex when they're in. Like, when you get to the front of the line, like, is it like a ride? Like, you have a minute?
Holly Madison
I don't know. I've never heard them say. I don't know.
Lauren Everts
I think that that is part to me. I think the guy wants the story.
Holly Madison
Yeah, probably.
Michael Bostic
But like, that one, like, listen, it was like, hey, I did these things in the. No problem. But then, like, hey, one of the things I did was like, one day there was a thousand guys, I'd be like, whoa, I have to really think. I have to now think about that one a bit. I don't know how I'm bringing That home to mom. Let's just move on.
Lauren Everts
So when your show takes off and you're doing all these things, how did you continue to maintain the brand that you have? Because you've. I feel like you've. You're always relevant, you've always been really good with your brand. And it seems like you moved away from Playboy and did your own thing.
Holly Madison
Yeah, I really tried to, for sure. Yeah. I just kept it focused on what I was doing in Vegas and my show and being an entrepreneur and my friends on the show and what they were doing. I just really tried to focus on that. And sometimes on my show, like Playboy, storylines would come up because it was the same, you know, it was the same networks, it was the same kind of people who would work together and the same executive producer. But I tried to get away from it as much as possible.
Lauren Everts
And when did you write your book? In all of the.
Holly Madison
Not until 2015. So my TV shows were done. You know, I'd had my first child and just finally felt ready to talk about it because I'd been living this life where every day a stranger would come up to me and be like, how's Hef? Do you miss the mansion? Da da da. And I kind of felt compelled. Like, I felt like their expectation was they wanted to hear something positive because maybe they were a fan of the show, maybe they missed the show. And I would always say nice things. Cause I thought that was like the nice thing to do. But it just started to feel like living a lie after a minute and you just can't do it anymore. And I'm like, why am I kind of with this expectation to like keep up this myth of what the relationship was when it wasn't that and it wasn't something I would ever advise anybody else on getting into something similar.
Lauren Everts
Also, don't you think when you become a mother you just really start not to give a shit? Yeah, you just, there's something about it that you're just like, eh, like me, hate me. Like this is what I am. There's something that like happens totally where you're just, you're just kind of like done with the bullshit 100%. This episode is brought to you by Opill, the first over the counter daily birth control pill available in the US. Opill is a daily birth control pill that is FDA approved and full prescription strength. It's a progesterone only pill, meaning it does not contain estrogen. Progesterone only pills like opill have been FDA approved to prevent pregnancy for over 50 years. But now with opill, the way you are able to access daily birth control pills is completely in your hands. I know this would have been so amazing for me when I was in college to get access to birth control so easily. 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Holly Madison
I love it.
Lauren Everts
I know. It's like, I feel like it's such a fun chapter for you. What has that been like? It seems like you're very close with your daughter.
Holly Madison
Yeah, totally. Yeah. I just focus on trying to make the best memories I can for my kids and create those moments and, you know, come up with super fun things to do, things I would have loved to do at that age. And, you know, stay present, keep them off their iPad. So.
Lauren Everts
And when did you decide to do the Playboy show? That's the Rewatch show with Bridget. And why?
Holly Madison
Oh, we did that in. We started that two years ago. And I was on YouTube. I started YouTube during the pandemic, and people wanted me to react to episodes of Girls Next Door, so I did a couple of those. And as I watched them, I would think of so many things, and I would text Bridget, like, do you remember this? Do you remember what happened in this scene? What was going on in this scene? Oh, my God. I just remembered this. And this was so crazy. And I'm sending her, like, these psycho long voice notes. She was probably like, bitch, shut up. And I was like, this should just be a podcast, us going back and forth on this.
Lauren Everts
And has it been a hit with the fans?
Holly Madison
Yeah, 100%. And we're having so much fun with it.
Lauren Everts
And so then why add another podcast on top of this? Because they sent you something like, is this, like, another thing on top of what you're doing?
Holly Madison
Oh, the TV show. Yeah, yeah, yeah. I mean, I always wanted to go back to TV in some capacity, and to be offered a show that's one that I want would actually watch was so exciting to me. So I'm really happy to be doing that. It's our Third season of Playboy Murders. And then I have my second season of Lethally Blonde coming out after that, which is my other true crime show. That's not Playboy specific.
Lauren Everts
So you're busy. Yeah. As an entrepreneur, you're busy. What's a day in your life?
Holly Madison
Every day is very different. It kind of depends. I'm divorced, so I have joint custody. So if I'm with my kids, I try to do nothing else but be with my kids. Like, I'll fit stuff in when they're at school. Maybe I'll do like a podcast recording day when they're in school. And then days I don't have my kids, I'm usually just at home trying to get as much work done as possible, or I'm filming the show or I'm out doing press.
Lauren Everts
And what do you. What is your, like, vibe on social media? How do you show up on social media? Are you someone that checks in every day? Is it like, do you have, like, a content plan? What do you do there?
Holly Madison
I don't have a content plan. I used to back before I had as much stuff going on with the podcast and the TV shows. I have not been consistent. Consistent on TikTok regularly, or I'm more consistent on Instagram. I think I like to make reels about, like, places to go in Vegas and fun things to do in Vegas. I just like to share that for fun.
Lauren Everts
What's the best hotel in Vegas?
Holly Madison
I mean, I love Fontainebleau right now. Oh, Wynn was always my favorite up until then. But I love Fountain Blue.
Lauren Everts
Fountain Blue. And what's the best restaurant?
Holly Madison
Well, my favorite is Golden Steer. It's the oldest steakhouse in Vegas. It's been there so since the early 60s. And it's very old school and the food's amazing and I have my own.
Lauren Everts
Booth there, and that's really cool. We gotta go there.
Michael Bostic
Never been there.
Lauren Everts
I could. I just saying, after this pregnancy, I could use a pop puss Vegas trip. Yes, I'm ready to. I'm letting. I'm ready to let it rip.
Michael Bostic
I like going to Vegas. Don't twist that.
Lauren Everts
No, I think Vegas is really sexy with your husband. There's something about it that's really sexy. And, like, that is one thing I.
Michael Bostic
Miss about living in California is you can. You could go and you could jump on.
Lauren Everts
I mean, it's sexy without your husband too.
Michael Bostic
You could just jump on.
Lauren Everts
I like going with you. Like, I feel like it, like, makes us feel like we're like 20.
Michael Bostic
There you go. You get on the flight Go to dinner, stay out all night and go home. And you can be like literally, Taylor, remember when we did that? We got the room. We didn't even reuse the room. We just went out all night.
Lauren Everts
There's something so sexy about it.
Michael Bostic
We literally set our bags down and just ran around.
Holly Madison
That's so fun.
Lauren Everts
What can a guy do to impress you? We had Kimora on Kimora Lee Simmons yesterday and we asked her this and she had a video, a very specific list. What are, what's your list of what you're looking for?
Michael Bostic
She had a list that went out to the podcast.
Lauren Everts
Yeah, she had a big list.
Holly Madison
I just want like an amazing, good person who I'm attracted to. Like, I don't have any specific physical characteristics. Just I have to be attracted to him. So that kind of like is umbrella just covers it. I just have to be attracted to him. And I would like if he lives in Las Vegas, because I don't want to move.
Lauren Everts
Okay.
Holly Madison
He has to love it there as much as I do and he has to be like super motivated and successful to a point where like I can look up to him and be inspired by him.
Lauren Everts
That seems like an important one. I thought you were gonna say that. It seems like you need to be mentally stimulated.
Holly Madison
100%. Oh my God.
Lauren Everts
You're willing to move to Vegas.
Michael Bostic
You're gonna go to Vegas.
Holly Madison
I love Vegas.
Lauren Everts
He loves Vegas.
Michael Bostic
Stay behind the glass.
Lauren Everts
I'm telling you. What are some things that you do in your routine? Sorry, Michael, have to ask this for beauty, diet, fit, fitness.
Holly Madison
So many things. I don't know where to tell us.
Lauren Everts
This is the perfect podcast for you gotta tell us everything.
Holly Madison
Okay, where do I start? Okay, so in the morning I try and do like a quick workout. Like I have lists of like circuit training, strength training exercises I like to try and do. I have like one of those red light bed, sleeping bag things and like a red light mask. So I try to do that every day. I'm back on the green smoothie train. I just started doing that again. I do botox and facials regularly. What else? I know there's like 5 million things. Those are like the main things off the top of my head other than like going and getting my highlights done and stuff.
Lauren Everts
Any like specific wellness things? Do you cold plunge? Do you sauna?
Holly Madison
I love a sauna. When I have time, I sometimes I sneak into my ex husband's house and use his because I don't have one. I've only cold. I plunged once. It was super fun. But I Just never got around to it again.
Lauren Everts
Cold plunging is amazing.
Holly Madison
Yeah.
Lauren Everts
I miss it so much. Every single day I think about it. I'm not. I actually miss cold plunging more than I miss a margarita.
Michael Bostic
Really?
Lauren Everts
Yeah.
Holly Madison
Yeah. There's something fun about it. Like, it makes me so uncomfortable. I'm just, like, laughing the whole time.
Lauren Everts
Isn't it freezing in Alaska?
Holly Madison
It is, but you'd be so surprised how quickly your body forgets. Like, if I landed in Minnesota in the winter, I would be just as, like, freaked out as anybody else.
Lauren Everts
Like, I heard it's really good for your. Your skin and your body to be in cold weather. I heard that's how Russian women look so beautiful.
Holly Madison
Probably.
Lauren Everts
I'm. I hope I'm convincing you to move to Alaska.
Holly Madison
Russia.
Michael Bostic
Likely not.
Lauren Everts
But what's something that you're doing this year that's unapologetically for you?
Holly Madison
Damn. I don't know. I feel like I'm always doing stuff that's unapologetically for myself. Just if I'm not focused on my kids, I'm, like, carving out just whatever.
Lauren Everts
I can do, traveling. Are you, like, doing a lot of press? Are you out of Vegas a lot? What, like, what are the things that you do?
Holly Madison
I. Well, I think, honestly, like, one selfish thing is like, trying to be in Vegas more, because there's a lot of things trying to pull me other places, but I just like being home.
Lauren Everts
What's a rumor? This is from our team. What's a rumor or misconception that you would love to put to rest once?
Holly Madison
I don't know about putting anything to rest, but one of my favorite crazy rumors is, like, that I'm trans and not telling anybody.
Lauren Everts
You're not trans, I'm assuming.
Holly Madison
No. Cause I would tell everybody. But the funny thing was, was the person.
Lauren Everts
Where does anyone even get this?
Holly Madison
The person who came up with that rumor were, like, she has an Adam's apple, so she's trans. I'm like, this is just my neck. Like, this is just how it's always looked. But I think the funny thing is everybody's seen me totally naked to the vag from day one. So you'd think I'd have.
Lauren Everts
I'm Googling.
Holly Madison
So you think I'd have all those surgeries and not do the Adam's apple? Like, that would make no sense.
Lauren Everts
You guys. I hate to break it to anyone who thinks that in person, you're, like, the most feminine, petite. You remind me of, like, a fairy. There's no. Sorry to burst the Reddit thread. What Is bringing you the most joy right now?
Holly Madison
Just being with my kids and when I can, like, take things slow for a minute and just kind of relax.
Lauren Everts
It sounds like you're being present as a parent's really important deal.
Holly Madison
A hundred percent. Because, you know, being present for me is just a challenge. I'm always kind of thinking of the next thing and the next thing I want to do and the next idea and blah, blah, blah. So I try to car part. So I try to compartmentalize that to just when I'm not with my kids.
Lauren Everts
Who is Holly Madison? When the cameras are off, what is. What does it look like when you're just like eating popcorn, watching tv, relaxed.
Holly Madison
A slob, a sloth?
Lauren Everts
Are not full hair and makeup?
Holly Madison
No.
Lauren Everts
So what's your day when no one's looking, when you just can just be relaxed?
Holly Madison
I mean, if I had a day where I had nothing to do, I probably just wouldn't put on makeup. It would just be like, clean face, naked mole rat. I'm very naked mole rat vibes when I don't have the hair and makeup. Just hair pulled back in a ponytail, like ripped jeans, lounging around.
Lauren Everts
I'm laughing because we call our son the naked mole.
Holly Madison
Aw.
Lauren Everts
He actually has a naked mole stuffed animal.
Holly Madison
Aw, cute.
Michael Bostic
And then you'll see just like a naked body run across the house screaming, I have a naked mole.
Lauren Everts
Screaming penis. Okay, I wanna talk about what you're working on. So tell us first of all where we can watch it, what we can expect from this show. Tell us all the things.
Holly Madison
The Playboy Murder Season 3 premieres on Monday, May 5th. Then it'll be every Monday. There's. There's six new episodes this season. And I'm just really excited to share them. You know, all the episodes are so different. Some of the cases are unsolved. And that's always, you know, every true crime producer's dream is you hope that by sharing these stories, maybe some new leads will come up. And I really hope I'm sharing the victims stories in a way that's well rounded and represents them. And one thing I really love about this season is we had so many family members want to come forward and share their memories of their loved ones on the episode. When we first started doing the show, we would always reach out to the families and everything, but there were so few who wanted to participate. And I think now that we have a couple seasons out that people can binge and see how we handle the cases. People want to come forward and share more. And I like that. Because it's so unfortunate that the stories have to be shared, period. But if you're going to share these stories, like, I want the person to be as best represented as possible. And having their loved ones talk about who they are is so important, I think.
Lauren Everts
What's the case that that's really stood out to you?
Holly Madison
Well, the one we premiere with is about a woman named Kim Fattarini, and she was working for Playboy casting. She was found dead in 2017 of an apparent overdose. But there's a lot of things in this case that make people think it was not an overdose, that perhaps she was given ghb. And there's a current civil lawsuit pending, you know, from her parents, because it never evolved into a criminal case.
Lauren Everts
So did they find out who gave her the ghb?
Holly Madison
There's a suspect? Yes.
Lauren Everts
And is the sus. Is it open who the suspect is?
Holly Madison
Yeah, a football player named Sean Merriman. Allegedly Charger guy.
Lauren Everts
That's crazy. He used to be.
Michael Bostic
I used to see him in nightclubs all the time back then.
Lauren Everts
Nightclubs in San Diego.
Michael Bostic
That's.
Lauren Everts
I remember seeing him at, like, Flux.
Michael Bostic
He's a big dude, so.
Lauren Everts
So there's been no, like, no one said, this is who it is. It's still. It's just a suspect.
Holly Madison
I mean, his name has been brought up. Yeah, he's named in the civil trial that's pending.
Lauren Everts
Do you think through this show that you guys will be able to maybe get some closure in certain areas that would not have been able to get closure if the show didn't exist?
Holly Madison
I hope so. I mean, that's all we can hope for, covering these stories.
Lauren Everts
I mean, it sounds like that's, like, very cool, and it sounds like that's very. Feels purposeful to you to be able to do this.
Holly Madison
It definitely feels purposeful. And my other show, Lethally Blonde, which isn't Playboy centric, we cover a lot of stories, not all of them, but a lot of stories that involve sex workers. And I really love to try and get into who they were and talk about who they were besides just being a sex worker. Because women just tend to be written off as that and like, as that's the only thing they are. Especially, you know, in crime. Unfortunately, perpetrators oftentimes look for sex workers because they think that they're these off the grid people that have no family or aren't gonna have anybody looking for them. So they think it's gonna be something they can get away with. So I really like to go into those stories and Try and find out more about this human being and who was she and what was going on in her life and what was she missing out on from being stolen too soon?
Lauren Everts
I'm sure the families are so thankful.
Holly Madison
I hope so. I mean, it's hard either way, I'm sure, to have these cases brought out. It's such an emotional thing. But I hope that, you know, some positive can from it. For sure.
Lauren Everts
It's really cool what you're doing. I love this.
Holly Madison
Thank you.
Lauren Everts
I do think you should write another book. I'm just putting it out there.
Holly Madison
Yeah. I wonder what the twist would be or what the topic would be.
Lauren Everts
I think it's just like you've had this full life post your last book, and it's interesting. I know you wrote about your. I know you wrote about your show in your last book, but I think it would be cool to just talk about everything that you're doing now.
Holly Madison
Yeah, that'd be fun. Maybe in a couple years.
Lauren Everts
Yeah. Holly Madison, where can we watch your show, listen to your podcast, follow you, buy your book? Her book is really good, you guys. I didn't put it down.
Holly Madison
Thank you. Well, my new show, like I said, it premieres May 5th on Investigation Discovery. It'll be streaming on Max. And the first two seasons of Playboy Murders and the first season of Lethally Blonde are currently streaming on Max. My Instagram is Holly Madison. I have all my links in the bio for where you can buy my book and where you can see my podcast, Girls Next Level drops every Monday.
Lauren Everts
Thank you for coming on the show.
Holly Madison
Thank you. Thank you for having me.
The Skinny Confidential Him & Her Podcast: Holly Madison On Life At The Playboy Mansion, Early 2000’s Fame, & Finding Herself Again
Release Date: June 12, 2025
Hosts: Lauryn Bosstick & Michael Bosstick
Guest: Holly Madison
Production: Dear Media
In this engaging episode of The Skinny Confidential Him & Her Podcast, hosts Lauren Bosstick and Michael Bosstick welcome Holly Madison, renowned for her time at the Playboy Mansion, her reality TV presence, and her entrepreneurial ventures. Lauryn introduces Holly by highlighting her books—Down the Rabbit Hole and The Vegas Diaries—and her appearances on Girls Next Door and her own reality show, Holly's World.
Holly Madison opens up about her imaginative childhood in the remote landscapes of Alaska, where she spent much of her time playing in the woods. Despite living almost off the grid, Holly developed a keen interest in old Hollywood and unsolved mysteries from a young age. She recounts, “One of my earliest special interests as a kid was old Hollywood... I was really into the Little House on the Prairie books” ([04:00]).
Holly describes her move to Los Angeles, driven by a fascination with old Hollywood glamour and the boundless opportunities the city offered. She attended Loyola Marymount University to immerse herself in the LA scene. Her entry into the Playboy world was somewhat serendipitous—being invited to Playboy parties through her work with Hawaiian Tropic and Hooters in Santa Monica. Reflecting on her relationship with Hugh Hefner, Holly shares, “I thought I knew him... It was something that lasted way longer and was way bigger than I ever thought it would be” ([11:59]).
Holly discusses her four-year tenure at the Playboy Mansion, emphasizing the initial toxicity and power dynamics within the house. She reveals, “None of the girls got along. It was super toxic” ([24:07]). The advent of the reality show Girls Next Door marked a turning point, altering her public perception and providing new opportunities despite Hef’s controlling nature. Holly notes, “I really got to a place where I felt like I could make the show work for me” ([13:45]).
Note: This segment of the transcript includes advertisements and non-content sections, which have been excluded from the summary as per instructions.
After leaving the Mansion, Holly experienced a mix of liberation and challenges. She recounts, “It was so strange... the amount of time it took for like what I thought was like appropriate and acceptable in the Playboy world to kind of wear off in the real world” ([28:44]). Transitioning to Las Vegas, she launched her own show and began to establish an independent brand separate from Playboy. Holly emphasizes the importance of reclaiming her narrative, stating, “Now that I'm rewatching with Bridget, I can remember... just have a more holistic view now” ([25:15]).
Holly also speaks about her ventures into true crime with Playboy Murders and Lethally Blonde, aiming to shed light on complex human stories and provide closure for affected families. She mentions, “I feel like my other show, Lethally Blonde, which isn't Playboy-centric, we cover a lot of stories... who was she and what was going on in her life” ([54:35]).
Becoming a mother marked a significant shift in Holly’s priorities. She shares the joy and fulfillment of raising her daughter, focusing on creating meaningful memories and being present. “I just focus on trying to make the best memories I can for my kids and create those moments” ([42:48]). Motherhood also catalyzed her personal growth, helping her to establish boundaries and prioritize her well-being over public perception.
Holly details her comprehensive wellness routine, which includes daily workouts, scalp massages, microneedling, and regular botox and facials. She emphasizes the importance of a balanced lifestyle: “In the morning I try and do like a quick workout... I was back on the green smoothie train” ([47:16]). Additionally, she enjoys saunas and occasionally resorts to her ex-husband’s facilities to maintain her wellness practices.
Holly previews her upcoming third season of Playboy Murders, set to premiere on May 5th on Investigation Discovery and stream on Max. She highlights the season’s focus on unsolved cases and the involvement of family members for a more comprehensive storytelling approach. Holly expresses hope that the show will provide closure for some victims’ families: “I hope so. That's all we can hope for, covering these stories” ([53:44]).
She also discusses her successful podcast, Girls Next Level, where she and Bridget Bryant rewatch and dissect episodes of Girls Next Door, offering new insights and preserving both the good and challenging memories. Holly encourages listeners to follow her on Instagram and tune into her shows for more content.
Holly Madison ([03:43]): "I'm very curious. I'm all over the place. Anything from, like, health and wellness to unsolved mysteries to, you know, history."
Holly Madison ([11:59]): "I kind of thought I knew him. And I was in a place in my life where I was trying to do too much... It was just something that lasted way longer and was way bigger than I ever thought it would be."
Holly Madison ([24:07]): "None of the girls got along. It was super toxic."
Holly Madison ([25:15]): "It's probably therapeutic. 100%."
Holly Madison ([53:44]): "It definitely feels purposeful."
This episode offers a candid and comprehensive look into Holly Madison’s multifaceted life—from her early interests and challenging years at the Playboy Mansion to her successful transition into motherhood and entrepreneurship. Holly’s journey underscores themes of personal growth, resilience, and the power of reclaiming one’s narrative. Listeners gain valuable insights into navigating fame, building a personal brand, and finding joy in new chapters of life.
Where to Follow Holly Madison:
Tune in next week for another insightful episode of The Skinny Confidential Him & Her Podcast.