The Skinny Confidential Him & Her Podcast - Holly Madison On Life At The Playboy Mansion, Early 2000’s Fame, & Finding Herself Again

Episode Date: June 12, 2025

#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. In this episode, Holly opens up about her experience living in the Mansion, the pivotal moments in her upbringing that shaped her path, & the untold stories behind the gates of Playboy! She dives into iconic pop culture moments from the early 2000s, her evolution into a true crime host on The Playboy Murders with Investigation Discovery, & the success of her podcast Girls Next Level – where she & co-host Bridget Marquardt revisit the legendary series & share what really happened off camera.   To Watch the Show click HERE   For Detailed Show Notes visit TSCPODCAST.COM   To connect with Holly Madison click HERE   To connect with Lauryn Bosstick click HERE   To connect with Michael Bosstick click HERE   Read More on The Skinny Confidential HERE   Head to our ShopMy page HERE and LTK page HERE to find all of the products mentioned in each episode.   Get your burning questions featured on the show! Leave the Him & Her Show a voicemail at [phone].   This episode is sponsored by BUMPSUIT To Shop the Lauryn Bosstick x Bumpsuit Collection visit https://bit.ly/BUMPSUITXLB and use code SKINNY for 15% off for a limited time.    This episode is sponsored by Active Skin Repair Visit https://ActiveSkinRepair.com to learn more about Active Skin Repair and to get 20% off your order, use code SKINNY. This episode is sponsored by Nutrafol For a limited time, Nutrafol is offering our listeners $10 off your first month’s subscription and free shipping when you go to http://Nutrafol.com and enter the promo code SKINNYHAIR.   This episode is sponsored by Simply Pop  Sip on the juicy side of life. Find out where you can try Simply Pop at http://cokeurl.com/simplyPOP!   This episode is sponsored by Opill Opill is birth control in your control, and you can use code SKINNY for 25% off your first month of Opill at http://Opill.com.    This episode is sponsored by Spritz Society Spritz Society is now available everywhere! Head to http://spritzsociety.com to find a store near you, and make sure to follow @spritz on Instagram for all their latest announcements and upcoming events. Spritz Society, Summer Starts Here!   This episode is sponsored by Boulevard Boulevard is offering new customers 10% off your first year subscription when you go to join http://BLVD.com/SKINNY and book a demo.   Produced by Dear Media

The following podcast is a Dear Media production. He and her. Ah-ha! 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. 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 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. This is the skinny confidential, Him and Her. Taylor, are you excited for this episode?

Don't get too excited. Stay behind the glass back there. I'm worried. Holly Madison, why true crime? 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 like stay up late and watch it. I've always loved kind of

like spooky unsolved things like that. I've always been intrigued by it. Even one of my earliest special interests as a kid was like old Hollywood, but I was always really attracted to the stories 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 want 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. So there's a thread with Playboy playmates who have been killed.

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. One thing about you that I think is really cool, I told you off air, I've seen all your shows, your books, your podcasts, every time you off air, I've seen all your shows, your books, your podcasts, every time you're on Heather McDonald's, is that you have a lot of different interests.

Yeah. Like you seem like a curious person. I'm very curious, yeah, I'm all over the place. Anything from like health and wellness, to unsolved mysteries, to history. I love like niche history topics. Have you been like that since you were little? What were you like as a little girl?

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, yeah, that's where I grew up. 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 and 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. What did your family do in Alaska? My dad worked in the timber industry. He was a port manager. You know what?

I actually am not surprised that you grew up in Alaska. Really? Because your skin looks so good. Thank you. So does yours. 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. Thank you so much. And it's probably because it gets dark earlier there. 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 you know, 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

because I had acne and then like not seeing the sun throughout my childhood, I think that helped a lot too. I mean, maybe we need to move to Alaska because it really is. We'll just do like a big, dear media Alaska. Yes. 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 it? 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 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. Definitely, definitely did that. Definitely 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?

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. 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? I don't know, he's pretty up there.

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. So when you move down here, you're in college. Yeah. What do you mean Disney fan? Like you're like hanging out there all the time or you're just sort of like really into the Disney lore? 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.

I bet there's your trip good to trivia with it too. I think so, yeah. I'm getting back into it now that we have young kids. One time I tried it. I hadn't, 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. You tried to finger me in Disneyland in sixth grade

I still might try you you tried to finger me in sixth grade at Disneyland No, but then I just went this last time as an adult and I stood around him I think it's kind of weird that I'm just standing here as a grown man I had a corndog and I left well You know what's weird about it now is it's so crowded all the time. Yeah, it's a lot It's really 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 parts yourself. No lines on anything nobody there

There's no such thing as a not busy day have the park to yourself, no lines on anything, nobody there. There's no such thing as a not busy day. Will you go to Disneyland without getting like the plaid person? 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 just keep it low key. Hold on. You're a club 55 member. Club 33, yeah. 55's in the south of France. Sorry. You're a club 33 member? Club 33, yeah. The club is in the south of France! Sorry. You're a club 33 member. What is it like behind the doors? 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 being out among the crowds and they have nice bathrooms so it's just a really chill escape and do they have a giant pickle behind there? I don't think they've ever offered that in the restaurants before but you know the menus always changing Bring up the giant pickle the last time we went we had a we had somebody that was guiding us around

I was looking forward to that pickle and I everyone had when I looked over and the guide was eating my pickle just Every day and everyone had one, I looked over and the guide was eating my pickle. Just ate the whole thing. He talks about this every day. Traumatizing. That is weird. That's weird behavior for a guide. That is really strange. Well, listen, I mean, I didn't want it. I'm like, if you want a pickle, you're going to like, I'm going to, but I didn't get one then so I felt like it was.

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 that off my list. You need to do that though, cause you need to get the pin for your house. I feel like.

Yeah, I think so. You might need to do that once. Go get the giant pickle at Disneyland. Have you ever seen me running through the park to get the pickle? Something's gone really wrong in my life. Well, 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 the thing? 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 just have to pay a big

fee and then you're in if they decide. Michael, you better go rub elbows. It sounds like it's a nice place to bring the kids. and everything and you just have to pay a big fee and then you're in if they decide you're in. Michael, you better go rub elbows. It sounds like it's a nice place to bring the kids. I'm gonna call Stamos up. 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? 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 an exclusive thing back then that I was so excited to go to the parties. And I was a fan of Playboy and some of the Playmates who are 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 the pool parties, which were a lot smaller and more intimate.

And I got to know Hef a little bit just casually. But 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 the toilet

How am I gonna get a place? I've 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 entry way 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.

So you were hesitant at the beginning. Oh yeah, I had no interest. Like I really liked Teff. I really thought he was cool and looked up to him and everything. And I loved the brand, but I didn't want to be part of like a multiple girlfriend thing until I was desperate.

One thing I noticed about you as a viewer is that you like intellectual stimulation and you seem like this is so weird and I don't know if it's 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. 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 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. So when does the show come around? How long have you been living there? 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 cameras like a TV host or an actor or a model or something like that. I 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, Heff 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.

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 the star? Oh thanks, I didn't feel like I was. I kind of felt like you 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? Oh, I never felt like I was on it at all. The entire time? No, like by far like Kendra was the most popular one at the time. Like I never felt like I was on it at all. Like, I was... The entire time? 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 Heffie, 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. What do you mean by that? Like, is 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 thing? She was his main girlfriend. He seems like he's protective over you. 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.

That would've been good. Yeah, like, I couldn't go and do these outside things. So that sucked. But I did have. It was just because he wanted you to him, to him? Like you were. Yeah. He was very controlling and very possessive and didn't want me away from the house.

But the other two were allowed to. 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. So you don't think you're the star? I think you're the star of the show. Oh, thank you.

I mean, do you ever go back and watch or no? Oh yeah, we do, because Bridget and I do a re-watch 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 seasons, because I haven't seen anything from season five, the season when we left since it first aired. So I'm excited to revisit that.

When did you guys realize like you were on to something with the show? Like when did you realize you couldn't go to lunch because people were coming up to you? That took a really long time because we lived in this bubble. And anytime we would go out with half 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 Heff was still happening. It's just now some of the people knew our names. I think too, as a viewer, when I was watching watching there was something like so sparkly and glamorous about it. Oh, I think that's what everybody loved about the show.

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 like, you're seeing inside your room. Like it was very voyeuristic, I remember. Totally, a show like that would definitely not work today because it was a show about a lifestyle and you can see everybody's lifestyle on Instagram now. But this was before social media. So it was really intriguing and everything on the show

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to find where you can try Simply Pop. Find Simply Pop in any of its five juicy flavors by visiting them online at cokeurl.com slash Simply Pop. That's cokeurl.com slash Simply Pop. What were the things that weren't glamorous behind the scenes that maybe weren't shown? Just all, let me pull out my scroll. 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. 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 but

Weren't the best 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. Yeah I think so. Do you know what I'm saying? Like he was like holding on to it. 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. Sounds a little musty. Yeah. I want 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. You made some moves though in there.

I definitely. 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 realized that or did you have to remove yourself to figure that out? 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 spinoff 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 Play 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 going to 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 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, 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.

Yeah, it's funny. Some people say they loved it. Kendra was on and she looks fondly. And then Crystal was on and she doesn't look fondly. It's like everyone has different perspective. It's interesting. 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 Heff was married. He wasn't trying to sleep with anybody. This was like pre-Vaegra. You know, 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 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 girl's trip was really fun or these movie nights were really nice and it's nice to just have like a more holistic

View now I feel it's probably therapeutic hundred percent 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? Did you book your show before you, did you book your show in Vegas before you left the mansion? 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 show 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 was, 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 you you know, our relationship had got 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. Well, you were getting independence. Yeah. Yeah. So it was rough. It was those two things were the main things. When you say not that he'd never been mean to you before, what do you mean? 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. I think there's like almost like a Stockholm element, like a Stockholm syndrome of living in that 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 an entrepreneur, that I saw. And as she became the entrepreneur, you probably needed him less. And so he probably was pissed, amongst other things. 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, because I would have to bring the product back to him at the end of the day in the photos and get his approval and improve everything at the studio in ways that benefited him. But still, it was just rough. When you get to Vegas and you're away from the Playboy mansion, was it weird or liberating or everything? 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 spin-off 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 and 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 of years to kind of, you know. Calibrate. I think that's what you were wearing when I met you, Lola. 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. Oh my God. So that's, you're like, who would do that? You're looking at her. Me. It's her. It was her. It was me.

I used to be blonde too. We'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, it's a special era. It was a fun era, yeah, for sure. It was fun.

You could, like, you wore like the short skirts. Oh, I remember. My boobs were pushed up. I remember. Yeah, 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?

Because I remember there's billboards. It's like all over Vegas. It was like the hot thing. When does that start to happen for you from when the show stopped? It happened so quickly and I was so lucky. I mean, I was prepared for it too, because I was out there doing the meetings

and the networking and trying to make it happen. 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, because that show was so big back in the day.

Like, 28 million people would watch it, and anybody who wanted to, like, relaunch their career or push something, that was, like, the perfect platform to do it. And they never want to be on the show. They're like, no, you dated an 80-year-old man. Middle America's not gonna like you, not gonna do it. But I kept, 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 could plugged it on TV and just every, the timing was so perfect and I couldn't have manifested it better.

When you blow up like that, is Hef like trying to text you to come back or are you just ignoring him blocking your phone? Was he sending you emojis? We definitely wasn't texting. He's more of a letter writer. Oh, he's like carrier pigeon. Yeah. Message in a bottle. He's like, this will get to you in two weeks.

Was it on that note? A can with a string on it. On that note, was it a challenge to date after leaving the mansion? 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're not secure enough to handle this. 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? 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 the quality of relationship you want until you know who you are. What did you ask me the other day? I'm just gonna say, so we were listening to Heather's podcast, If You Want 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, 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 like, I lived at the mansion and you said no. No, but Lauren does these weird things. She's like, what if one day- I know, I'm like whiteboarding and I'm like, what if?

She loves to do this, she's like, what if one day I grew flippers and a tail'm like whiteboarding and I'm like, what if? She loves to do these, she's like, what if one day I grew flippers and a tail? And I'm like, why do you do these weird hypotheticals? But do you still like me? You have to say yes if she says what you saw me if I was a worm. I said... First, you can't say no. 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? Oh, then I went to Only, I wanted to stretch it. Then I go, well, what are you doing on the OnlyFans? Showing my butt hole.. And then she was like, what about OnlyFans? I was like, well, what are you doing? Oh, then I went to Only. I wanted to stretch it. Then she goes, then I go, well, what are you doing on the OnlyFans? Showing my butt hole. Well, then I was like, then I need to really understand what's going on.

I don't, like, there's pre-, like, there's gonna be history that women have. All men have so much history. But like, what's that? You guys, if someone gets mad about a woman's history, I would challenge them to pull out their history. I would say the same thing with women with men. Yeah, great. Let's pull out the box.

Taylor, save this for me later. Taylor, save it for her. Like, let's pull out our producer Taylor's history. Of course. We know. That wasn't even part of the debate. We know where you stand. I want to know what guys are in the Lily Phillips line.

Just kidding. No, but I was going to say, I was going to ask, there's the OnlyFans person that's like sleeping with a lot of guys and listen, no judgment. Do what you got to do. Go with God. But the guys in the line. Yeah, the guys in the line. It kind of rattles me a bit. Yeah, that's more concerning. Explain what exactly what it is.

She's having sex with a thousand men. Is that the one? Yeah, and all these guys line up and they have ski masks on to like partake. Why ski masks? Cause they don't want people to see you there. Yeah, they want to be anonymous. Taylor, for sure.

I just saw a ski mask in your briefcase. And you buy the, you are 1000% what? 1000 million percent would do this. 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.

I don't know. I've never heard them say, I don't know. I think that that is part to me, I think the guy wants the story. Yeah, probably. 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. It'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. So when your show takes off and you're doing all these things, how did you continue to maintain the brand that you have?

Cause 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. 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 producer But I tried to get away from it as much as possible. And when did you write your book in all of this? 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 for every day. A stranger would come up to me and be like, How's Heft? You missed 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, because 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 saddled 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 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 Like me hate me. I know this is what I am. Yeah, there's something that like happens Totally you're just you're just kind of like done with the bullshit. 100%. This episode is brought to you by O-PIL, the first over-the-counter daily birth control pill available in the US.

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I know it's like, I feel like it's such a fun chapter for you. What is that Ben like? It seems like you're very close with your daughter. 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 iPads. So, and when did you decide to do the Playboy show that's the rewatch show with Bridget? And why? 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. And has it been a hit with the fans? Yeah 100% and we're having so much fun with it. 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?

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 would actually watch. It 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 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. So you're busy. Yeah. As an entrepreneur, you're busy. For sure. What's the day in your life?

Every day is very different. It kinda 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.

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? 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 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.

What's the best hotel in Vegas? I mean, I love Fountain Blue right now. Oh, we gotta go there. Wynn was always my favorite up until then, but I love Fountain Blue. Fountain Blue, and what's the best restaurant? Well, my favorite is Golden Steer. It's the oldest steakhouse in Vegas.

It's been there since the early 60s, and it's very old school and the food's amazing, and I have my own booth there. That's really cool. we gotta go there. Never been there. I'm just saying after this pregnancy, I could use a pop-puss Vegas trip. Yes.

I'm ready to let it rip. I like going to Vegas, don't have to twist my arm. I think Vegas is really sexy with your husband. There's something about it that's really sexy and hot. That is one thing I miss about living in California is you could go And you could jump on I mean it's sexy without your husband Like I like going with you like I feel like it's like makes us feel like we're like 20 there you go you get on the flight good dinner stay out all night go home

You can be like little Taylor. We did that we got the room. We didn't even we use the room We just went out. Oh, it's there's something so sexy about it. We literally set our bags down and just ran around What can a guy do to impress you? We had we had Kimora on Kimora Lee Simmons yesterday and we asked her this and she had a very specific list What are what's your list of what you're looking for? She had a list that went out to the List I just want like an amazing good person who I'm attracted to. I don't have any specific physical characteristics, just I have to be attracted to him. So that kind of like his 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. 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. That seems like an important one. I knew I thought you were going to say that. It seems like you need to be mentally stimulated. 100 percent. Oh my god. You're willing to move to Vegas? So you're going to go to Vegas? I love Vegas. He loves Vegas. Stay behind the glass. I'm telling you.

What are some things that you do in your routine? Sorry, Michael, I have to ask this for beauty diet fitness. So many things. I don't know where to start. Tell us, this is the perfect podcast for you. You got to tell us everything.

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 five 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 like that. Any like specific wellness things? Do you cold plunge? Do you sauna? I love a sauna when I have time.

Sometimes I sneak into my ex-husband's house and use his, cause I don't have one. I've only cold plunged once. It was super fun. I just never got around to it again. Cold plunging is amazing. Yeah. I miss it so much. Every single day I think about it.

I'm not, I actually miss cold plunging more than I miss Margarita. Really? Yeah. Yeah, there's something fun about it. Like it makes me so uncomfortable. I'm just like laughing the whole time. Isn't it freezing in Alaska? 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. I heard it's really good for your skin and your body to be in cold weather. I heard that's how Russian women look so beautiful. Probably, yeah. I hope I'm convincing you to move to Alaska. Alaska or Russia.

Likely not, but... What's something that you're doing this year that's unapologetically for you? 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 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? 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. What's a rumor? This is this is a from our team. What's a rumor or misconception that you would love to put to rest once and for all?

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 You're not trans. I'm because I would tell everybody but the funny thing was 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 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, is like, everybody's seen me totally naked to the vag from day one. So you'd think I'd have-

Taylor's googling it. So you'd think I'd have all those surgeries and not do the Adam's apple. Like, that would make no sense. 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. Yeah, thanks.

There's no, sorry to burst the Reddit thread. What is bringing you the most joy right now? Just being with my kids and when I can like take things slow for a minute and just kind of relax. It sounds like you're, being present as a parent is really important to you. 100% 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 compartmentalize that to just when I'm not with my kids.

Who is Holly Madison when the cameras are off? What does it look like when you're just like eating popcorn watching TV relaxed? A sloth. A sloth. Yeah. Are you not full hair and makeup? What does it look like when you're just like eating popcorn, watching TV, relaxed? A sloth. A sloth. Yeah. Are you not full hair and makeup? No.

So what's your like day when no one's looking, when you just can just be relaxed? 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 like the hair and makeup. Just hair pulled back in a ponytail, like ripped jeans lounging around.

I'm laughing because we call our son the naked mole. Aw. He actually has a naked mole stuffed animal. Aw, cute. And you'll see just like a naked body run across the house. That is so funny. Screaming penis. Okay, I want to talk about what you're working on.

So tell us where we, first of all, where we can watch it, what we can expect from the show. Tell us all the things. The Playboy Murders season three premieres on Monday, May 5th, and it'll be every Monday. 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 as you hope that by sharing these stories

maybe some new leads will come up. And I really hope I'm sharing the victim's 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 gonna 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. What's the case that's really stood out to you? Well the one we premier 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. So did they find out who gave her the GHB? There's a suspect, yes. And is it open who the suspect is? Yeah, a football player named Sean Merryman, allegedly. Charger guy. That's crazy. He used to be- I used to see him at nightclubs all the time back in the day.

He used to be at nightclubs in San Diego. I remember seeing him at Flux. He's a big dude. So there's been no, like, no one said this is who it is. It's still, it's just a suspect. I mean, his name has been brought up. Yeah, he's named in the civil trial that's pending. 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? I hope so. I mean, that's all we can hope for covering these stories. I mean, it sounds like that's very cool and it sounds like that feels purposeful to you to be able to do this. 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 going to

have anybody looking for them. So they think it's going to 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. I'm sure the families are so thankful. 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, some positive can come from it for sure. It's really cool way, I'm sure, to have these cases brought out. It's such an emotional thing, but I hope that some positive can come from it for sure. It's really cool what you're doing. I love this. Thank you. I do think you should write another book. I'm just putting it out there. Yeah, I wonder what the twist would be

or what the topic would be. 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 show in your last book but I think it would be cool to just talk about everything that you're doing now. Yeah, that'd be fun. Maybe in a couple years. 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. 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 Thank you for coming on the show. Thank you. Thank you having me