Holly Madison: Hugh Hefner offered me $3 million (in his will) to stay with him


Here is the cover of Holly Madison’s new memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny. This isn’t a cutesy tail (get it?) of fun Playboy mansion adventures though. Holly gets surprising dark about her time as one of Hugh Hefner’s “girlfriends,” including some pretty candid revelations about suicidal thoughts, drugs, body image and money. Oh, and she says she never signed a nondisclosure agreement, so I guess she doesn’t have to worry about getting sued? Sure. We’ll see. Some highlights (the book is being excerpted all over the place):

The first time she met Hef in 2001: “‘Would you like a Quaalude?’ Hef asked, leaning toward me with a bunch of large horse pills in his hands, held together by a crumpled tissue,” Madison wrote in her memoir. After she declined the drugs, “Hef did not miss a beat: ‘Okay, that’s good,’ he said, nonchalantly. ‘Usually, I don’t approve of drugs, but you know, in the ‘70s they used to call these pills thigh openers.’ I want to scream ‘PAUSE!’ and freeze-frame that moment of my life. I want to grab that young girl, shake her back into reality and scream, ‘What the hell are you thinking?’”

Becoming one of Hef’s girlfriends: “I learned Hef was the manipulator and that he pitted us against one another. I realized I wasn’t treated well. I’m done being afraid of people. I don’t have any loyalty to Hef. I haven’t talked to him in four years, so there’s no reason to reach out now. Besides, it’s the truth.”

When she wanted to leave, Hef tried to get her to stay by putting her in his will: “It was there, in black and white. The will stated that $3,000,000 would be bestowed to Holly Madison at the time of his death (provided I still lived in the Mansion). At the time, it was more money than I’d ever know what to do with… But I didn’t want it. I actually pitied him for stooping to that level. I couldn’t help but be offended. Did he really think he could buy me? I put the folder back on the bed just as I had found it and never breathed a word of it.”

She thought about suicide in 2002: Her “misery” became so all-encompassing that in the tell-all, Madison, 35, recalls lying in a bath in 2002 and pondering: “If I just put my head under water and take a deep breath in, it would all be over…Would anyone even miss me?” She tells how the “depths of my own depression” had led her down a dark path and there was no light at the end of the tunnel. “Maybe it was the pot and the alcohol, but drowning myself seemed like the logical way to escape the ridiculous life I was leading.”

Life at the mansion: “Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in.”

She and Hef discussed having a child together: “I know how absolutely insane it sounds to want to have kids with someone in their 70s. You are basically robbing a child of his or her father before it is even born. Now that I am a mom myself, the idea seems even more unpalatable. But I suppose I thought of it as a ticket out – in more ways than one. The last time the mansion had been multiple-girlfriend-free was when Hef was married and had two children.” She reveals that Hefner had even submitted semen samples to a fertility doctor – only to discover that nothing was viable. “This was concrete proof slapping me in the face that there was no future for me at the mansion and it was either sit in there and rot or take the plunge and face the world.”

[From Us Weekly & People]

If you want some gross details about what it’s like to one of Hef’s multiple girlfriends when it’s time to get down with him in his bedroom, go here. She says there was no intimacy, no kissing and everything was over pretty quickly. Probably just in time to bring the old guy some post-coital SOUP. What else? Let’s see… Holly says she hasn’t spoken to Hef in four years. She says that every one of his girlfriends had body image issues while they lived at the mansion. Holly admits to getting a nose job while she was with Hef. Ugh.



Photos courtesy of WENN.

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62 Responses to “Holly Madison: Hugh Hefner offered me $3 million (in his will) to stay with him”

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  1. GlimmerBunny says:

    I used to watch “The girls next door” and she was always my favorite of the girls. I think it seemed like she and Hef sort of loved each other the most too. Oh well, goes to show that one again, reality TV is the opposite of reality.

    • Christin says:

      I watched a few episodes and recall she was clearly the one (of three) that seemed most serious about him, and vice versa. Never understood why she wanted him, but she certainly put on a good act.

  2. littlemissnaughty says:

    I feel like I’ve read all of this before?

    • Hannah says:

      You have. Many bunnies have written “salacious” tell alls that basically say I was a poor naive innocent victim and big old mean Hef set his sights on me and took advantage and made me watch old movies with him.

      • Sarah says:

        Keeping with Hanna’s line of thinking (which I agree with)…..these girls were victims because of course they had no idea who Hugh Hefner was nor what his reputation was nor any guess as to what might go on at the Playboy mansion.

      • anon33 says:

        Seriously. I am not sure what these people expect when you sign up to be a Hefner girl.

      • littlemissnaughty says:

        Okay so it was other girls. I thought she or one of the other two who were on that show with her had said something before. That whole “sex with Hef” routine seemed very familiar.

        On the one hand I agree that they chose this life and were not, in fact, prisoners in the Mansion. They were adults. On the other hand, this man had decades of experience manipulating young girls and women. I remember how Bridget was hoping that one day she’d make it into Playboy but Hef just kept stringing her along.

  3. vauvert says:

    I find it very hard to summon sympathy for any of these women. Were they forced at gun point to walk into the Playboy Mansion and have sex with that vile old man? There will always be rich, disgusting old guys willing to pay for young, pretty women… The women choose that lifestyle. What did she expect, a grand romance with a man her grandpa’s age? Ugh.

    • Brin says:

      Totally agree.

      • SnarkySnarkers says:

        I have always liked Holly. Is she a famewhore? Yep, but she seems like a fun girl to hang out with and I am also obsessed with all things Disney. I don’t feel sorry for her. You have to know what you are getting into with Hugh Hefner. I mean c’mon. This book sounds like the perfect summer beach read though and I think I’m going to go pick it up today.

    • WinterLady says:

      It definitely isn’t a new story, naïve young woman (women) being used, knowingly or unknowingly, by an old rich man. I guess it is also questionable for Madison to be selling the lifestyle she choose and they man who gave it to her out. Gotta’ get that money, I guess.

      • Hannah says:

        Ummm she used him too. And she sought him out, not vice versa.

      • WinterLady says:

        I agree, she used him to. She is still getting mileage on the story years later and is making money, among other tings.

      • LL says:

        By all accounts she went to LA to make it as an actress and model, failed, and was homeless sleeping on friends’ couches and working at Hooters when she decided to make it her goal in life to become a ‘Hef Official Girlfriend’ (which is a paid job, cash in hand weekly). She literally stalked him and learned everything about him so she could turn herself into his perfect woman, in order to achieve this goal. Pretending she studied the same subjects as him, studying his favorite movies, Single White Femaling his existing Official Girlfriends and having plastic surgery to look like them, etc etc.

    • GoodNamesAllTaken says:

      Yes, I have to try really hard not to judge. You will either sell your body or you won’t. If you do, you are an object to the buyer. To expect him to treat you as a person is unreasonable. People say oh she was young, she had no money, but I was young with no money at one time, and I honestly think I would have starved to death before I did that. She could have worked as a waitress or secretary or any lesser paying job, but she made a choice for easy money. She had a right to make her choice, but the outcome of that choice was obvious to me, even at that age. I guess the difference is that I was loved as a child and I had some self-worth. Perhaps she didn’t.

      • MelissaManifesto says:

        You’ve put it all so eloquently.

      • Lirko says:

        I know she has stated before that her father was super into Playboy as she was growing up (and very open about it), so maybe that, too could have factored into her decision making process, like in a sick way, she was looking for approval from her father,trying to make him proud of her.

      • WinterLady says:

        Going by her seemingly sincere attachment to Hef, I’d say it is pretty spot on to say she possibly has daddy issues.

      • Kitten says:

        Well said, Gnatty.

      • Gretchen says:

        @ GNAT I have a lot of sympathy for her. Considering her plastic surgery, diets and sexual experiences in the mansion it seems clear that she had no sense of self worth. I don’t think it is a coincidence that she along with all the other “girlfriends” all had body image issues, predators like Hef can sense this stuff a mile off and prey on those vulnerabilities. Yes, it was ultimately her choice to be there, but when you are being manipulated and your sense of self worth is entirely tied up with that manipulator, it can be hard to see the forest for the trees.

        Also, this might sound knit-picky but sex work isn’t selling ones body, it’s selling a service that your body performs. Paying for sex, is not paying for a person. Many people buy the physical services of other human beings and are still expected to treat them as people. Unfortunately sex work is viewed differently, the women are devalued, mocked and told well ‘what did you expect’…It’s a common response, although I do find it saddening (especially on this site), that this is seen as normal and ok.

      • LL says:

        I have to agree. I have some sympathy for Kendra who was only a teenager when she became a Girlfriend, and an obviously deeply troubled one at that (teen runaway, homeless, no relationship with any family, underage stripper and nude model, drug problems, had been incarcerated in a mental hospital). Even though being a Girlfriend seems to have been very good for her overall, it’s massively wrong and exploitative to pay a mentally ill homeless teen for sex.

        The other two not so much as they were both adults in LA to become famous, and in Bridget’s case she was supported financially by her husband and was with Hef just to try to boost her career.

    • ScrewStewRat19 says:

      No, they weren’t forced at gunpoint, but most people on this site call out Terry Richardson for his pervy ways and directors that like to use the casting couch. It’s all about power and being the one in control. While I agree any of these women could have said no and not given in to the temptations for fame, money and a cushy career, I can’t help but also blame the men in power who put them in this kind of position to begin with.

      • milla says:


        Young models do not know about TRs reputation, cos he works for major magazines. HH created Playboy. It is that simple. And speaking of using force, TR did that and he used manipulation on minors.

      • Kitten says:

        Young models know about Richardson’s reputation, believe me.

      • GoodNamesAllTaken says:

        Yes, I didn’t mean to imply that I give HH a pass. He just seems beneath contempt and mention to me almost. I have long thought he would be snubbed by pond scum as unworthy of pond scum’s notice. He makes my skin crawl. He’s a walking STD, an old creeper in a bathrobe paying for sex and soup. And you make an excellent point.

        The difference I see with TR is that he sort of takes the women by surprise, and leads them into more and more provocative photos, then all of a sudden assaults them in some way, like ejaculating into their face or some such. They usually say they were shocked and felt numb and didn’t know how to stop it. I’m not sure (I don’t know) if HH does that, or he’s more straightforward about what he’s doing. But they are both disgusting, and I didn’t mean to imply that it’s all on the women.

      • ScrewStewRat19 says:

        So because he created Playboy the young, naive women that probably have no worldly experience should know what they are getting into? Then every woman who tries to get into Hollywood or modeling should know better, because the rumors and stories have been out there for decades now. I guess I just see how easily a young woman with no real experience of being out on their own could quickly get wrapped up in that lifestyle and not see it for what it really is at first. I’m sure it’s really easy to project a certain image and get somebody hooked on that lifestyle only for them to later realize it wasn’t what it seemed.

      • ScrewStewRat19 says:

        GNAT, I wasn’t responding to you, so please don’t think I was coming at you with my comments. I agree with everything you said. Honestly when I first heard about Richardson and casting couches I thought the women were idiots. I didn’t understand how these women could let themselves get in these positions because I thought I would easily be able to say no. I’d never sell myself out like that for fame or whatever, but then I kept reading all of the comments about the position of power the men are in and all of the promises they can make and I really started to think about it. Most of these women are really young with no real experience of the world and are trying to make it on their own, they’re vulnerable. I doubt that HH is more straight forward about it. I’m sure he butters these girls up with delusions of grandeur before they really see what it’s like to stay there.

      • anon33 says:

        Well I’m sorry but no amount of money or lack thereof or number of reasons you could outline would EVER persuade me to do what these girls do. It’s the same thing with heroin-everybody knows it’s bad, I don’t want to hear that they don’t.

        And to Gretchen above: you can’t parse out them being sex workers as selling a commodity or a service and not their body, but then argue that doing so results in low self esteem and emotional damage. If they’re “just selling a commodity” how does that result in emotional damage? Shouldn’t they view it as “just a service?” I’m confused by your line of thinking.

    • milla says:

      they know who he is. they want the cow and the cash and I really cannot feel bad for them. they wanted to be famous for nothing. these women do not care about getting education, becoming independent, they are just as vile as HH.
      my sympathy goes to young ladies all over the world who are trying to become someone, not something, even though they were not born with silver spoon.

  4. Tifygodess says:

    I’ll read it, because I have no shame. lol I loved watching the girls next door. I doubt it will be as good as Playground though. ( a must read – a true story about a young girl growing up in the mansion who witnesses the dark side of playboy during its hay day )
    I also don’t think Holly is looking for sympathy ,she’s just telling and selling her story.

    • Felice. says:

      I’m gonna read it too lol. That show was my crack back in the day.

    • beautifulDay says:

      I am moderately obsessed with all things Playboy, because it was promoted as part of the “sexual revolution”, this free sex thing. However, it’s only “free love” for the men, and not the women. I’m also shocked that a reality tv show portrayed the girls as “silly” and or “serious” about “loving” HH, when the sex was condomless and spurred by viagra. The GND show seemed to “normalize” prostitution, which is the opposite of “free love” and nothing to do with a “sexual revolution” as prostitution is the oldest profession. I just find the whole twist of the HH product to be shocking, and the book Playground is just a cringey true tale of gender objectification. I like that Holly wrote her story, the who PB thing is frightening, not GND cutesy.

  5. Nicole says:

    Good for her for not letting this stuff stay a secret. He was a civil rights supporter, which is admirable, but let’s not forget that he made his fortune out of objectifying women. He’s stayed on the right side of the law but, you know, it’s fair to say he’s a creepy old bugger.

    • angie says:

      …objectifying women while pretending all the while to be staunch feminist. He’s gone from a slick, young satyr to a pathetic, decrepit satyr. What a worthwhile life. Why do people still go to his parties?

  6. MelissaManifesto says:

    I am not fan of Hugh Hefner, not because he has made a name and fortune in this industry, but how vile and disgusting I think it is for a man his age to be sleeping with so many women and treating them so poorly. That said, Holly Madison isn’t without blame, if we know about her now it’s because she was Hef’s main girlfriend, she milked the opportunity for all it was worth. Sure she can write a book now to gain our sympathy about how miserable her life was at the mansion, but she chose that life. Even then it does not mean that I can’t sympathize with her, it’s the way she is putting in our faces that irritates me.

  7. Sugar says:

    ‘Usually, I don’t approve of drugs, but you know, in the ‘70s they used to call these pills thigh openers.’

    Now we know why Hef and Cosby are friends…

    • JudyK says:

      Ouch! And right on target.

    • ozmom says:

      I don’t see it that way. I took it as a test to see how she would react and he said it was good that she turned him down. He didn’t then slip her something to knock her out and rape her while she slept. I don’t see any similarities between the two men.

  8. Lara K says:

    I’m just sad she only saw in hindsight what is painfully obvious from the outside. Glad she got out.

  9. Relli says:

    Interesting, I read the other book by a former girlfriend that came out years ago. Her time preceeded Holly with some overlap and I believe was cited as one of the reasons she was eventually kicked out. She actually put some stuff in there about the sexy times they all had with Hef and if true I can see why Holly was driven to having suicidal thoughts, shiver. I am glad Holly got herself out, it is not a good place for anyone.

  10. Cara says:

    Three million bucks would be a pittance to Hefner…not sure if she’s bragging or complaining… ???

    • FLORC says:

      Not really. His wealth isn’t as vast as you’d think. Not when it’s broken down. What he would have to hand out in cash/liquid assets isn’t as great.
      In total it’s estimated 43 million, but the majority of that is tied up and not his to just give away.

      Now comparred to Larry Flynt yea, 3 million is nothing.

  11. FLORC says:

    This was all very obvious on Girls Next Door.
    Holly even spoke often about how she wants another nose job because that’s what Hef prefers. Her layers of makeup also. And her daily diet for a time was a bowl of Bran flakes 3 times a day with several hours of working out. Everything she said and did was for Hef. To be what he wanted. It was disturbing and sad.

    • Kitten says:

      The idea that a guy would prefer layers of makeup is such a foreign concept to me.
      Maybe it’s just because I only associate with quality guys, but all the guys I know fall into the “less is more” camp when it comes to makeup.

  12. H says:

    What happened to Bridget? She seemed like the smartest of the three on that show. Hef is a creeper. I remember reading a book stating his “girlfriends” stood in line and climbed on top of him one after the other — no condoms. I felt like yelling, “This isn’t 1968, you old pervert!”

    • missmerry says:

      I loved Brigette. She was way too good for the playboy mansion, but kinda fit in there at the same time. She had personality, seemed genuine and loved to dress up and throw themed parties, which comes in handy at that place.

      she had the cutest laugh and her grumpy cat was hilarious.

    • Asiyah says:

      She was my favorite too.

    • LL says:

      She was married, had always dreamed of becoming famous and specifically of being a Playboy Playmate. She and her husband came up with a plan for her to move to LA, pretend to be single and much younger and that she’d focus all her energies for one year on getting into Playboy, while her husband would stay home and financially support her. Becoming a Hef girlfriend was part of that plan, which her husband was apparently okay with. She left once she’d achieved her goal of being in Playboy and becoming famous, apparently on very good terms with Hef.

      • Asiyah says:

        Wow! Interesting. She always seemed smarter than the other two. Not that I approve of this plan at all but it shows she’s more clever than I thought.

    • Hannah says:

      I would read a book by Bridget, she definitely seems the most honest about her wants and expectations, and the realities of why she was there. she was upfront that she knew he’d never put a gf in the magazine (because he’d learned that’s what many were there for), but she hoped she could wear him down. she marketed herself and she did it well. she hosts that exotic beaches show on the travel channel, has a relatively lucrative etsy and beyond apron business, and still designs “sexy” halloween costumes. She parlayed her notoriety into success beyond name recognition and did so while she was in the house.

  13. boredblond says:

    Paid off in his will? That’s like being told maybe you’ll be paid in ten years for work you’re doing now.. I have no real sympathy for any of the playboy girls..I can’t believe anyone is so naïve they don’t know what’s going on, but am surprising myself because I actually am thinking about reading this book…crazy, eh?

    • beautifulDay says:

      That’s the twist…to uneducated women, HH promotes his antics as “the sexual revolution” and an” expression of feminism”. When I was a dumb young thing I was put off by the platinum hair and pink outfits. The aversion came first and the education came later, but many young girls are sucked in by the twisted logic. I -do- pity the women who want to be a sexy bunny, it’s tragic to use the sexual urge to suppress any person’s freedom.

  14. kri says:

    ohbarfbarfbarf. Ugh.You couldn’t even use condoms with him because his sperm are probably dust poofs. You’d need a Swiffer.Gross. Brain bleach, please.

  15. Naddie says:

    No pity over her, but I support her decision to speak out, even if it’s just for attention.

  16. Velvet Elvis says:

    This is Holly’s story to tell so yeah she should be able to tell it, but she is clearly trying to paint herself as some kind of victim when she really wasn’t. She could have left at any time. Any decent woman would have. And there’s something unseemly about going into details about the sex and Hef’s sexual prowess. That feels like a huge invasion of his privacy. She used him to get a lifestyle and a career and continues to use him by writing this book.

  17. Ava says:

    Ugh….I have no sympathy. She is not speaking out to help others. She is speaking out to make money. She is using him as much as he used her. I watched the show. She gushed over him. She isn’t that good of an actress. She is writing a book now to get her name back out there. All she did after the mansion was her live peep show….big change after escaping the mansion…..

  18. Kelly says:

    Really no sympathy for her. She was an adult who chose to stay with him and have a TV show focused on her after this suicide attempt. I’m sure it was challenging to live there but she used it as a means to support herself and further her career. No one forced her.

  19. Asiyah says:

    You forgot to include the juicy tea she spilled on Kendra. It’s funny that she says Kendra was fake because I found myself thinking that the entire time I was watching “Marriage Boot Camp” last week.

  20. enike says:

    I am on the fence with Hugh.
    Wasnt he the person who let ALL people get into his night club front door back in the time, when it was “not preferred” or something? Contracting singers, who would not get a gig, because of some prejudice?

    Starting a relationship with him and moving to the mansion – who in their right mind would do this?

    On the other hand, expoiting young bimbos, who were dumb enough to do it, was not right. But…. how dumb you must be to sleep with a man, if you are 20, the man is about 60, and you have to sleep with him with 10 other girls at the night?

    Holly seemed genuine and sweet. I really liked her. How low is it to publish this drivel?

    I am going to wait, what aspect will prevail (the innocent girl story or the human rights angle)

  21. Caz says:

    Do we need any further proof that the Playboy myth is a defunct & obsolete notion/brand/product?