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Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny

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by Holly Madison




  Table of Contents

  DEDICATION

  EPIGRAPH

  Dedication

  Epigraph

  The Playboy Mansion and Grounds

  Author’s Note

  Prologue

  CHAPTER 1

  CHAPTER 2

  CHAPTER 3

  CHAPTER 4

  CHAPTER 5

  CHAPTER 6

  CHAPTER 7

  CHAPTER 8

  CHAPTER 9

  CHAPTER 10

  CHAPTER 11

  CHAPTER 12

  CHAPTER 13

  CHAPTER 14

  CHAPTER 15

  CHAPTER 16

  CHAPTER 17

  Photo Section

  Acknowledgments

  About the Author

  Credits

  Copyright

  About the Publisher

  THE PLAYBOY MANSION AND GROUNDS

  AUTHOR’S NOTE

  PROLOGUE

  CHAPTER 1

  CHAPTER 2

  CHAPTER 3

  CHAPTER 4

  CHAPTER 5

  CHAPTER 6

  CHAPTER 7

  CHAPTER 8

  CHAPTER 9

  CHAPTER 10

  CHAPTER 11

  CHAPTER 12

  CHAPTER 13

  CHAPTER 14

  CHAPTER 15

  CHAPTER 16

  CHAPTER 17

  PHOTO SECTION

  ACKNOWLEDGMENTS

  ABOUT THE AUTHOR

  CREDITS

  COPYRIGHT

  ABOUT THE PUBLISHER

  DEDICATION

  TO MY FAMILY,

  WHO INSPIRE ME TO BE A BETTER PERSON

  EPIGRAPH

  Thus grew the tale of Wonderland.

  —Lewis Carroll, Alice’s Adventures in Wonderland

  CONTENTS

  Dedication

  Epigraph

  The Playboy Mansion and Grounds

  Author’s Note

  Prologue

  CHAPTER 1

  CHAPTER 2

  CHAPTER 3

  CHAPTER 4

  CHAPTER 5

  CHAPTER 6

  CHAPTER 7

  CHAPTER 8

  CHAPTER 9

  CHAPTER 10

  CHAPTER 11

  CHAPTER 12

  CHAPTER 13

  CHAPTER 14

  CHAPTER 15

  CHAPTER 16

  CHAPTER 17

  Photo Section

  Acknowledgments

  About the Author

  Credits

  Copyright

  About the Publisher

  THE PLAYBOY MANSION AND GROUNDS

  AUTHOR’S NOTE

  Don’t you miss the mansion?” squealed a round-faced, wholesome-looking 20-something girl in a high-pitched voice.

  “Um,” I started, unsure of how to answer her politely. “No . . . ?” I said, offering her a halfhearted smile.

  Here I was, an independent, successful woman, making millions of dollars a year (all on my own), headlining a hit show on the Las Vegas Strip, coproducing and starring in my own television show, and this woman was asking me if I missed the mansion?

  Clearly the public perception of the life I shared with Hugh Hefner at the Playboy Mansion was a far, far cry from the actual reality I experienced.

  This question wasn’t really that uncommon. Fans would regularly ask me about my time living what they assumed was this lavish, decadent life in Holmby Hills and whether I regretted my decision to leave.

  “Hef really fucked up when he let you go,” a young fan said, shaking her head, at a Las Vegas meet-and-greet. That was another one I was regularly on the receiving end of.

  “It’s okay,” I would always say. “I’m much better off now.”

  I couldn’t—and still can’t—believe that these adult women were actually serious. While filming the E! reality series The Girls Next Door, I never thought of myself (or my two costars) as role models or anyone to be taken seriously.

  I thought people were just laughing at us. I thought of us as walking advertisements: “Don’t try this at home, kids.”

  I’m not stupid. I know how unsavory that whole situation was. You could read it all over my unsmiling face. Cameras often caught me rolling my eyes or looking totally uninterested. As if I didn’t feel trapped enough, I built up a wall around me. I’d gotten myself into a bad situation, but I became distinctly aware that was not the impression fans walked away with.

  The show was the epitome of mindless reality television, which was fine. We all have our guilty pleasures that we like to unwind with at the end of the day. There is something underneath the surface that isn’t okay about it, though. Around the turn of the millennium, it became fashionable for women to appear stupid—to get by solely on their looks and to be concerned only with fame and materialism. Some of the effects of that moment in the zeitgeist still linger today.

  And somewhere along the way, I too bought into the ludicrous fantasy . . . perhaps even more so than others.

  While there was a part of me that acknowledged the idiocy and superficiality that surrounded me, I fell for the glamour: hook, line, and sinker. It took years for me to realize just how manipulated and used I had been. I could never admit that to myself at the time, because to do so would have been to acknowledge how dark and scary a situation I was in . . . and how very little in control I was.

  “I’m an adult. I’m here because I choose to be. I’m here for adventure, a once-in-a-lifetime experience. I’m here as a stepping-stone to something else,” I routinely told myself. And perhaps the biggest disillusion: “I’m here for love.”

  Deeper and deeper I fell down the rabbit hole.

  Many people may think that I’m biting the hand that fed me and that I should be grateful for the opportunity Girls Next Door and Playboy afforded me. And while I am grateful, it’s also clear to me that most people fail to realize that there are two sides to every coin and that even the most fantastic fairy tale has a dark underbelly. Being attached to Playboy can make people not want to have anything to do with you, even in quirky, crazy Hollywood. There were many times the hateful backlash made me wish I stayed the broke, awkward 21-year-old waitress I’d been before Hef came into my life.

  When I finally did find the strength to leave the mansion, I began receiving lucrative offers to reveal my version of events, but I never pursued them. I wasn’t interested in writing a sensational tell-all for the sole purpose of exposing someone else’s strange habits and dirty secrets (don’t worry, you’ll find those things here, but in the context of something bigger). I wanted to have my own story to tell, too.

  To this day, it astounds me the number of misconceptions that abound about my life and my experiences while at the mansion. Usually, the version of the story most flattering to Hef is the one that prevails.

  I’ve seen both sugarcoated and sensationalized accounts of life at the mansion, but nothing I’ve ever read remotely resembles what I actually experienced. I always thought it would be classy to not kiss and tell . . . but after a while you just get sick of having other people trying to tell your story for you.

  Hopefully, once you read my story, you will be able to understand why I made some of the choices I made . . . and why I also felt trapped by those choices. I hope that sharing my mistakes can prevent someone else from making similar ones, or give someone the courage to leave a bad situation.

  This starts off as your typical “Small-Town Girl Goes
to Hollywood” story that we’ve all heard a hundred times before. But it’s also much more than that: it’s the unauthorized, never-before-told story of the Playboy Mansion and the man that holds the key; it’s a behind-the-scenes account of reality television at its most decadent and absurd; it’s a cautionary tale; it’s the story of betrayal and abuse but ultimately of survival, success, and redemption; and finally it’s a real-life fairy tale with heroines, villains, odd characters, strange happenings, and, of course, a “Happily Ever After.”

  Some of the names in this book have been changed to protect the innocent . . . as well as some of the not so innocent. When you’ve journeyed into a dark world where publicity and fame are commodities so deeply desired and unable to be bought, you’re hesitant to give some of those people who have hurt you the attention they so desperately crave. But I am here to set the record straight: the good, the bad, and the ugly. The naked truth. I was born a girl with an insatiable appetite for the extraordinary: the strange, the unusual, the glamorous, and the morbid. And I experienced all of it.

  So follow me down the rabbit hole . . . the truth may be stranger than you imagine.

  PROLOGUE

  “I know who I was when I got up this morning, but I think I must have been changed several times since then.”

  —Lewis Carroll, Alice’s Adventures in Wonderland

  1988

  It wasn’t the most lavish-looking present under the tree. The flat, square package was wrapped in simple green and white paper with a glossy red drugstore-bought bow and addressed to me from my aunt.

  When I was nine, Christmas wasn’t necessarily the spectacular event it had been in years past. I wasn’t particularly interested in toys anymore, but I wasn’t yet mature enough to appreciate the more practical presents.

  Holding the soft object in my hand, I didn’t expect much.

  Carefully, I peeled away a corner of the paper to reveal what appeared to be the bright blue cover of a book. With a bit more eagerness, I tore away the remaining wrap and read aloud the words: Marilyn Monroe Paper Dolls.

  Of course I had heard of Marilyn Monroe before. Madonna had spent most of the ’80s replicating the movie star—most memorably in her 1985 Material Girl music video—and like most fourth-grade girls, I idolized the pop singer. But I don’t recall ever seeing Marilyn before this moment.

  Smiling up at me from the cover of this gorgeous book were two illustrations of the starlet: one dressed in a black-sequined showgirl costume and top hat from her 1953 movie Gentlemen Prefer Blondes and one in a casual pink sweater and capris with flowing blond curls from 1952’s Clash by Night.

  Flipping through the thick, glossy pages I saw a variety of costumes from her most famous roles: a pageant swimsuit with sash and tiara from We’re Not Married (1952); a cream gown with a pink and purple, frilly kimono wrap from The Prince and the Showgirl (1957); a green and yellow Bo Peep–inspired ensemble from one of her earliest roles; and so many more.

  More than 30 different costumes (including one of the starlet in nothing but a bathrobe draped over her otherwise naked body) filled the pages to dress the bikini-clad Marilyn Monroe cutout figure. On the back of the book was a biography, detailing how the orphan Norma Jeane became one of the world’s greatest movie stars.

  With extra special care, I methodically cut out the figure and each of her glittering outfits. I spent hours dressing and re-dressing my Marilyn doll, imagining how she must have felt in each moment: the weight of those gilded gowns, the sounds of an active movie set, the wondrous eyes of the countless admirers, and the decadent Hollywood parties I could only dream about.

  My little world felt so limiting. As my family bounced from Oregon to Alaska, then eventually back to Oregon again, no place ever felt like home. I grew up hunting, fishing, reading, and playing in the woods in Alaska; when I arrived in Oregon I was a fish out of water. The kids in my new school loved two things and two things only: sports (which I had never played) and video games (which I couldn’t afford). Not to mention, my social skills were lacking. I frequently tried to reinvent my image, my group of friends, and my hobbies, but nothing ever felt like me. The other kids treated me like an outsider because they thought I was different.

  They were right—I was different. I dreamt of a world outside my little rain-soaked suburban bubble. I’d fantasize about a glamorous career and all the amazing costumes I would wear one day. I thought that if I wished hard enough, perhaps I would fall down the rabbit hole and find myself in a decadent world beyond my wildest dreams.

  And Norma Jeane Mortenson did that—didn’t she? She escaped her boring existence and became Marilyn Monroe.

  Quickly, my fascination with the star escalated. Every Sunday morning, I would grab the newspaper and pull out the TV guide. My eyes would scan over the programming list searching for the titles of any of her movies listed in the book.

  The first one I finally came across was Bus Stop (1956). I set up our family VHS player to record it when my parents weren’t looking. They let me keep the paper dolls, but they didn’t really care for Madonna or Marilyn or such frivolous fascinations. I found that first film a little dull—some of the nuances in Bus Stop went right over my nine-year-old head. After all, they couldn’t always spell everything out in the 1950s.

  As weeks became months, my VHS collection grew and I became acquainted with most of Monroe’s better-known pictures. How to Marry a Millionaire quickly became my favorite, mainly for the campy 1950s fashions on screen.

  Yes, I know what you’re thinking. I’m almost embarrassed to admit that because of the film’s title, but the title and plot had nothing to do with why I liked it. I loved the three main characters. They were just too irresistible: model roommates played by Lauren Bacall (the smart one), Marilyn (the romantic one), and Betty Grable (the athletic one who always said what was on her mind).

  As for Marilyn herself, I was absolutely enchanted with the glamorous creature whose beauty transcended the small television set in my family’s living room. On screen, she appeared to have everything she ever dreamed of: fame, beauty, fortune, and, of course, love.

  Someday I’ll know what it’s like, I thought. Someday I’ll know what it’s like to have it all.

  2002

  If I just put my head under the water and take a deep breath in, it would all be over, I thought. The bathroom was empty as I swam alone in the giant marble tub. The air was chilly inside the mansion walls, with a draft that always seemed to rustle through the rooms. I pulled my shoulders under the warm water and rested my stoned eyes on the wall opposite me. But could I really do it? I dipped my toes in and out of the water and listened for the quiet echo the splash made as it bounced off the tile walls, feeling like an exotic fish trapped in some enormous aquarium. Outside the bathroom, the mansion was eerily quiet.

  It was unusually calm at this hour of the night. We spent yet another evening out at one of Hollywood’s hottest nightclubs (like clockwork, we went clubbing every Wednesday and Friday), before coming home and retiring to Hef’s room, where we all smoked weed and went through the weird bi-weekly “bedroom routine” (which was nothing like most people imagined it to be). To an outsider, our evenings looked incredibly glamorous: seven beautiful women dancing the night away behind velvet ropes and bulging security guards, private table service to cater to our every desire, and exclusive access to the club—all at the expense of the world’s most notorious boyfriend: Hugh Hefner. But if you looked close enough, each girl appeared to be just a little bit vacant and merely going through the motions of what life ought to be. Life inside the mansion wasn’t at all what I expected to be—not even close.

  Everyone thinks that infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in. I wasn’t quite sure how I ended up in this curious, often dark world, but I was petrified by my own fear of what it would mean to ever leave. Tucked away inside Hugh Hefner’s rolling Los Angeles estate, I was controlled by a spur-of-the-moment decision
I made at 22 years old that I had grown to deeply regret despite the extravagant world it afforded me. It was a decision that changed the course of my life.

  I had to believe that there was a greater purpose for the choices I had made: whether it was to help advance my career or whether it was truly for love. And depending on the month, the week, and sometimes even the hour of the day, I would waffle back and forth between precisely why I was living a life as nothing more than “Girlfriend Number One” to a man who was old enough to be my grandfather. I didn’t want to admit that I had sold a bit of my soul for the chance at fame.

  Would anyone even miss me? It’s amazing the dark places your mind can wander when you’re depressed. The depths of my own depression had led me down this very dark path, and there was no gleaming light, however distant, at the end of this tunnel. Maybe it was the pot and the alcohol, but drowning myself seemed like a logical way to escape the ridiculous life I was leading. I just couldn’t take my misery anymore. Of course my family would be devastated, but I rarely saw them enough for my absence to make a difference.

  From a distance, it appeared as though the girlfriends’ days consisted of bopping around Beverly Hills shops, driving flashy cars, and toting designer handbags. I played the part of the perfect girlfriend well: a bubbly, fun-loving, carefree girl who loved her dogs, her lifestyle, and, most important, her boyfriend. Playing that role quickly became second nature, and the blurred lines of reality made it so that some days I struggled to even remember what I was like before moving into the mansion. It was like a high-stakes version of teenage politics: sometimes you try so hard to fit in that you almost forget it’s all an act. I was afforded many things while I lived in the Playboy Mansion . . . but never the opportunity for the sort of self-discovery most 20-somethings enjoy.

  Public criticism and speculation have always trailed Hef and his harem of young, blond girlfriends: “Do they all sleep with him?” the more conservative folks would wonder. “It’s all an act. They’re just paid to be arm candy,” the younger crowd would usually surmise. “How does he keep up with them all?” the older men marveled. But life inside the Playboy Mansion wasn’t exactly the sexy fairy tale my ex-boyfriend would have you believe. In fact, it was like a bedazzled, twisted prison where the inmates developed their own hazing and hierarchy and where the release back into society was the equivalent of being excommunicated.

 

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