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

by Holly Madison

  How would the other girlfriends react to my death? Among the seven girlfriends, I had only one friend: Bridget Marquardt. Surely she would be distraught over my death, but I couldn’t imagine the others girls would shed even a single tear. The climate inside the mansion was toxic. I didn’t participate in the cocaine benders, the side boyfriends, or all their harebrained moneymaking schemes that were all in direct violation of Hef’s house rules. I rarely left the mansion, so making it home in time for curfew was never an issue either. Needless to say, my goody-two-shoes reputation wasn’t the most welcome among this group of girls. In fact, they’d probably view my unexpected demise as an opportunity to get away with more shit as Hef busied himself with the public relations rollout regarding a death at the mansion. Not to mention, it would mean less competition. Yep, they would be glad I was gone.

  Would Hef even feel bad when he heard the news? He’d probably be completely shocked. In his eyes, as long as each girlfriend had a substantial allowance to buy nice things—and the ability to bask in the reflection of his fame—that’s all she needed to be happy. He would surely never concede that my misery had anything to do with him or the life he provided. Would he even miss me? No, I was certain I was just another warm body—as we all were. “Just another blonde,” I could hear him say. Internally, I decided he would label it a devastating accident. His main concern would be navigating Playboy out of any sort of PR crisis. A small memorial might even be held at the mansion, but it would glorify my days at Playboy and with Hef, once again promoting the idea that life inside those walls was nothing short of paradise.

  And just like that, I would be swept under the rug with every other scandal and ghost that once plagued Hugh Hefner . . . and my memory would involuntarily serve as yet another public reminder of the beauty that is Playboy.

  I think that knowing my death would be in vain convinced me not to go through with it. In truth, I didn’t really want to die, but I saw no other way out. Thankfully the only thing greater than my need to escape was my desire to share my experience. If I sunk my head below the water and went to sleep, no one would ever know the truth.

  Eventually I’ll tell my story, I thought. I wasn’t sure when and I wasn’t sure how, but someday I would fight my way out. Someday I would be whole again.

  CHAPTER 1

  “Begin at the beginning,” the King said, very gravely, “and go on till you come to the end.”

  —Lewis Carroll, Alice’s Adventures in Wonderland

  Slowly, the large iron gates surrounding the infamous compound creaked open and our shuttle began its ascent up the steep driveway. My nose was pressed so tightly against the window—anxious to spot any sign of the luxurious Holmby Hills estate expertly hidden by the lush foliage—that my makeup smudged on the glass. Over my shoulder, I heard a fellow partygoer point out the first glimpse of the 20,000-square-foot Gothic Tudor that was steadily coming into view.

  “There it is!” a man in silk pajamas shouted. I craned my neck to spot the roof and fixed my eyes on the horizon as the mansion began to surface. Like an early morning sunrise, it was magic. The estate—situated on five rolling acres in one of L.A.’s most prestigious neighborhoods—looked like a castle from a fairy tale. My large eyes widened, trying to fully absorb this moment.

  As the shuttle reached the top of the driveway, my girlfriend Heather spotted the infamous “Playmates at Play” sign and nudged me in the ribs.

  “Look!” she said, her smile so large I thought it was about to snap off her cheeks. We both burst into laughter. We were positively giddy. We are actually here, I thought. I made it to the mansion. It had become a goal of mine to see the inside of these walls, and I told myself that I could now happily check that one off the bucket list. I even wondered if I would meet Gatsby himself . . . Mr. Hugh Hefner.

  MY STORY WASN’T ATYPICAL: a small-town girl—farmer’s daughter, so to speak—who dreamt of becoming someone extraordinary.

  There were less than 10,000 residents in my hometown, and my high school graduating class was smaller than the guest list to most Hollywood parties (since then, it has seen a boost in tourism thanks in part to the Twilight movies, but let me assure you, there was no Edward Cullen sauntering through my lunchroom).

  After graduation, I moved 30 miles away to attend Portland State University. Which didn’t feel far enough, but it was the best I could do.

  It was early 1999 and I was in my second year in college when I heard on the news that Playboy’s “Millennium Playmate” search was coming to Portland. Immediately, my mind started to wander. I found Oregon’s weather depressing and didn’t feel like opportunity exactly lurked around every corner there. I had been thinking a lot about moving to Los Angeles to try my luck, but I didn’t know anyone in L.A. or have the financial means to make such a big move.

  Apparently, according to the report, the magazine had been conducting a nationwide “on the road” search for the “Millennium Playmate.” A gigantic tour bus traveled the United States (and Canada), stopping in 45 cities testing candidates. The girl chosen would receive $200,000, would appear inside the January 2000 issue of Playboy, and would be flown around the world to represent the men’s magazine for the entire year. It sounded like just the opportunity I was looking for!

  This wasn’t the first time Playboy popped up on my radar. As was true with many children of the ’80s, it wasn’t abnormal for us to have a Playboy magazine arrive at the house. I even remember my mom and dad studying the front cover of a Playboy once to find the hidden rabbit head. As a kid, you think that sounds like a pretty fun game, but we were quickly told that it was “for adults only.” One day my sister and I were scouring the house for any Christmas presents my mom may have hidden when we came across a few Playboys that had been hidden away. We flipped through in absolute hysterics, pointing out all the bare butts. I was a kid, so I thought it was hilarious!

  While Playboy wasn’t completely foreign to my home, it still felt rebellious. I knew that if I auditioned for the “Millennium Playmate” and happened to be chosen, my parents wouldn’t be thrilled at the prospect of me posing naked, but possibly would have respected my decision. It was a reputable magazine with a storied history, so it felt edgy but also somehow safe.

  Plus, at the time many of Hollywood’s biggest stars were appearing in the magazine: Cindy Crawford, Jenny McCarthy, Drew Barrymore, etc. Not to mention, my icon Marilyn Monroe was Playboy’s first ever cover girl. Naturally, I too had pipe dreams about one day being in the magazine.

  This is perfect, I thought. I’m going to audition!

  According to the news report, the process was quite simple: call the provided number, make an appointment, and show up with your favorite bikini.

  That’s when my genius idea to fast-track my stardom hit its first speed bump: I didn’t actually own a bikini. In my defense, I lived in Oregon. Why would I need a bikini? And when I say things were tight financially, I mean they were tight. But I decided it was about time to make an investment in my future. After calling the number, getting the address where the bus would be stationed, and securing an audition time the following week, I went shopping.

  Needless to say, Portland wasn’t brimming with retail shops specializing in swimwear, but I remembered seeing one downtown near my college campus, so I popped in to see what I could find. I didn’t really know where to begin. Obviously, I had never taken photos in a bikini before (this was about 15 years before “selfies” became popular), so I didn’t know what I should be looking for. After scouring the racks for the best deal, I decided on a silver metallic bikini that was both sexy but also one that I felt reasonably comfortable in.

  Before the audition, I figured I should probably get some kind of tan. There weren’t too many sunny days in the Pacific Northwest, so my complexion was incredibly light (particularly when coupled with blond hair and a silver swimsuit). I went to the nearby tanning salon and had my first experience with a tanning bed. I was terrified of going to my audition brig
ht red, so I asked for the lowest possible voltage. It wasn’t a drastic difference, but it did the job.

  As I pulled into the address I had been given, I spotted the tour bus immediately. It was so large that it stood out like a sore thumb in the hotel parking lot it was stationed in. When I arrived, I was ushered inside the hotel lobby with the other “potential playmates” to fill out some paperwork before stepping onto the bus for the audition. Over my new metallic bikini, I wore a barely above-the-knee black “miniskirt” and a white button-down blouse in hopes of capturing that “girl next door” image photographers were apparently looking for. And, to be honest, it was also the sexiest outfit I owned.

  To tell the truth, I was a bundle of nerves; I had never modeled before, so the idea that I’d be posing practically nude was terrifying. But I figured that since editors were hoping to discover new talent, they were expecting girls to be relatively inexperienced. On the bus, I envisioned a few stylists helping candidates with hair and makeup touch-ups and a distinguished photographer guiding the amateur models into the most flattering poses. Don’t get me wrong, I knew it wasn’t a full-blown shoot, but I expected at least a little help. It was Playboy, after all.

  After a few minutes of waiting, I was escorted to the gigantic 45-foot-long tour bus with two other girls. We were made to wait in the ultra-lux “living room” area, which was wrapped in leather with a seven-foot movie screen in the back. I remember thinking that it was nicer than any home I’d ever been in. Framed portraits of Playboy’s most iconic covers hung on the walls that reached up to a mirrored glass ceiling. A man with a clipboard walked into the room and greeted us. He gave us a brief history of the magazine and then asked that we go around the room and introduce ourselves and say why we were there.

  One girl looked like a Pamela Anderson–inspired stripper with white poufy hair, a clingy silvery dress, and clear-plastic platform heels (and appeared to have brought her pimp with her). For a moment, I remember wondering if she was actually a female impersonator. There weren’t too many women like her running around Portland at the time and I was so distracted by her appearance that, for the life of me, I can’t recall a single thing she said.

  The other girl was pretty, but not too remarkable, and I’d guess about 10 years older than me.

  “I came to try out because I’ve always wanted to be a Playmate,” she gushed. The man with the clipboard smiled and nodded, pretending not to have heard this response more than 20,000 times already. “And me and my best friend have a bet on who would become one first. I want to be Miss April.”

  Then it was my turn.

  “I’ve always dreamed of moving to Los Angeles and becoming an actress,” I explained, the other two candidates glaring at me. “I love Marilyn Monroe and she was the first Playmate, so that’s why I want to be in Playboy.”

  For some reason, each of us believed we were total shoe-ins. I mean, I really thought I had a shot. Knowing what I know now, though, none of us ever stood a chance.

  After the meet-and-greet, each girl was called one by one into the onboard “photo studio.” When my name was called, I stood up and pressed the creases out of my skirt before making my way into the room.

  It all felt very rushed. Besides the photographer, the room was empty—no stylists or coaches to speak of.

  “Hi, Holly, how are you?” the photographer said, staring down at my application in his hand and guiding me towards a white backdrop. “This will be great. Just relax. Have fun.”

  I was instructed to strip down to my bikini for the first photograph. Brimming with nerves, I did what I was told.

  “Awesome, great,” the photographer said hurriedly. “Now, can you take off your top?”

  Oh shit! He wants me to do what? I thought. He’s not going to take pictures of my boobs. Is he?

  It was incredibly naïve; I know that now. I had figured that the first round of photos were just to see if you were cute enough to be called back and then perhaps we’d discuss the possibility of more revealing photos. I wasn’t expecting to get naked at that very moment.

  Begrudgingly, I shed my top for a photo. Given how incredibly awkward I felt, I can’t imagine it was the most flattering photograph. Immediately, I felt the urge to do some kind of damage control. I had signed my life away on the photo release, so could they use these photos even if I wasn’t selected?

  “Um,” I said, clearing my throat. “Could you make a note or something that you don’t have my permission to use these pictures unless I’m selected?”

  The photographer gave me a weird look, clearly not expecting that kind of reaction from a girl auditioning for Playboy.

  “Okay, I’ll make that note,” he said before scribbling something down on my application. That was it, ten minutes and I was done.

  Now looking back, I don’t think I could have done anything more damaging to my chances. “Hi, I’m Holly. I want to be in Playboy but don’t use my topless photo.” But at the time, I wasn’t prepared for it. Of course I had hopes of becoming the “Millennium Playmate,” but I sure as hell didn’t want a topless photo of myself snapped in the back of a bus to be printed in the magazine (worrying about it appearing online wasn’t even a consideration back then). What if they did a spread of all the girls that auditioned?

  Not too surprisingly, I never heard a word from them.

  When the Millennial Playboy issue eventually came out, a set of Peruvian twins graced the centerfold (the girls were models from Miami who never even stepped foot on the Playboy bus; the “tour” was mostly a publicity stunt for the January issue).

  Wow, twins! I thought. I never stood a chance.

  In the previous issue was a four-page spread called “Girls of the Millennium Search” showcasing collages of nude photos from the girls who auditioned on the bus. It was exactly the type of story I wanted to avoid. Frantically, I scanned the pages but didn’t see my photo anywhere.

  Thank God I said something. Although after signing the paperwork, I’m pretty sure the editors could have done whatever they wanted with my photo. Yet, while I didn’t want to end up in some throwaway section of the magazine, I had to admit I felt a bit defeated. I thought I’d blown my opportunity to appear in Playboy.

  It wound up being six years—and a very strange twist of fate—before my next chance at a pictorial.

  In the meantime, I’d decided to transfer schools so I could make my way to Los Angeles.

  Before I left, however, there was one thing I needed to do.

  I TOOK A DEEP breath as I plunked three brand-new credit cards down on the receptionist’s desk. Like every college student, I had received a slew of credit card offers in the mail and applied for as many as I could get. Since the limits were so low, it took three cards to cover the $7,000-plus my new set of breast implants would cost me.

  As each card swiped through the machine—maxing out one after the other—I carefully filled out the paperwork with nervous excitement. You might think my failed Playboy casting was the reason I was now sitting in the doctor’s office preparing for an expensive cosmetic procedure, but that was really just the straw that broke the camel’s back. For the past several years I had struggled with insecurities about my chest—or lack thereof. I’d always been naturally curvy from the waist down, but from the waist up, I was as skinny as a stick figure.

  This had plagued me through high school and I spent those years perpetually armed with a heavily stuffed Wonderbra. I wasn’t trying to appear stacked per se—I was just trying to balance the proportions of my body while I waited for the bombshell chest I was certain I would one day develop. I remember gaping at Anna Nicole Smith’s GUESS ads when I was in junior high, hopeful that I would be just as voluptuous one day, but it never happened. (I even sent away for herbal supplements “guaranteed” to increase your chest by two cup sizes! Surprise! They didn’t work. I actually called and got my money back.)

  The nurse led me into the preop room and instructed me to change into the scratchy hospital gown. I
had never had even the most minor surgery before, but I was young, fearless, and determined to look my best. After all, you only live once, right? I was sure I would pay the credit cards off in a timely manner. It was no big deal.

  After the procedure, I woke up feeling like I had been run over by a garbage truck. The doctor had made the surgery sound so simple during my consultation that I actually thought I would be up on my feet that same day. Foolishly, I planned on keeping the entire ordeal a secret from my parents. I wasn’t in the habit of discussing my private anatomy with my mom and dad, and since I’d been stuffing my bras religiously for years, I figured they wouldn’t even notice. There was no way they would have allowed me to pile on all this massive credit card debt in one swoop, but I didn’t want to hear anyone’s advice (I was always one of those stubborn kids who insisted on learning things the hard way).

  The nurse rolled me out of the facility in a wheelchair to meet my friend who was scheduled to pick me up. Slumped over in the passenger seat, I realized there was no way I could keep this from my parents. After she pulled into the driveway and walked me to the front door, I not so gracefully stumbled through the entryway and flopped on my parents couch, clutching a barf bag full of bile to my chest. In this state, I had to explain the whole ordeal to them as they shook their heads with a mixture of amusement and amazement. Luckily for me, I had long been rebellious and they were used to my crazy antics.