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

by Holly Madison

  But I suppose I had already made up my mind at that point. Looking back, I can’t imagine what I was thinking, but I’m also so far removed from what I was feeling back then. I was about to be homeless. I had no place to go and was panicking over what to do next when this opportunity with Hef just sort of fell into my lap. If I became a girlfriend, I would have somewhere to live. If I became part of Playboy’s inner circle, perhaps that could even help my career. It felt as if my stars were starting to align. I decided to take the chance and see what this strange, legendary world was all about. For as long as I could remember, I had been searching for a great adventure, and this was already the craziest night I’d ever experienced. Like watching a bizarre old movie, I was utterly transfixed by this strange universe.

  Despite my initial intention to keep a clear head, I foolishly proceeded to get really, really drunk without even meaning to. I can’t even begin to tell you how much vodka and champagne I consumed—aided by the helpful hands of the other girls, who were all too eager to continue plying me with drinks. While I patted myself on the back for turning down the pills, by the time we left the club, I couldn’t have been any more incoherent.

  On the limo ride back to the mansion, Candice leaned over and whispered to me that all of the girls, myself included, were expected to join Hef in his bedroom. She had a small smile on her face as she watched me absorb this news, which I immediately registered as odd . . . almost as if she relished my shock. For the better part of the year, the girlfriends went out of their way to convince me that no one was actually intimate with Hef. Was Candice just trying to scare me off?

  I wasn’t an idiot. Despite their staunch denials, it was still a widely accepted public theory that Hef slept with all of his girlfriends. But when I asked them about it directly, they were incredibly convincing, acting almost appalled by the idea. This important factor was the touchstone of their entire sales pitch, and the fact that sex would actually be required wasn’t exactly something I had prepared myself for—especially for my first night out. But at that point, I felt like it was my only option.

  Maybe it wasn’t that torturous, I thought. Why else would all these pretty young girls be jumping through hoops to be girlfriends? I could just see what it’s all about. If it’s that bad, I’ll leave.

  What happened next is all sort of a haze. With roughly a third of a bottle of vodka sloshing around my stomach, I stumbled up the mansion’s grand staircase and was ushered by the girls towards Hugh Hefner’s bedroom suite. Tina brought me into the back door of the bedroom, which led into the large black and yellow bathroom. All the girlfriends—in various stages of undress—conglomerated around the large black marble bathtub with their feet dangling in the pool of hot water. I followed Tina’s lead, took off my shoes, and dipped my feet in. I have to say, after a full night of dancing (in very high heels!), the hot water felt amazing.

  Before I even had a chance to register much of what was going on, the girls quickly got up and hightailed it into the dark, cavernous room beyond. (They all hated the bedroom routine and tried to get it over with as quickly as possible.) Tina handed me a pink flannel pajama set to wear, which matched the ones all the other girls were grabbing out of Hef’s massive closet area. (Yes, Hef’s harem wore flannel pj’s. How’s that for a fantasy?)

  As Tina led me into the bedroom, I stumbled over and weaved through massive piles of junk covering the floor. It appeared that Hef liked to collect more than just women. Ceiling-high piles of videotapes, stuffed animals, art, and gifts littered the room. It was like an episode of Hoarders. But perhaps in his case it would be more appropriately titled Whore-ders.

  Two huge television screens projecting graphic porn lit up the otherwise dark bedroom. In the middle, a very pale man was tending to his own business (if you’re catching my thinly veiled innuendo) and puffing on a joint before passing it around to the nearest blonde. The girlfriends, in various stages of undress, were sitting in a semicircle at the edge of the bed—some kneeling, some standing, and some lying down.

  I sat myself on the edge of the bed—unsure of what to do next. I leaned into Vicky—after all, she was the one I was most comfortable with.

  Maybe if I hide behind her, I thought, I’ll go unnoticed for the night.

  “Fake the fuck!” she hissed in my ear and pulled me towards her. “I’ll explain later!”

  She didn’t have to explain. My eyes had adjusted to the darkness and I could see that all the girls, backlit by the large screens, were putting on a show: they were going through the motions as if they were getting it on or making out with each other, but no one really was. It was just a big façade. No one was actually in the mood (besides Hef, I assumed) or turned on in the slightest. Like the porn itself, it was all just for show. There was loud music blaring, but if you got close enough to any of the girls, you could hear them gossiping with one another or making fun of what was going on in front of them. If smartphones had been around then, I’m pretty sure they would have been texting or checking their Instagram when Hef wasn’t looking.

  When I think about it now, it’s almost comical. Every red-blooded American male has no doubt fantasized about what went on in Hugh Hefner’s bedroom with his harem of blond bombshells. The answer? Not a whole lot.

  Looking back, I don’t know if Hef believed the charade. Truthfully, I don’t think he cared one way or the other. Whether it was real or fake, he would be satisfied in knowing that the only reason it was happening at all was for his own personal pleasure.

  The girlfriends, and Vicky, it seemed to me in particular, were desperate to bring as many new girls up into the bedroom as possible. With more “fresh meat” available for Hef, it was less likely that they’d be called on to have sex with their “boyfriend” as often. Hef could keep up with only so many girls in a night, so, as I saw it, Vicky had quickly figured out that recruiting new girls effectively achieved two goals at once: not only would she most likely avoid having to have sex with Hef, but she’d also earn his favor by bringing around pretty new young things for his enjoyment. Of course at the time, I knew none of this. Despite the bimbo label often placed on Hef’s harem, some of these girls were quite savvy. Girlfriend politics was serious business: ruthless, calculated, and complex. On that particular night, Candice and I were the newest victims—and it definitely felt to me that our new “friend” pushed us into the action.

  “Heeeef . . . don’t you want to be with the new girl?” Vicky screamed over the loud music as she reached over and pushed him towards me.

  Much to my surprise, my turn was over just as quickly as it started. By the time I was able to wrap my head around what was happening, Hef had already moved on to Candice, then to a few of his actual girlfriends before finishing off by himself, as he always did. I have never had a more disconnected experience. There was zero intimacy involved. No kissing, nothing. It was so brief that I can’t even recall what it felt like beyond having a heavy body on top of mine.

  Even though it was just a few short minutes of my life, I had never taken intimate experiences lightly, so it weighed heavily on me. I was disappointed in myself that it had come to this. Even in my drunken haze, I knew that it was a big decision I would have to live with.

  Some of the girls leaned over and quickly pecked Hef on the cheek—in the same unattached manner that most would probably kiss their grandfather. The girls began filing out of the room, offering Hef a few candy-coated “good nights.” Quickly, I pulled on my pajamas and followed Vicky down the hall and into her bedroom. I was so wasted that I forgot to grab my club clothes and purse—which were strewn about somewhere on the floor of the master suite. Vicky ordered cheeseburgers and fries to the room as if it were any other night, but I passed out before the food even arrived.

  Over the years, I would see so many girls come and go through that cavernous master bedroom. I never encouraged anyone to come up there and was often downright cold to some of the girls Hef would invite out with us. It wasn’t because I felt threate
ned or even due to my own embarrassment, but mostly because I didn’t want to do to those girls what Vicky had done to me. I had hoped my hard exterior would dissuade them from making my same mistakes. Vicky had tried to act all buddy-buddy, like we were just friends having fun together, like she wanted me to be a part of her club, but I had been used: plain and simple. Unfortunately, it took me a while to realize that. At the time, I wanted to believe that Vicky actually liked me, and only pushed Hef towards me because she wanted me to become a girlfriend. Like I said in the beginning, I was naïve.

  THE FOLLOWING MORNING, I woke up feeling terrible—and it wasn’t just the hangover. Vicky escorted me back to the master bedroom to help me look for my clothes and purse. And just as if it were any other morning, she gave me a friendly hug good-bye.

  But I couldn’t just leave. I had to find Hef.

  After asking one of the butlers where he might be, I finally found him in the library busying himself with notes for that Friday night’s mansion movie screening (before each movie he always prepared a sort of speech).

  “Hef, can I bother you for a second?” I squeaked, my voice breaking midsentence (I would quickly adopt this as my “go-to” pitch when speaking with Hef—the higher octave made it easier for him to hear out of his one good ear). Without even looking up from the pages, he gestured with one hand that I enter his lair. In light of the evening prior, I was even more nervous in his presence than usual. Hef was so used to girls coming in to ask for favors, though, that he didn’t seem at all surprised by my impromptu interruption. I had gone from hoping to move into the mansion to downright determined. There was no way I was not going to get what I wanted after having to sleep with him the night before (or, rather, earlier that morning).

  In the years that would follow, I noticed that after being intimate with Hef, the new girls fell into one of three categories: the hustler, the runner, or the fighter.

  Most of the girls that ended up becoming girlfriends reacted the same way: they were very nonchalant about their “initiation.” Before the sun even rose the following morning, these hustlers were already calculating just how many pennies they could squeeze out of the arrangement.

  Next, we had the runners. While the hustlers were scheming, the runners were fleeing. Like a hit-and-run, these girls would bolt from the scene, never to be heard from again. While most—if not all—had hoped to land a pictorial, they disappeared off the face of the planet, never returning for another night out or party, despite being invited back. The “runners” always seemed like inexperienced girls, so I assumed they didn’t come back because they didn’t like what they had seen or done in Hef’s bedroom while under the influence of alcohol, Quaaludes, or both.

  My reaction fell into the third category: the fighters. I was freaked out and, frankly, ashamed by the experience. After disappointing myself like that, I had to come away with something positive, something to make it right in my mind, somehow. I knew that if I couldn’t find a silver lining, I couldn’t forgive myself for the night before. The other girls who would react as I did were probably the most damaged and affected—we couldn’t so easily shrug off what we had been reduced to. It would haunt us, but in order to move forward we needed to find an upside.

  For me, asking to move in therefore seemed like the next rational step—or so I convinced myself—and I decided to bite the bullet. After all, it hadn’t occurred to me to invite myself out to a club night until prompted—and I had met a very welcoming response—so I figured I might have the same luck with moving in. I was a young blond girl with a small waist and large boobs, but I wasn’t quite as polished as the girls that usually decorated Playboy’s pages—and hallways. Still, for the most part, I fit the bill of “girlfriend.”

  I can do this, I thought.

  It might be hard to understand, but in that moment, I didn’t blame Hef for anything creepy that had gone on the night before. He had the “nice guy” act down pat and it worked. At the time, Hef still had a certain swagger. There was a gentlemanly air about him that belied his reputation. And there was never a shortage of Hef’s friends lingering around the mansion who were all too eager to remind every pretty young thing that stepped through the doorway what an amazing, kind man Hugh Hefner is. It was easy to fall under the spell. If anything, it was the other girls I felt used by, and I couldn’t let them win.

  “Can I ask you something?” I let out another squeak. He looked up at me for the first time and I flat-out told him that I had no place to live. “What do you think about me moving in?”

  He took a brief moment to consider what I had just asked before finally saying, “You can stay for a while and we’ll see how it works out.”

  CHAPTER 3

  “It’s really dreadful,” she muttered to herself, “the way all the creatures argue. It’s enough to drive one crazy!”

  —Lewis Carroll, Alice’s Adventures in Wonderland

  It only took me one trip in my beat-up red Toyota Celica to move my entire life from a tiny Westwood apartment into a Holmby Hills estate. No one offered to move me in, but I didn’t really need the help. I didn’t have much to bring besides the few outfits I owned, some makeup, my college books, and a handful of childish knickknacks, like Disney Princess picture frames and Star Wars figurines. I don’t even think I owned a curling iron at the time. I left my single twin mattress next to a Dumpster.

  As I pulled up the iconic driveway on Charing Cross Road, it couldn’t have felt less like “home.” The gates opened for me, and just like that, I was the newest resident of the Playboy Mansion. I pulled my car through the driveway and gave the keys to one of the staffers, who then made a call to one of Hef’s secretaries. She directed me to my room and presented me with my room key.

  Less than an hour later I had moved my belongings into the bedroom that Hef’s secretary designated for me, and that was that. None of the girls even poked their heads out of their bedrooms, let alone offered to help. I was pointed to my room and left alone. Now what? I thought. It was entirely bizarre.

  I didn’t tell many people about my decision to move into the mansion—I quickly learned that not everyone had the most positive reaction. I had naïvely thought of myself as an adult who was free to make her own decisions, out of high school, away from small-town Oregon, and far from the type of people who would judge me for my personal decisions. I was so wrong.

  When I told Nora I was moving into the Playboy Mansion, her jaw dropped so quickly I thought it would hit the ground. Nora was hyper-materialistic and wasn’t expecting me to go from “rags to riches” faster than her. In my excitement, I also told the first acquaintance I had run into while doing errands. His reaction wasn’t what I had expected, either.

  “You hooked up with an old dude?” he cried, his face scrunching up. “Gross!”

  All I had said was that I was moving in—nothing about being intimate with anyone. I guess not everyone was as naïve as I had been. Seeing the angry look that appeared on my face, he quickly switched gears.

  “So,” he said, his voice much friendlier, “can you get me on the list for the parties?”

  This guy clearly had no shame. Needless to say, I told him no.

  After my friends’ less-than-supportive reaction, I was too terrified to tell anyone else. I was naïve enough to believe that the decisions I made in the relative privacy of that dark cave of a bedroom would remain just that: private. I was by no means prepared for the large scarlet letter that had been branded on my chest.

  I knew my close friends and family wouldn’t approve, but I had already made the decision. Listening to their words of warning and disappointment would only make me feel worse. To be totally honest, I was already ashamed enough and I wanted to delay any further conversations until I had a better understating of what my life would be like.

  Any remaining doubts about my decision vanished when, on an early morning about a week after I had moved in, Vicky stormed into my room screaming: “We’ve been bombed! We’ve been bombed!”<
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  It was September 11, 2001.

  “New York and the Pentagon,” she shrieked. “We’ve been bombed!”

  I hobbled into the bathroom feeling sick to my stomach and paralyzed with fear. I imagined that terrorists had bombs aimed at every major city in America. Were we next? In that instant, I couldn’t have been more grateful to be inside this great big, safe house.

  Of course I soon discovered that we hadn’t actually been bombed: but the reality was no less scary. Terrorists hijacked four American airliners and crashed two of them into the World Trade Center towers in lower Manhattan (as well as one into the Pentagon in Washington, D.C., and one in rural Pennsylvania).

  Thank God I’m here, I thought. I would have been so much more scared had I been out on my own, couch surfing or worse.

  The first few nights I slept in Bedroom 3—one of the biggest guest rooms in the mansion with three beds and a private bathroom, but like all the other guest rooms in the house, relatively plain. Strangely, it also doubled as a bedroom for Hef’s two sons Marston and Cooper (who were 9 and 10, respectively, at the time) if they ever were to spend the night in the mansion. Though they never stayed over while I was there, there were still toys scattered across the bedroom floor—which made for an incredibly odd and, frankly, creepy juxtaposition.

  April was also residing in Bedroom 3, and she intimidated the hell out of me. She was taller and bigger boned than Hef’s usual type and had an in-your-face personality. I had heard she used to be a stripper even though Playboy has a somewhat hypocritical “no stripper” policy when it comes to Hef’s idea of the wholesome Playmate image. She also had a constant need to be the center of attention—and would do whatever she needed to keep the spotlight on her, no matter how raunchy. She also made zero effort to hide the fact that she felt I was intruding on her space.