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

by Holly Madison

  My interest in acquiring a necklace had nothing to do with its value, however. Sure, I coveted one, but my worry stemmed from what it symbolized.

  Hef’s words echoed in my mind: “You can stay for a while and we’ll see how it works out.” Maybe I wasn’t making the cut. That had to be why he hadn’t graced me with a necklace yet. In the few weeks I had been there, he had presented one to Charis Boyle, an upcoming centerfold, whom he had met after me. Somehow I had been skipped over.

  “Oh, he hasn’t?” Lisa asked, feigning amazement. “Ohhhh. Yeah, I dunno why that is.” She purred as she put down her fork and sauntered back into the bathroom.

  I felt a knot form in my stomach. That was definitely not the reaction I had hoped for. Lisa’s sisterly vibe had me hoping she would reassure me that this was normal or perhaps even offer to ask for me—after all, she seemed so comfortable around Hef and was certainly good at getting whatever she wanted.

  As Lisa readied herself for the day and led me down to her car, my mind was in turmoil. Was my time here almost over? I had barely been at the mansion two weeks and already I didn’t seem to be making the cut. What would I do now?

  As it turns out, I wasn’t the only one with these kinds of anxieties.

  As we wound our way through L.A. traffic down to Target in Culver City, Lisa kept babbling about herself. I found her stream-of-consciousness narrative fascinating, as her anxieties mirrored mine. The only difference was that she had been here longer and had a centerfold under her belt.

  “See this?” she bragged, holding up her checkbook for me to see the balance, which hovered just above $25,000.

  “It’s the money I earned doing my Playmate pictorial!” she exclaimed proudly. “I haven’t touched a penny! You know, the other girls aren’t even thinking. They have Hef leasing them cars they could never afford and they spend money like there’s no tomorrow.”

  She looked pleased with herself.

  “Everyone made fun of me for getting this car,” she said, patting the steering wheel of her brand-new Toyota RAV4. “But I want something I can afford after I move out. I don’t need a Porsche.”

  Smart, I thought. In fact, it was the first sensible thing I had heard out of any of the girlfriends’ mouths so far.

  As we roamed through Target, she filled her shopping cart with everything from a nose hair trimmer to dog toys. “I always spend so much at Target,” she sighed. “You always walk out of here with more than you need.”

  I smiled and nodded my head in agreement. Before another pause could pass, Lisa started babbling again.

  “You know, I don’t know if I could ever go back home,” Lisa continued. “One of my guy friends from home, the other day he got real rude with me on the phone and said the only reason I got centerfold was because I fucked Hef.”

  I wasn’t 100 percent sure if she was even talking to me anymore—or just thinking out loud.

  She shrugged her shoulders and tried to offer a halfhearted smirk, but I could tell the comment bothered her deeply. I could certainly relate. Like me, I think she got into this situation without quite realizing what a public decision it was.

  “It’s not true. You’re gorgeous,” I offered, trying to cheer her up. “You could have become a centerfold anyway.” And it was true. She was curvy, cute, and baby-faced, resembling a petite version of Anna Nicole Smith.

  “Thanks,” she sighed, offering a weak smile. “But I can’t go back home. I mean, what am I supposed to do? I’m not above working a real job, but, like, if I’m working at a counter somewhere everyone I know is gonna come up and be like ‘ohhhhh, Lisa, look where you are now after posing naked.’ It’s embarrassing.”

  I was just as anxious as Lisa was about the life that waited for me outside the mansion gates. So many things seemed to be grounds for dismissal that I was petrified to step out of line. While becoming an actress was still a passion of mine, it was always best to keep any auditions quiet. After Brande Roderick had left Hef for Baywatch Hawaii, he kept a much closer eye on any acting work the girlfriends tried to pursue. I secretly hoped to land a role big enough that it would allow me to leave the mansion after a few months, but those kinds of dream jobs are few and far between. Eventually I would receive offers for smaller parts in music videos and low-budget films—but the hours often went past our curfew and the jobs rarely paid much, so they hardly seemed worth it. If anything, they would only land me in hot water with my boyfriend who, as the weeks passed into months, appeared more and more controlling. It seemed my acting dreams were stalled for the time being. I felt caught between a rock and a hard place. I thought having a rent-free roof over my head would make chasing my dreams so much easier, but that wasn’t turning out to be the case.

  I had managed to hold on to my day shifts at Hooters for a few months—I guess Hef didn’t feel particularly threatened by a lowly waitressing job—and I was able to slowly start paying off the debt I had amassed in college. It wasn’t much, but it was a start. As they do every year, Hooters chooses a waitress from each region to be featured in the Hooters magazine and participate in their national bikini contest. One day, the general manager called me into her office and told me that Hooters wanted me to represent Santa Monica.

  I was very flattered. There were so many beautiful girls that worked at the restaurant and they had chosen me! My friend Roxy had been chosen the year before and had told me how much fun it was and how many people she had met. I was still hoping to break into the entertainment world and was eager to take any opportunity—even if it was just a pageant title.

  “No,” Hef said when I told him about the offer and asked permission to leave for two days. I expected him to maybe pout a bit, but I wasn’t really anticipating a flat-out no. Hef never seemed bothered by my job, and since he wasn’t eager to feature me in Playboy, I couldn’t imagine why he would care about me being in another magazine, especially since there was never anything racier than a bikini photo in the Hooters magazine.

  “You can’t do it,” he shouted, pounding his fists on his desk. His voice had become irrationally loud.

  “Why?” I asked. I had already agreed to do it and was totally perplexed by the strange tantrum he was throwing.

  “Because you working there makes me jealous,” he yelled, his hands flying in the air, doing his best to well up some more fake tears.

  In the months I worked at Hooters, Hef never once expressed feeling threatened by my being there. But now that I was getting an offer to do something fun, something that made me feel special, he all of a sudden had an issue with it? The timing was a little too convenient.

  Hef was waiting for me to argue or to cry, but I just stood silently in front of his desk. I could see the anxiety creep across his face; he didn’t know how to read my nonreaction, so he took it a step further: “I don’t want you working there while you’re living in this house,” he shouted, hoping this would evoke some response. He thrived on this kind of drama; he was half hoping for me to surrender and half hoping for a fight.

  Without saying a word and as stoically as possible, I turned around and saw myself out of his office. Inside, I was crushed, but I was trying to keep my dignity.

  The next day, with a heavy heart, I called the general manager and let her know that not only could I not attend the pageant, I was quitting my job as well. Honestly, I can’t even remember what I said. It was a crushing defeat—and it felt like I was saying good-bye to a part of me. In hindsight, that incident should have been a blaring indicator of what my life was going to be like behind those gates, but I still had high hopes.

  I felt like my last shred of independence was gone. But at that point, I thought I’d seen the worst of it. It wasn’t an ideal world, but I could make it work. I could find some happiness here while I figured out my next move, I reasoned with myself. After all, it would only be a few months, maybe a year . . . at most.

  CHAPTER 4

  “Now, here, you see, it takes all the running you can do, to keep in the same
place. If you want to get somewhere else, you must run at least twice as fast as that!”

  —Lewis Carroll, Through the Looking-Glass

  You girls are basically Hef’s traveling harem, right?” asked the eager New York magazine reporter, sticking a small silver voice recorder in my face.

  Only a few weeks after I had moved into the mansion, Hef whisked us away on a trip to New York City for his Comedy Central’s Friars Club Roast. I’d never been to New York before; I’d actually never been off the West Coast before. It seemed so surreal—and slightly absurd—that a reporter would be questioning me about my life with Hugh Hefner.

  “Umm,” I began, through a short laugh. I wasn’t quite sure how to respond to this older, bespectacled journalist with the practical brown bob. Despite what the nature of the event may suggest, I couldn’t be certain if she was joking or not.

  This particular roast had special meaning to New Yorkers. In the wake of the September 11 tragedy, a dark cloud hovered over New York—and the entire country for that matter. Comedy Central reasoned that giving people an hour of time to laugh again might help kick-start the healing process, and they decided to move forward with Hef’s scheduled roast.

  The day before the event, Hef, his girlfriends, and his staff (including his longtime assistant Mary O’Connor, his personal photographer, and a team of security) boarded a chartered private jet at Van Nuys airport and headed to New York. The network hosted us at the New York Hilton Midtown. Hef and Tina occupied the hotel’s regal presidential suite while the rest of us were given gorgeous rooms with breathtaking views of the city.

  Whose life was I living? Private jets! Luxury hotels! Last month I was barely making rent on a shitty shared apartment. There were many perks to being one of Hugh Hefner’s girlfriends, including the VIP treatment everywhere we went. I’ll be honest, being treated like royalty wasn’t necessarily a hard routine to fall into. Sure, it was mainly directed at Hef and we were considered ornamental, but reaping the benefits of his celebrity certainly had its moments.

  Prior to the festivities, Hef was expected to walk the red carpet with his seven girlfriends for brief press interviews and to pose for photographers. The attire was black tie, so each girlfriend packed her most glamorous cocktail dress or pantsuit. With my clothing allowance I was able to buy a retro style Betsey Johnson black and white ball gown. I loved it, but I felt a little out of place after I realized how conservative my poufy, below-the-knee dress looked next to the other girls’ tighter and more revealing ensembles.

  When we arrived in our stretch limo to the Waldorf Astoria hotel, my heart fell into my stomach. I’d never been to an event like this in my life—let alone on the arm of the guest of honor.

  As we piled on each side of Hef for photographs outside the ballroom, I began shadowing the other girlfriends. Terrified to make any kind of noticeable mistake, I mimicked the girls who appeared to be veterans at this point. Like the other six, I plastered on my brightest smile and stood patiently behind Hef as he conducted one interview after the other. I had to watch my step, though. Simply falling into place in line didn’t work for the other girls. One girlfriend, Carolyn, shamelessly shoved me out of the way so she could stand closer to Hef. (Because we were in front of the press, all of sudden, being as close as possible to Hef was really important to all of the girls, who normally couldn’t be farther away.)

  When the New York magazine reporter shoved her device under my nose, I was taken off guard. I didn’t want to seem unfriendly or rude, so I answered her questions as politely as possible and excused myself to follow the rest of the girlfriends into the ballroom.

  “What did that reporter ask you?” Vicky hissed as I sat down at the large banquet table closest to the stage.

  “She asked me if we were a harem that travels with Hef.” I let out a small laugh. To me, it was just a silly sounding question.

  “What did you say?” Vicky asked me, her eyes like slits.

  “I just sort of laughed and said, ‘Well, I guess so,’ ” I told her, a smile still stuck on my face, completely unaware that I might have done something wrong. I didn’t take the question literally. When she said “harem,” I just thought she meant an ornamental group of women, not sex slaves. I had been around only a few weeks, how was I supposed to know how to answer a question like that? I’d never spoken to a reporter in my life!

  “No,” Vicky spat at me, exasperated. “Don’t ever say that we sleep with him. We always tell people that only Tina does that.” I could see that I rattled her pretty hard. As Hef took his throne on stage, Vicky spent the rest of the evening ignoring me and whispering to the other girlfriends in between venomous glances. She’d clearly misled me in the beginning; I guess I shouldn’t have been so shocked that she was trying to mislead others, too. But exactly who did she think she was fooling?

  The irony wasn’t at all lost on me that the entirety of the evening consisted of sex jokes implying that Hef was intimate with each of the seven blondes sitting at his feet.

  “I’ve read just about every issue of Playboy since I was 15 years old,” began the host, Jimmy Kimmel, “And not once did I see a Playmate say that one of her turn-ons was fucking a 75-year-old man.”

  INSIDE THE MANSION, LIFE wasn’t at all like what I dreamed it would be. Instead of a nightly slumber party with six of your best friends, I had entered the lion’s den. It gave a whole new meaning to the phrase “keep your enemies close” and made a sorority house look like Bible study.

  By the time I had arrived, fewer and fewer opportunities were being offered to girlfriends to appear in the magazine—which meant the pack was getting restless. Over the years, Hef had become wiser to the girls’ true motivations. After achieving Playmate status, they no longer found it necessary to stay at the mansion—or with Hef.

  The truly gilded age of Playboy had long since passed and our nightly rituals felt more Golden Girls than Playboy Club. Girls stuck around on the off chance that they’d one day become a Playmate (or until a better option came along), and Hef knew it. He decided he wasn’t going to make any more of his girlfriends Playmates, but he never told that to anyone. He dangled the possibility of Playmate-hood in order to keep the girls interested. The more aggressive girlfriends would take whatever measures necessary to secure a centerfold, even ruthlessly throwing another girl under the bus if that meant she would gain favor with him.

  As always, Vicky was eager to bring as many girls up into the bedroom as possible. I could guess her reasoning: the more options Hef had, the less likely she’d be called to duty. It seemed to me that she made it her mission to lure every new Playmate up to the bedroom to pay their dues. In those first few years, I would say the majority of the Playmates eventually selected had found their way into Hef’s bedroom. I guess Vicky figured that if she had to sleep with Hef, they all should have to sleep with him.

  I was too naïve to realize it at the time, but Hef was the catalyst for all the drama I was to experience at the mansion. He recognized that some of the girls were warming up to me and began using my perfect attendance as one of his many tools to manipulate and control his wild pack. Pitting the girlfriends against one another created an aggressive, competitive atmosphere where he alone benefited. During one of my first nights at the mansion, the girlfriends had banded together on a Friday evening and told Hef they didn’t feel like going out that night. I was the newest member of the crew, so I just sat there, observing the confrontation.

  “So . . . what do I say to my Party Posse?” he said, throwing up his hands and wearing the most disappointed look ever on his face.

  “Sorry, Hef,” Lisa said. “We’ll go out next week.”

  Needless to say, Hef decided then and there that the girlfriends’ days of being chummy were over. After all, he couldn’t be outnumbered, could he?

  It was in his best interest to have us wallowing in our own insecurities and pawing for his acceptance. Girlfriends that didn’t get along gave him the feeling of being fought over�
��and being fought over made him feel desired, something he was desperate to feel in his old age. A stable environment among the girlfriends wasn’t much fun for him, so he began using me as a means to reprimand them.

  “Why can’t you just be a good girl like Holly?” Hef bemoaned to a girlfriend who wanted a curfew extension, knowing full well that his small remark would pin a bull’s-eye on my back for weeks. They began resenting me for the very reason they initially accepted me.

  A few weeks into my residency, it was obvious that Vicky was regretting the role she played in recruiting me into the fold. Initially, Vicky must have thought that she could use what little relationship I had with Adrianna to her advantage. Hef was totally smitten with Adrianna—who looked like a perfect, fresh-faced beach bunny—so Vicky, who was as mean as a snake, must have thought that I would have some useful information she could use to help take her competition down. Since Adrianna had moved out of the mansion, it was clear to me that my presence was no longer of use to Vicky. I think she continued to deal with me because she considered me average looking compared to the rest of the girlfriends. (They all tried the best they could to re-create that ideal of Pamela Anderson—I on the other hand wasn’t interested in transforming myself into a Spearmint Rhino version of the Baywatch beauty. I wanted to look good enough to be a Playmate, but still hold on to some of what made me unique—and, frankly, avoid looking like a blow-up doll.) But as soon as Hef started using me as a behavioral example, Vicky no longer wanted anything to do with me.