Down the Rabbit Hole

by Holly Madison

  All of the bedrooms contained mismatched, beat-up furniture. Bedroom 5 had an old wooden dresser tucked into one corner, a small TV mounted on the wall, and a bed so large that there wasn’t much space left to move around the floor. Faded pink curtains covered the small windows that looked out onto four parking spots next to the outdoor kitchen. There was a tiny walk-in closet that housed the few clothing items I owned, plus a black Playboy-brand dress Adrianna had left behind. Clearly, I had a clothing complex and was terrified that I would quickly run out of club-appropriate attire, so finding this little black dress was a huge relief.

  But that wasn’t Adrianna’s only parting gift. She had also worked as a Hawaiian Tropic girl and we had met on a few occasions before she had moved in. While we were by no means close, she made it a point to find me before she left to wish me well. When I asked her why she was choosing to leave, she said, “I don’t really feel like it’s the right thing for me anymore.

  “I know you’re just moving in, but this place can be kind of rough,” Adrianna went on, offering me just a bit of warning. At the time, I wasn’t quite sure what she meant, but I later learned that since she scored a centerfold almost immediately, the other girls were pretty hideous to her.

  My first day in Bedroom 5 was quiet and uneventful. I remember it was a Thursday, which was the only night of the week there was nothing planned on Hef’s agenda. When I asked Vicky if she wouldn’t mind filling me in on the schedule, she acted as if it were some big annoyance. It’s not like anyone handed you a pamphlet when you walked through the door and I was terrified that my “trial period” would come to an abrupt end, so I wanted to make sure I was playing by all the rules. I chalked it up to a bad mood, but she didn’t seem that excited to have me as a neighbor.

  After some coaxing, she finally offered me the rundown:

  • Monday was “Manly Night.” Hef would have his guy friends over for a buffet dinner and a movie in the mansion’s screening room.

  • Tuesday was “Family Night.” Hef’s wife and two sons, who lived next door in a house Hef had purchased for them, would come over to all spend time together.

  • Wednesday and Friday were “Club Nights.” We were all expected to be ready by 10 P.M. to be shuttled off with Hef to exclusive nightclubs all around Los Angeles.

  • Thursday (like Monday and Tuesday) was an “Off Night.” While we had the evenings free to do as we pleased, the girlfriends were still required to be inside mansion walls by 9 P.M.

  • Saturday was a buffet dinner and movie with Hef.

  • Sunday was the “Fun in the Sun” pool party during the day and dinner and a movie at night.

  No one gave me a tour of the mansion when I arrived, either. I knew my way around the grounds and most of the main house, but for weeks I kept discovering new places on the property. There was an underground secret passage that led from the main house to the gym, which was in the basement level of the bathhouse. The mansion itself had a large basement, full of employee lockers, storage closets, and laundry facilities. A panel in the wall of the living room could pop out to reveal a secret wine cellar, which was used as a speakeasy in the 1920s when the house was built. The master bedroom had an attic level where Hef kept a personal office, of sorts. The adjacent bathroom truly looked like a time capsule or the land that time forgot. Gold shag rug covered the floor. A tray of toiletries from the 1970s sat untouched on the counter. The sink handles were carved to look like naked ladies.

  There was a four-bedroom guesthouse on the grounds that hosted Playmates and Playmate candidates when they were brought in from out of town to shoot at Playboy Studio West in Santa Monica. I assumed the Playmate guesthouse would be plush and clean, like a hotel, with perhaps some Playmate memorabilia strewn about to give it a sense of atmosphere. In reality, the guesthouse could have been described as “Grandma’s attic meets rent-by-the-hour motel.” In the ’70s, Hef’s girlfriend Barbi Benton had decorated the guesthouse as a charming early-American cottage, but over the years the theme fell apart. What was left was dark, dingy, and depressing.

  There were many rules to living in the mansion, but most of them I had to figure out on my own. Like I said, no one handed me The Playboy Mansion for Dummies when I arrived. I also learned that the other girlfriends weren’t so eager to help out the newbies, since it was in their best interest for us to stumble around in order to make all of them look better.

  First, there was a curfew. For being an older man, Hef stayed up reasonably late (usually tucking in around 11 P.M.), but he required his girlfriends in by 9 P.M. Apparently, we couldn’t get into too much mischief outside the walls before that hour. I had been present once when Vicky and Lisa had rolled in a half hour past curfew and got a major dressing-down from Hef (no pun intended). He kicked his feet, mustered up some questionable crocodile tears (was he really crying? I thought), and told them that if they wanted to “stay out late” they could move out. Needless to say, his temper tantrum made a lasting impression on me.

  Next, the girlfriends were not allowed to “fraternize” with the staff unless absolutely necessary. This rule was not to be taken lightly. Hef would totally lose it if he caught one of us talking with anybody on the service team (and I eventually witnessed his irrational freak-out firsthand when future girlfriend Kendra Wilkinson spent too much time in the butler’s pantry). According to mansion lore, there were two instances of girls having relations with mansion staffers. First, his ex-wife allegedly had an affair with one of the members of the security team—and Hef found out. Second, one of the girlfriends had supposedly been caught sleeping with a butler. Now, I can’t prove that either of these things happened, but it would explain why he was so overly sensitive about this particular rule. In the beginning, I’m sure the staffers thought I was terribly aloof and cold, but I was honestly just scared shitless. If I got kicked out, I had nowhere to go. I couldn’t risk it.

  Each girlfriend was given a weekly “clothing allowance” of $1,000 for expenses. It was expected that we use this money to purchase clothing to wear for evening events as well as beauty treatments (hair, nails, waxing, etc.) that weren’t covered by his in-house account at José Eber Salon in Beverly Hills. This was a welcome relief for me. It was clear that Hef preferred we dress in a particular way when we were out on the town with him, and I was desperate to revamp my wardrobe and fast! Hef made it abundantly clear that he preferred us in very over-the-top, sort of trashy outfits (think BeDazzled rhinestone bustiers and skirts so short there was barely a point in wearing them). When he would compliment a girl on a particular dress, pair of shoes, or even the way she wore her hair, we all felt the need to replicate it for our next evening out.

  The last major requirement was that girlfriends attend the events designated on Wednesdays, Fridays, Saturdays, and Sundays. While the girlfriends were always eager to party at the hottest Hollywood nightclubs on Wednesdays and Fridays, it was clear they used whatever excuse they could to get out of “dinner and a movie” nights. Oftentimes, it would just be April and me flanking Hef at the main dining table. We were still the two newest girls, so paying our dues was part of the program. The other girls stayed out until 9 P.M. on the nose, not wanting to miss even a single minute of freedom—which usually meant visiting the boyfriends that they kept on the side.

  How these “side boyfriends” felt about their girlfriends dating Hugh Hefner, I don’t know. I imagine the girls weren’t forthcoming with these men and probably denied that they even had sex with Hef (they denied it to everyone). Most of them referred to “dating” Hef as a big publicity stunt to help them launch their careers. Maybe some of the guys got a perverted little kick out of the fact that they were dating the same girl as Hugh Hefner. Who knows?

  Contrary to popular belief, most nights at the mansion were pretty boring. We usually ended up in one of the bedrooms gossiping or watching TV. One night Lisa was hanging out in Vicky’s room and the doors to our connecting bathrooms were open. When Tina came to visit, I went
into Vicky’s room to try and make an effort to be friendly with the girls. Tina was excitedly talking about her “boyfriend,” and like the socially awkward person I was, I asked her, “Do you feel like he even takes you seriously when you live with Hef?”

  My intention wasn’t to be mean; I actually wanted these girls to like me! I was genuinely curious. When I shared the news that I’d be moving into the mansion, I hadn’t met the warmest response, so I wondered how everyone else’s friends, families, and even boyfriends felt about it.

  Tina whipped her head in my direction and snapped a dismissive response at me. I grimaced and tried to apologize, but Tina wouldn’t even look at me. She just rolled her eyes at Vicky.

  As you could have predicted, Tina’s boyfriend didn’t stick around long. In fact, none of the “side boyfriends” ever stayed longer than a few months at most. I don’t think the men took them seriously. I always assumed most men were just using the girls to check some Playboy Bunny fantasy off their bucket list. I only ever saw one “side boyfriend” stick around: Hank Baskett.

  Following the rules wasn’t difficult for me. I didn’t know too many people in Los Angeles and I quickly cut out the small group of friends I did have—either because I didn’t want to be subjected to their judgment or because they started to call asking for invites to the mansion and other favors I couldn’t grant. Plus, I’ve always been a bit of a homebody and much preferred the delicious home-cooked meals the staff provided to dancing the night away at nightclubs (where I would usually get pretty drunk purely out of sheer boredom). Most of the girls would have rather died than sit around the dining table with men three times their age, but I found Hef’s friends funny and interesting, and genuinely enjoyed listening to all of their stories. Eventually, I would convince myself that this was yet another component of the common ground Hef and I shared as a couple.

  Usually the movie nights included a steady rotation of Hef’s favorite classic films and I adore old movies—something we were truly starting to bond over. Every Sunday night, Hef’s office would arrange to have studios bring in movies that were still in theaters—and armed guards would enter the mansion with giant film cans to screen the newest Hollywood blockbuster for us. It was pretty cool, but it also was sort of bizarre, because oftentimes celebrities or other important Hollywood power players would join us for the screenings and be relegated to spending roughly two hours squirming in uncomfortable metal folding chairs. For being a super upscale home, it wasn’t without its downscale touches. One of the most memorable was the tray of Johnson’s Baby Oil, Vaseline, and Kleenex that was in every bathroom, in the grotto, and at the tennis courts and the pool bar. I still don’t know whether to be disgusted or amused by those trays.

  At first, my constant attendance at all of the events deemed “boring” by the other girls earned me a bit of good grace with them. They felt that I took some of the attention off their recurring absences while they busied about with their outside lives. Girls would find crafty ways to sneak out past curfew when they thought it wouldn’t be noticed—like hiding in the trunk of someone’s car as they drove off and onto the property!

  While evenings at the mansion were pretty regimented, during the day we were virtually free to do as we pleased. Hef was usually awake by 10 A.M. for breakfast, then meandered down the hall to his office wing, where he would work on the magazine, various book projects, and other business. He wouldn’t emerge again until the evening.

  In the beginning, I spent most days with Britney—a nice girl that I had met at the Sunday pool parties. We’d go to the gym, tan, lay by the pool, and cruise around L.A. searching for bargain clothes. The only other girl I remember spending time with was Lisa.

  Besides me, Lisa was the youngest girlfriend in the group at that time. She lived in Bedroom 2, the largest of the bedrooms, and was still celebrating the release of the issue in which she was the centerfold. She was a cute country girl who, according to the other girls, dated Kid Rock on the side, though I never saw any evidence of it. She had first auditioned for Playboy over a year prior to her Playmate pictorial finally being published. Somewhere along the way, she met Hef, became a girlfriend, and secured a centerfold after acquiring a new set of Hef-financed breast implants to lift the mammaries that he’d deemed “too droopy” for a Playmate.

  Like most of the other girlfriends, she was both manipulative and manipulated. Becoming a published centerfold didn’t happen overnight. In fact, Playmate features were often shot 8 to 12 months before they actually hit newsstands. According to Vicky, Lisa had been a girlfriend for several months before losing patience.

  “She threw a fit when we were out one night, asking when she was going to finally shoot her centerfold,” Vicky once explained to me, rolling her eyes and exhaling cigarette smoke. “She’s the baby, she always gets what she wants.”

  “This is like a boy band,” my friend Britney added. “Hef has to have an old one, a young one, a wild one . . .”

  This brought a cackle out of Vicky, who rolled her eyes.

  “He always plays the oldest one against the youngest one,” Vicky explained, eager to share her expertise on the topic as we gossiped about the situation. “Tina may be his main girlfriend, but she’s older, so he likes to play on her insecurities by playing favorites with whoever the youngest one is. And Lisa isn’t special. Before her, he used Buffy to play against Tina.”

  I took note of this, but at the time I didn’t want to believe a man as old and accomplished as Hef could be that petty and immature. Vicky was starting to show her nasty side, so I wrote it off as jealousy on her part.

  Lisa was one of the friendlier girlfriends. In fact, when I walked by her room one morning, she called me in.

  “Hey, wanna go to Target with me later? I need to run some errands.”

  “Yeah, sure, lemme know what time!” I said, feeling lucky to be invited. I was hoping she could fill me in a little more on how things worked around the mansion, since Vicky and the others had given me the cold shoulder.

  “Ugh. I need to get lipo,” Lisa croaked, looking down at her belly and pinching her spare tire. She was adorable, but had been told to lose weight by a Playboy photo editor.

  “No you don’t,” I said. “You look fine.”

  “Thanks!” she replied through a toothy grin.

  As I knelt down to pet one of her three dogs, she picked up the phone next to her bed, pressed 0 for the butler’s pantry, and ordered a piece of chocolate cake and a glass of chocolate milk for breakfast. Was I in the twilight zone? Plastic surgery was so commonplace for these women that liposuction sprung to mind as the obvious weight loss cure before, say, taking chocolate cake out of your breakfast routine.

  “Hang out here while I get ready,” Lisa demanded while hopping into the bathroom. After she had chattered on about herself for about 10 minutes, her cake was finally delivered. She thanked the butler, plopped the tray down on her bed, started shoveling the cake in her mouth, and asked, “So, how do you like it here so far?”

  Finally, someone I can talk to! I thought with relief. Now was a good time to ask a few questions and confess a few of my insecurities about this wild world I had just entered. I confided in Lisa that I wasn’t too fond of April, that she really intimidated me.

  “That’s okay, the rest of us don’t like her, either,” Lisa stated, wrinkling up her nose. “Hef just likes her because she’s wild.”

  “Oh, wow, thank God it’s not just me!” I sighed, feeling relieved. Maybe April wouldn’t last that long and then we could all really be like sorority sisters; all on the same team.

  Feeling more and more comfortable with Lisa, I thought I would ask her opinion about something that had started worrying me the past few days.

  “Hef hasn’t given me a bunny necklace yet,” I admitted meekly. “Do you think that’s weird?”

  Every Playmate and every girlfriend was presented with a bunny pendant necklace from Hef. At the time, I (along with everyone else in L.A.’s 30-mile z
one) thought these necklaces were made with real diamonds. They had looked so glamorous, glittering on the chests of the chosen ones who flitted about the Playboy parties, the hottest nightclubs, and the spendiest shopping districts in L.A. (In reality, the pendants were cubic zirconia, and if you could track down the Downtown L.A. jeweler who made them, anyone could purchase one for just $100.)

  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.