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

by Holly Madison

  It was known that if a girlfriend did choose to undergo some sort of plastic surgery, Hef would foot the bill. The most popular procedures among the girlfriends were breast augmentations (both new and redone), rhinoplasty, and liposuction. Eventually, I would ask for my own nose job, but that was only part of my Playboy makeover.

  During my first few months at the mansion, I was still a college-aged girl who actually liked herself. Without school and work, I quickly became bored and filled my days with activities typical of a 22-year-old girl: shopping, working out, getting my belly button pierced, things like that. One day, my friend Britney and I decided to go get tattoos. I got a small Playboy Bunny tattooed in the middle of my lower back (talk about a tramp stamp!), because I thought it was a cute, fun way to commemorate this crazy experience. This was back when I thought my mansion stay was going to be a short-lived stepping-stone that would soon lead me to something bigger.

  At the time, my only real beauty routine consisted of bleaching my own roots with Clairol ultra-blue from the drugstore. One day, as I was performing the ritual in my bedroom with the door open, one of the girlfriends popped her head in.

  “What are you doing?” she snarled, with a scrunched nose.

  “Dying my hair,” I said, defensively. What did it look like I was doing? I knew these wannabe Beverly Hills bitches looked down on anything do-it-yourself. “I need to save money. I can’t spend it all at the salon.”

  I actually hadn’t been to a salon in my life.

  “Ohhhh,” she cooed maliciously, a smirk slowly spreading across her face. “That’s smart.” She laughed and sauntered down the hall.

  What she failed to tell me was that Hef had an open tab at the José Eber Salon in Beverly Hills, and all the girlfriends had their hair and nails professionally done there several times a week. None of the girls had bothered to share this piece of information with me, because keeping me as homely as possible was in their best interests.

  Finally, I found out about the salon privileges when Vicky had lost patience with me using the strong-smelling dye in our shared bathroom.

  “You know you don’t have to do your own hair, right?” she finally snapped.

  When I arrived at the José Eber Salon, it was like arriving in a whole new world. The staff whisked me into the salon and immediately changed my bright gold hair into the light platinum blond Hef loved. They straightened my naturally frizzy mane and planted long acrylic nails on top of my short ones.

  Meanwhile, months of utilizing the mansion’s gym and tanning beds had taken about 10 pounds off my figure and bronzed my skin into a smooth, perfect tan. Hef’s dentist had given me a bleaching kit for my teeth, which gave my smile a perfect bright Hollywood glow.

  The pictures we received the morning after each of our club nights out provided me with countless opportunities to study how I photographed. I quickly set about honing my makeup skills (which were virtually nonexistent before the mansion). During my first few months there, I don’t think I wore much besides powder and maybe a little mascara. Compared to the Playmates’ carefully contoured faces, my sparse and natural look wasn’t cutting it. My work-free days gave me hours and hours to shop for and experiment with makeup. I learned how to make my lips look bigger, my eyes more catlike, and my eyebrows fuller and more defined. I felt like I was finally beginning to look like the glamorous Playmate I had always wanted to be!

  Staring at my photos, though, I knew there was one last thing to fix. I’d never really been fond of my nose—it was a little too big for my taste, but I rarely thought about it. It wasn’t until I started seeing countless pictures of myself day after day that I realized it photographed even bigger than it was. I compared myself with the Playmates in our group photos—most of whom had tiny, unnoticeable noses. Hef’s favorite girls had “baby faces” with upturned snub noses. I started to feel like it was about time I did something about it.

  While plastic surgery was a common request among the girlfriends, I was still terrified to discuss the idea with Hef. I was uncomfortable enough with my current living situation, so the last thing I wanted to do was ask for anything more. I already felt like enough of a hooker—I didn’t need to fan the flame. Eventually, though, I caved.

  All the other girls get procedures, I told myself. It’s only fair that I should be able to get one, too.

  I took a deep breath and approached Hef. I had spent time doing my research and decided to enlist the help of the same doctor who had performed a nose job on one of Hef’s former girlfriends—a surgery so successful that Hef said he’d “never seen such a transformation before.” After dinner one night, I nervously brought the quote from the plastic surgeon to his room and shakily explained that I wanted to get my nose fixed. He gave me an obligatory two-minute speech about how I didn’t need the surgery, but quickly approved it despite his short-lived chivalry.

  It felt like a victory at the time, but I now recognize that it was one of those watershed moments in life. Sure, my new nose gave me a temporary surge of self-confidence (and I was absolutely thrilled with the results), but it wasn’t my appearance that was in need of immediate attention.

  In a few short months, I had gone from a friendly, optimistic, confident woman to a confused girl with a nervous stammer who second-guessed every thought that went through her head and rationalized every bad decision she made. I was so focused on “making it” and turning this bad decision I had made into something positive that I couldn’t see that all I was really doing was running faster and faster in circles trying to please Hef and simply stay afloat in his twisted world. I had no time or energy left to chase my dreams.

  By this point, Tina Jordan had moved out and Hef had promoted me to his “main” girlfriend. One might think this would offer me some kind of protection from the “Mean Girls,” but no such luck.

  Actually, the other girlfriends all but shoved me into the number one slot. As Hef’s main girlfriend, you were under the microscope. The “Mean Girls” reveled in their lives outside the mansion and didn’t want the extra responsibility where Hef was concerned. Unlike the other girls, I didn’t mind most of the rules. I didn’t have an outside boyfriend and I wasn’t crazy about clubbing, so I didn’t mind the 9 P.M. curfew. The “Mean Girls” viewed it as a win-win. If I was ever present as the main girlfriend, their lack of perfect attendance wouldn’t be as heavily scrutinized, but I wasn’t “hot” enough to be any kind of real competition for the limited Playmate of the Month spots. If they were ever asked why Hef preferred homely little old me best, I’m sure they would lie and say it was because I was the only one who slept with him . . . just like they had all said about Tina.

  Despite the presumed prestige in its title, there was nothing ceremonious about becoming Hef’s number one girlfriend. After Tina’s centerfold was published and she announced her departure, Hef simply asked me if I wanted to move into his room. That was sort of it. No promises were made; no piece of token jewelry was given. I simply prepared to pack up my things and move them down the hall . . . but not before Tina took the opportunity to remind me who was boss.

  Just as I was beginning to move to Hef’s room, Tina dropped another bomb. She announced that she had decided not to move out after all. The other girls didn’t even try to hide their smirks as she shared this news with me (in front of everyone). It was clear I was the only one left out of this loop. My face burned red with embarrassment.

  “So, you can just quit packing up your things,” Tina said in her fake singsong voice as she picked up her purse and followed an oblivious-acting Hef out to the limo. I was hurt and embarrassed, but the subject was never broached again that night, so I just pretended the whole thing never happened.

  Over the next few weeks, Tina would show up halfway through movie nights only to shove me out of the way so she could sit next to Hef. She did the same thing with buffet dinners and would make a huge show out of forcing me to move my chair over so she could sit by Hef.

  I’m not sure if Tina w
as trying to make an impression on Hef so that he would be more likely to give her Playmate of the Year or if she simply had that much fun torturing me. Eventually, though, the novelty wore off and Tina left for good.

  Being tossed back and forth like a useless rag doll by the man I had come to look to for approval did a massive number on my self-esteem. When I finally made the official transition into Hef’s master suite, it felt anticlimactic. I was actually moving all of my belongings from a normal-sized bedroom into a tiny corner of Hef’s closet called “the Vanity.” These cramped living quarters—without even a speck of privacy—was another reason none of the other girls were clamoring for the title of “girlfriend number one.” The back area of Hef’s closet contained a vanity, an island dresser, and closet space lining the walls. There was just enough room to walk between the island and the vanity, but that’s it. In what looked like a castle’s tower from the outside, the vanity had a few thin windows that looked out over the driveway. A musty rose-colored chair and a nightstand with a small box TV were wedged in front of the windows.

  I later talked Hef into installing a desk in place of the TV and chair and putting down beautiful hardwood floors in place of the white carpet, which had long ago been ruined by dogs and Lord knows what else. I had a hard time believing that an elegant man like Hef (or so I assumed) preferred the nasty old carpet to the classic hardwood floors that so complemented the rest of the room. I was wrong. Instead, Hef insisted the change was a huge sacrifice he made for me and that “if this doesn’t show you how serious I am about you, nothing will.”

  Did he really just suggest that his love for me was reflected by his willingness to rip up decades-old carpet? I thought. Yes, yes, he did.

  Speaking of declarations of love, now that I was Hef’s number one girlfriend, the vows of love flowed freely, just as they had to Tina days earlier. “I love you” was something he said often and to anyone he was even remotely involved with, including me on what was our second night out together. I realized that was abnormal, but I came to hope that those feelings were true, particularly as he started referring to me in front of friends as the “love of his life” and telling the press he expected to spend the rest of his life with me. That last quote quickly turned into a punch line as late-night comedians speculated if the “rest of his life” meant one or two more years.

  I suppose the main girlfriend role did have some other “perks.” Suddenly, Playmates who had once mocked me were kissing my ass, bringing me gifts, and showering me with compliments now that I was Hef’s number one girlfriend. The sudden shift in the way some of those girls acted was completely obvious and shameless, but I suppose they thought I was too dumb to notice or that I would be so grateful to be treated kindly for a change that I wouldn’t object. The reality was, I knew I had to choose my battles wisely. I graciously accepted their gifts and their compliments, but I wasn’t stupid and I never forgot how they had treated me before, when I was just the lowest blonde on the totem pole.

  Despite being on the receiving end of Hef’s romantic declarations and suddenly being “popular” with the Playmates, I still wasn’t exempt from Hef’s harsh criticisms. Among the many unspoken rules at the mansion, the red lipstick rule was one of the more notorious. Hef hated red lipstick. It was one of the few helpful hints I managed to squeeze out of Vicky. I’m not overexaggerating here; Hef absolutely despised red lipstick and wouldn’t allow his girlfriends to wear the color.

  “Maybe he doesn’t want lipstick on his collar,” Vicky had suggested years earlier. I always found it so hard to believe, because Hef has such a deep appreciation for the gorgeous film stars of the golden age of Hollywood. Betty Grable, Alice Faye, and his muse, Marilyn Monroe, were always painted with succulent red lips. It didn’t make any sense that he wouldn’t want his girlfriends to exude that same kind of glamour, so I didn’t take her warning too seriously.

  I would learn my lesson the hard way.

  About six months after moving into the mansion, I felt ready for another makeover. I loved my waist-length thick, natural hair. In fact it had long been the physical attribute I was most proud of—mainly because it was the only thing I had that all the other girlfriends, with their extensions and clip-in locks, had to buy. New girls were always coming through the mansion’s revolving front door, but I was the only one with enviable hair.

  Until Mary Jo. She was a southern belle flown out from Alabama for a Playmate “test shoot.” She had ass-length blond all-natural hair and was dead-set on becoming Hef’s newest girlfriend. This woman wasn’t just any old blonde; she was single-handedly hijacking the only thing that made me different. I couldn’t believe how threatened I felt by her. The fact that I could be so easily upset by something like this made me want to rebel, to do something that would make me an individual, so that I wouldn’t constantly feel so replaceable.

  I was cracking under the pressures of living at the mansion and resented the fact that everyone had to look like such a clone. Save for the blond hair, the big boobs, and our shared address, I had absolutely nothing in common with these girls. So why should we have to look like we were carbon copies of one another?

  I decided to take it upon myself to embrace a more retro aesthetic—a look that captured the old Hollywood glamour I was so fascinated with. Think: more Marilyn, less Pamela.

  One sunny afternoon, I decided to do the unthinkable: chop off all my hair. I drove directly to the hair salon and instructed my stylist to cut off about 20 inches of platinum blond hair. It was a drastic move, but I felt liberated by my short new coif. While all the girls were in a race to see who could have the longest hair possible, I had a flirty chin-length bob. I completed the look by having the hairdresser and makeup artist style me like Marilyn Monroe. Though I was making the change for me, I was also sure that Hef wouldn’t mind. After all, he worshipped Marilyn and often cited her as the ideal in feminine beauty.

  When I got back to the mansion, complete with curled bob, black eyeliner, and red lips, I sat down at my vanity. This is a fun look, I thought, admiring my new reflection as I heard Hef shuffle into the bedroom.

  “Come in here, Puffin,” I said in a happy singsong voice, “I want to show you something!” I stood up and straightened out my white Juicy Couture jumpsuit when he finally appeared in the doorway.

  “What did you do?” he spat at me. Instantly, I was taken aback.

  “I got a little makeover,” I said sheepishly, giving a slight pat to my new hair. Any shred of confidence I found over the last few hours was quickly evaporating. “I thought you would like it.”

  “Well, I don’t,” he hissed, taking a moment to analyze my new makeup and hair. My eyes immediately darted to the floor. I didn’t know what to say. Of all the reactions he could have had, I was the least prepared for this one. I stood there, silent.

  “Actually, I hate it,” he continued, the words shooting like knives off his tongue. “I hate the whole look. I hate the makeup and I hate the red lipstick.”

  I couldn’t help the tears that began streaming down my face, ruining the makeup I had been so excited about. I sank back onto the tufted stool. Was this really happening? He had never yelled at me like this before.

  “Don’t ever wear red lipstick again,” he warned me in a low voice and turned towards the door. I was utterly dumbfounded; it was such an irrational reaction to something so small. Even once he saw me crying, there wasn’t an ounce of sympathy in his voice; he only saw red (pun intended).

  He paused and turned back around to survey my reaction. Deciding he hadn’t done enough damage, he served me one final blow before storming out of the room: “You look old, hard, and cheap.”

  That was it; end of conversation. But that’s how disagreements always ended with Hef; he would just stomp off and you were left to pick the pieces of your self-worth up off the floor. I’d invested every part of myself in Hef and the mansion and had nothing waiting for me outside those gates. I felt so trapped and so vulnerable to his criticisms.
This old man had just humiliated me—and I sat there taking his ridicule like a child. I curled up on the vanity stool and sobbed for what felt like forever, in the one little corner of this whole giant mansion that was supposed to be my own. But even that wasn’t real. It was his world—all of it.

  He made no mention of the conversation again. When you’re the king of all you survey, you don’t really need to say much more. His point was clearly made. For many years his words rang in my ears: “old, hard, and cheap.”

  Who says that to a person they supposedly love?

  The whole episode made me feel beyond ugly, as if all the beauty products and cosmetic surgery in the world couldn’t make me look good. I felt like an idiot for even trying to be beautiful. Maybe I was just the homely girl who was “lucky” enough for Hef to allow into the mansion. That’s certainly how his actions made me feel. Needless to say, from then on, I stuck religiously to corals, pinks, and nudes, never daring to try red lipstick in front of him again.

  Just when I was starting to give up hope that I could ever find any real positivity in Hef’s twisted world, someone new caught my eye. I looked up from my book and adjusted the messy bun on top of my head that was disguising my poorly received new haircut.

  I wonder who that is, I thought. A bubbly Carmen Miranda–costumed blonde sauntered across the pool area handing out shiny beaded necklaces with tiny bottles of Jack Daniel’s attached to all of the partygoers.

  “Happy Cinco de Mayo!” The girl beamed, a huge, gleaming smile on her face as she handed me a necklace. She had a large, red headdress balanced on top of her head and seemed unusually perky.

  “Thanks!” I said, accepting the beads and watching her walk over to Hef’s backgammon table. How fun, I thought. Lately, I had become used to putting on a cheerful facade, since on the inside I was essentially Eeyore with a rain cloud following my every step. This girl was like a ray of sunshine so unlike the other Fun in the Sun party guests, all of whom spent the days self-consciously preening themselves while wearing boring basic bikinis. She seemed to glide right out of an old Hollywood musical!