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

by Holly Madison

  After a few days of recovery where I felt like an elephant was sitting on my chest, I finally made it to the mall to buy my first post-surgery bra. As I tried on a handful, I finally found a perfect fit. I looked at the tag on the lacey white Victoria’s Secret Dream Angels bra: a 34D! The surgeon had told me he couldn’t guarantee what size my breasts would end up being—I had asked for a C cup using a topless photo of a Playmate as inspiration. I couldn’t believe I was a D cup—I was huge!

  While I don’t regret the surgery (I couldn’t have been happier with my body), the credit card debt would end up becoming too much for me to pay off in a timely manner—contributing to money troubles that would end up haunting me in the years to come.

  Shortly after the surgery, with roughly $100 in my bank account, I packed up my battered red Toyota Celica and made my way, like countless girls before me, down the Pacific Coast for a chance at “making it.” After two years at Portland State University, I transferred my credits to Loyola Marymount, a private university about five miles south of Santa Monica. I was earning a double major in psychology and theater arts and figured there was no better place to study acting than in L.A.

  Student housing was already at capacity when I arrived, so transfer students were put up at a hotel across from campus (two students to a room) until we could make other arrangements. I thought it was so cool getting to live in a hotel and I didn’t want to have to move out after my first semester. Not to mention, apartments in Los Angeles were really pricey and I was anxious about having to eventually factor that into my already tight budget.

  I hadn’t been in Southern California more than 24 hours before I realized I needed a relatively well paying job—and quickly!

  At a friend’s suggestion, I headed to the Hooters in Santa Monica to apply for a waitressing gig. Much to my surprise, I was hired on the spot.

  Thank God for my new boobs, I thought.

  My first day on the job, the manager handed me the signature “Hooters Girl” outfit and motioned for me to go change. When I emerged from the stall in the women’s restroom, I paused to take a long look at myself in the mirror.

  How can I go out on the floor in this outfit? I thought. I had never felt so naked in an outfit before. The breeze of the air-conditioning went right through the thin tank top and tiny spandex shorts as if I wore nothing at all. And the shorts were so tiny, the girls’ butt cheeks always hung out of the bottoms. I often thought the restaurant should have been called Cheekers. The only blessing was the nylons. Hooters Girls were required to wear tan pantyhose to make their legs look flawless, but to me they also added a measure of decency.

  Suck it up, Holly, I thought. My dream was always to make something of myself, and by allowing me to afford to stay in L.A., this job was a means to that end. I had read an article about Hooters Girls in Jane magazine that highlighted how much cash they earned in tips. There was no way I was giving up this opportunity.

  I fixed my hair, put a smile on my face, and walked out the door. And you know what? It really wasn’t that bad. I soon learned to love my job.

  After a short time in the city, I settled into a tiny Westwood apartment with my friend Nora. Besides a mattress, a lamp, and a pile of schoolbooks, my room was all but empty. My Hooters salary was barely covering my daily expenses, so I relied heavily on scholarships in order to pay for a portion of the hefty tuition at the private university. What was left over for me to pay? . . . Well, let’s just say it went unpaid for quite some time.

  I was 20 years old and almost delusionally confident and optimistic. I was convinced I could do anything I could put my mind to . . . even become a famous actress and get my college degree within a few years. I knew I wasn’t always the hottest girl in the room, but I also knew I wanted success so badly that I would work harder than anyone else for it. For a while, I did manage to juggle it all: the school, the job, and the auditions. There was only so much longer I could keep up it up, though. I was burning the candle at both ends and something was bound to give.

  As it happens with transfers, many of my credits from Portland State didn’t apply towards my program at Loyola Marymount. In order to graduate on time, I’d have to load up on credits, which included long theater hours that would require working backstage on different productions during the evenings when I typically waitressed. I knew that with a packed school schedule and a full-time job, I wouldn’t have any time to study. And if I couldn’t study, I wouldn’t be able to meet the minimum grade requirements of my scholarships. So after a year at LMU, I decided to take a break from school to focus on pursuing my career. I would never be as young or as eager as I was in that moment, and I figured that I might as well take the plunge. School would always be there, so if it didn’t work out for me, I could easily go back and finish my degree. It’s not unusual to graduate from college at 30; but it’s a lot less likely to break into acting at that age. In my heart, I thought it was the best decision for me at the time.

  With school on hold, I picked up more shifts at Hooters and eventually started working part time as a Hawaiian Tropic model. The gig basically required me to show up at events in company apparel or appear in movie bit roles in swimwear and a “Miss Hawaiian Tropic” pageant sash. I thought it would be a great way to make extra money and also to meet people. In Hollywood, you never knew where opportunities would arise. I would end up being right, of course. The gig would lead to something, though maybe not what I had expected.

  Not long after, at a Hawaiian Tropic Bikini Contest in Beverly Hills, one of the event organizers pointed out an older man.

  “You see that guy over there?” he asked. “That’s Hugh Hefner’s personal physician.” Naturally, it was exciting that someone associated was Playboy was at the event, but I didn’t give it too much consideration until an hour later when the man approached me.

  “Would you be interested in attending a party at the Playboy Mansion?” he said, barely taking the time to meet my eyes. My mouth fell to the floor. He posed the remark as a question, but it was clear he already knew there was only one answer.

  He’d apparently been at the party offering invitations to the girls he deemed Playboy-party worthy. It wasn’t abnormal for a representative from the magazine or one of Hef’s friends to invite attractive women to the parties. Many of my coworkers had become regulars at the mansion. I guess I just wasn’t expecting an invitation of my own, and especially not from his doctor of all people.

  Was he really asking me if I want to go to the Playboy Mansion? I thought. For a starstruck girl from Oregon, this felt like the chance of a lifetime.

  “Are you kidding?” I squealed. “Of course!”

  In Los Angeles in 2000, there was only one invitation that mattered: a Playboy party. Nowadays, invitations to the Playboy Mansion are sold to the highest bidders and to any media outlet offering any morsel of publicity. It’s no longer considered exclusive or coveted. But back then? It was the place to be. Hef threw only a handful of parties each year with a maximum capacity of about 800—and the guest list was strictly invitation only.

  When I received my glossy black invitation in the mail a few days later, I could feel my heart swell with excitement. “Hef’s Midsummer Night’s Dream Party,” it read. On the front was a beautiful pinup illustration by famed artist Olivia De Berardinis and inside was a small piece of paper with directions. It was like Cinderella finally scoring an invitation to the ball—except instead of arriving by horse-drawn carriage, we would board a shuttle at a UCLA parking garage.

  The dress code was strict: “Sleepwear Required.” My coworker Heather had also landed an invitation—a huge coup for me considering invitees weren’t allowed a “plus one”—so we immediately starting obsessing over what we would wear.

  Despite having very little flexible income, I decided I needed a new lingerie set from Frederick’s of Hollywood: a black satin corset with matching garter belts, thigh-high stockings, and a short yet conservative silk robe to wear on top of the ensemble. Bi
kinis and Hooters shorts aside, it would be a little while before I would be comfortable parading around in “lingerie or less,” the staple look at a Playboy party.

  ONE BY ONE, GUESTS stepped off the shuttle. Every inch of the estate seemed to sparkle. Bright white twinkle lights lit the walkway towards the decadent soiree; gorgeous colored spotlights draped the cascading waterfalls framing the pool. Both Heather and I were so overwhelmed we barely spoke a word to each other as we took in the magnificent grounds. Before we entered the party, a staffer asked to take our photograph. We didn’t even question why as one by one each woman stood for a Polaroid. When we finally made our way around to the backyard, we spotted the most lavish buffet of food I had ever seen.

  For two broke waitresses who existed mainly on Top Ramen and chicken wings, it was a feast fit for royalty: seafood bars, carving stations, sushi buffets, dessert carts, and gorgeous-looking drinks flowing from the flagstone bar next to the pool.

  Suddenly Heather jerked my arm and pointed across the lawn.

  “Oh my god, there’s Cameron Diaz,” she said, pointing to the tall beautiful blonde sitting at a table nearby. And next to her was Jim Carrey. Across the pool, Heather spotted Leonardo DiCaprio! It was a virtual who’s who of Hollywood!

  “Holly! Heather!” We heard our names through the crowd. Who could we possibly know here?

  It was a welcome relief to see our friend Kira, another Hooters server, waving to us from across the party. She navigated her way through the sea of people with the expertise of someone accustomed to these types of events. Working together, I knew that Kira had seen her fair share of Playboy parties.

  “You guys want a tour?” She posed the question as if we had just happened into her very own living room, and we immediately took her up on the offer. She walked us through the infamous candlelit grotto (which was still empty at this early hour), through the zoo where we fed grapes to the tiny monkeys, and inside the ’70s-themed game house before making our way into the main event. Gorgeous colorful fabrics clung to every corner of the grand tent rooftop, while faux grass lined the bottom, creating the illusion of some fantastical forest (although I’m quite certain that many of the people in attendance didn’t make a habit of reading Shakespeare, and, in some cases, quite possibly had never even heard of the play the party was named for). Everything looked so sensuous and inviting.

  It wasn’t until we were tucked away in a corner of the tent that I finally spotted our infamous host looking quite gloomy—especially for a man flanked by two of the most breathtaking beauties I had ever seen. The Bentley twins were tall, tan, and reed thin with slow, languorous walks. They conducted themselves like royalty—as if they were on the arm of a king or a president—but were dressed like sex kittens in custom-tailored Baracci costumes. Shimmering with beads, sequins, and Swarovski crystals on French lace skirts and tops, their outfits were unlike anything any other partygoer was wearing. They were sexy but oh so elegant, with perfectly painted faces and blond cascading curls decorated with glittery butterflies. They were picture perfect and, needless to say, made a lasting impression.

  “He never stays for that long,” Kira said, when she saw me looking over at Hef and his fabulous girlfriends. I watched as Hef sat in a crowded corner of the tent, shaking hands with one partygoer after another. My first thought was that he appeared really out of it. Was he senile? I thought. More likely, he was just bored. After 50 years of glad-handing, I’d imagine you’d get sick of it, too.

  I knew I didn’t have long before he made his escape, so Heather and I headed towards his table to introduce ourselves. Maybe Mr. Playboy would see me, think I was pretty, and suggest I audition for a pictorial. It was a long shot, but I figured it couldn’t hurt. Stranger things could happen.

  “Hi, I’m Holly,” I said, sticking out my hands to meet his.

  “What’s that?” he asked, clearly having trouble hearing over the crowd.

  “I’m Holly,” I repeated, a little louder.

  “Oh, hi. Nice to meet you, darling,” Hef said before turning his attention to the next person. There were no fireworks, no “Rhapsody in Blue,” and there certainly wasn’t any audition.

  Oh well, I thought, I gave it a shot.

  CHAPTER 2

  In another moment down went Alice after it, never once considering how in the world she was to get out again.

  —Lewis Carroll, Alice’s Adventures in Wonderland

  A year after my first Playboy Mansion invite, I had become something of a fixture at the infamous Sunday “Fun in the Sun” pool parties. After that fateful Midsummer Night’s Dream party, Heather and I started getting invited back to the mansion regularly. What wasn’t to love? Bikinis, drinks, food, music, and friends. And without fail, the sun was always shining on Hef’s little corner of heaven. He wouldn’t have had it any other way.

  Without the massive tents and fake grass that the staff sprawled out for the Midsummer Night’s Dream soirees, you could really appreciate the true beauty of the property: lush landscaping, rolling green hills, and exotic birds that roamed freely throughout the grounds. It was unlike anything I had ever seen before—it was truly an oasis in the middle of Los Angeles and a life so unlike my own that I almost envied the women that were able to call this magical place home.

  Of those women, the glamorous Bentley twins had already exited the mansion by this time, leaving an opening for a new crop of blondes to emerge—most of whom also wound up being published in the magazine as Playmates in rapid succession. In the Playboy culture, it’s considered an honor to be chosen as the magazine’s Playmate of the Month (the large pictorial includes a poster folded in the center of the issue, hence the name “centerfold”). An even bigger honor was to be chosen as the magazine’s Playmate of the Year. Every June, a winning Playmate is selected from the previous year’s 12 candidates and is awarded $100,000, a new car, a new pictorial, and a cover. Most girls who rotated through the Playboy revolving door prayed that they might eventually be chosen as a Playmate so that their names would be in contention when it came time to choose the Playmate of the Year.

  Hef’s new girlfriends weren’t all necessarily Playmates, but they definitely all aspired to be. In fact, to an outsider, it could easily be misconstrued that the only way a blonde was eligible to be featured in the magazine was to date its editor-in-chief. Month after month, they appeared: Brande Roderick, Buffy Tyler, Katie Lohmann, Kimberly Stanfield . . . Tina Jordan and three of Hef’s other girlfriends were in the process of shooting soon-to-be-published Playmate pictorials as well.

  Hundreds of women were invited to each mansion party, so of course not all of them could be Playmates. Some of the Playmate hopefuls unable to land one of those 12 coveted spots modeled for less prestigious “minor pictorials” in Playboy or for pictorials on Playboy.com.

  The guest list for the Sunday pool parties was much more selective, so I have to admit, I was flattered to have been included. Only 20 or so girls were invited to these more intimate events splashing the day away. Yet it was rare to see any of Hef’s then seven girlfriends at the pool party for any length of time. I remember it striking me as odd that they chose to hole away in their mansion bedrooms, but I didn’t give it much thought beyond that. (I would later realize that they considered it dues they no longer needed to pay.) As for Hef, he would tuck away in a corner of the pool and play backgammon with two friends—usually the only other males allowed to be in attendance. Occasionally they would stride over and join the girls in a drink or a game, but they mostly kept to themselves and always focused their attention on Hef. After all, they wanted a repeat invite and Hef, without actually saying a word, made it clear that the girls were solely for his amusement. The staffers—who strictly refused all tips—were readily available to wait on us hand and foot, the mansion gym was available to any of the girls who wanted to work out during the party (perhaps a red flag to the expectations placed on the women of Playboy), and a masseuse was on call in the bathhouse for guests looking to
further unwind.

  One afternoon I was freshening up in the bathhouse and talking with a girlfriend when a buxom woman named Nicole bounded in and introduced herself. She was very sweet, but I could barely stop gaping long enough to get a word out. This woman had the largest breasts I’d ever seen, so large that it looked like the implants were struggling to escape from under her skin. The masseuse had to go rustle up an extra stack of towels just so Nicole could lie on her stomach for the treatment. (Years later, I was flipping through an issue of Playboy and recognized the busty blonde from the bathhouse—only this time her name was Coco and she was married to the rapper Ice-T. It’s been her booty that has earned her the most attention, but strangely enough I didn’t notice her butt as unusually large back then. Probably because I couldn’t take my eyes off of those boobs!)

  When the light would eventually dip below the hills in yet another picture perfect sunset, the service staff would busy themselves with preparations for the evening’s dinner and movie screening. The pool party guests would excuse themselves to freshen up as the festivities moved inside. Eventually, some of the girlfriends would trickle down from upstairs and idly take their obligatory seat next to Hef at the dining table for the pre-movie buffet. I could never understand their lack of enthusiasm; they seemed to have it all. Initially, I assumed they were spoiled, jaded, or just not a good fit in Hef’s world—maybe they hated the social scene or hated watching old movies every week. Since those were things I happened to love, I couldn’t understand it.

  Because I was an L.A. transplant, the concept of “being fake” was still a bit lost on me. Don’t get me wrong; I was familiar with fake tans, fake nails, and of course fake boobs, having already undergone my breast enhancement surgery. But I didn’t have any idea how insincere and calculated people could be. It never dawned on me that the girls I was about to be spending a lot of time with had ulterior motives beyond simply being friendly, and that all of their encouragement was just for show. As I’d come to learn, they saw me as a useful pawn in their twisted game of Playboy chess.