Down the Rabbit Hole (5 page)

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.

C
HAPTER
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.

In those early days, Vicky and Lisa (two of Hef's live-in girlfriends) were incredibly welcoming—the other girlfriends weren't particularly mean, but they didn't exactly roll out the red carpet, either. I knew that the role of girlfriend was coveted by many and fleeting for some, so I expected the women to be defensive, protective, and, quite frankly, bitchy—especially this crop of girls who looked more like garden variety strippers than dazzling
Playboy
bunnies. I was surprised with how wrong I
thought
I was. They were accepting and encouraging—some more than others—and Vicky, one of the more seasoned girlfriends, even offered to take me under her wing as I navigated this new, foreign world. It really didn't occur to me that they had their own agenda, which I would soon learn.

The girls would rattle on about how glamorous it was being a “girlfriend” and how every girl that moved into the mansion would eventually become a Playmate; they all had a weekly allowance to buy club clothes and get their hair and nails done; and the afternoons free to spend however they like. As a girlfriend, you just needed to be available on the nights when Hef hosted events at the mansion, went clubbing in Hollywood, attended red carpet parties, etc.

This may sound naïve, but I didn't immediately realize that they were actually
required
to sleep with Hef. Back then, none of the girlfriends talked about it. When I inquired about the more intimate duties, Vicky fiercely denied that anything sexual went on with Hef.

“It's all for show,” Vicky said, explaining that the whole thing was basically a Hef-orchestrated publicity stunt.

The girlfriends were simply dazzling arm candy to help keep up his
Playboy
image. It sounded more like a job than an actual relationship—and they sold it to me so matter-of-factly I was able to overlook what this “job” really sounded like. Hef's former girlfriend Katie Lohmann had recently left, and Vicky told me that when she went on Howard Stern after scoring her centerfold and cheerfully denied that any of the girls slept with Hef with a dismissive laugh, she was promptly kicked out of the mansion. (Years later I found a taped copy of the interview in Hef's press collection with a skull drawn on the label. He must have really hated that one!)

I would be lying if I said I still didn't have dreams of one day scoring a pictorial in
Playboy
's iconic pages, and mansion parties were a fun way to spend the weekend, but my main focus was either pursuing an acting career or going back to school. I didn't have time to be Hugh Hefner's on-call trophy girlfriend seven days a week, nor did I really think I had what it took. When I first started coming around, Hef was dating the Bentley twins—those two sophisticated glamazons that seemed to pay homage to the glory days of
Playboy
. With the right hair and makeup, I considered myself a pretty girl, but Mandy and Sandy looked like movie stars. After they departed the mansion, the “Sloppy Seven” invaded and lowered the bar.

It's almost unsettling how quickly your priorities can shift.

Over the past year, I had been working long hours to afford my rent and I'd been auditioning like crazy. Luckily, I had no trouble getting an agent—and even managed to land a few bit parts here and there. They didn't pay much, but it was enough to encourage me to continue pursuing my dream. My two closest friends hadn't been as fortunate. Heather had given up and decided she was moving back to Pittsburgh. My roommate Nora hadn't landed a single thing, either. The lease on our apartment was ending and she told me that her parents had agreed to pay her rent on a new lease—but only if she had her brother (an alcoholic who needed constant babysitting) move in. Just like that, I had to go.

It was like that scene in
Bridesmaids
where Kristen Wiig gets booted from her apartment by Rebel Wilson and her on-screen brother—only not funny. Nora knew I had no credit and was broke as a joke; I couldn't believe she was doing this to me. But as hopeless as the situation seemed, I refused to go back to Oregon. Not only did I not want to burden my parents, I also knew that leaving now would set back any progress I had made in becoming an actress. The desire to perform is what drove me to Los Angeles, and the thought of returning home miserable and still dreaming of Hollywood killed me.

I started to wonder,
Couldn't Playboy help me reach that goal?
I'd seen it before:
Baywatch Hawaii
executive producer Michael Berk was a mansion regular and Hef's former girlfriend Brande Roderick landed a leading role on the show shortly after appearing as a centerfold. The more time I spent at that enchanting Holmby Hills compound, the more I started seeing opportunities like these. It's very easy to get transfixed by the magic of this curious world where even the impossible seemed possible—where a small-town girl could rub elbows with movie stars and be made to feel like a fantasy. I had spent so much of my youth searching for that kind of opportunity and it seemed
Playboy
could hand it to me on a silver bunny emblazoned platter. One weekend while waiting outside of the mansion's front door for the valet to pull up my beat-up old car at the end of a “Sunday Funday,” I looked up at the glowing second-story windows and wondered what it would feel like to call that place home. It looked so cozy and safe.