Down the Rabbit Hole (4 page)

Thank God I said something. Although after signing the paperwork, I'm pretty sure the editors could have done whatever they wanted with my photo. Yet, while I didn't want to end up in some throwaway section of the magazine, I had to admit I felt a bit defeated. I thought I'd blown my opportunity to appear in
Playboy
.

It wound up being six years—and a very strange twist of fate—before my next chance at a pictorial.

In the meantime, I'd decided to transfer schools so I could make my way to Los Angeles.

Before I left, however, there was one thing I needed to do.

I
TOOK A DEEP
breath as I plunked three brand-new credit cards down on the receptionist's desk. Like every college student, I had received a slew of credit card offers in the mail and applied for as many as I could get. Since the limits were so low, it took three cards to cover the $7,000-plus my new set of breast implants would cost me.

As each card swiped through the machine—maxing out one after the other—I carefully filled out the paperwork with nervous excitement. You might think my failed
Playboy
casting was the reason I was now sitting in the doctor's office preparing for an expensive cosmetic procedure, but that was really just the straw that broke the camel's back. For the past several years I had struggled with insecurities about my chest—or lack thereof. I'd always been naturally curvy from the waist down, but from the waist up, I was as skinny as a stick figure.

This had plagued me through high school and I spent those years perpetually armed with a heavily stuffed Wonderbra. I wasn't trying to appear stacked per se—I was just trying to balance the proportions of my body while I waited for the bombshell chest I was certain I would one day develop. I remember gaping at Anna Nicole Smith's
GUESS
ads when I was in junior high, hopeful that I would be just as voluptuous one day, but it never happened. (I even sent away for herbal supplements “guaranteed” to increase your chest by two cup sizes! Surprise! They didn't work. I actually called and got my money back.)

The nurse led me into the preop room and instructed me to change into the scratchy hospital gown. I had never had even the most minor surgery before, but I was young, fearless, and determined to look my best. After all, you only live once, right? I was sure I would pay the credit cards off in a timely manner. It was no big deal.

After the procedure, I woke up feeling like I had been run over by a garbage truck. The doctor had made the surgery sound so simple during my consultation that I actually thought I would be up on my feet that same day. Foolishly, I planned on keeping the entire ordeal a secret from my parents. I wasn't in the habit of discussing my private anatomy with my mom and dad, and since I'd been stuffing my bras religiously for years, I figured they wouldn't even notice. There was
no way
they would have allowed me to pile on all this massive credit card debt in one swoop, but I didn't want to hear anyone's advice (I was always one of those stubborn kids who insisted on learning things the hard way).

The nurse rolled me out of the facility in a wheelchair to meet my friend who was scheduled to pick me up. Slumped over in the passenger seat, I realized there was no way I could keep this from my parents. After she pulled into the driveway and walked me to the front door, I not so gracefully stumbled through the entryway and flopped on my parents couch, clutching a barf bag full of bile to my chest. In this state, I had to explain the whole ordeal to them as they shook their heads with a mixture of amusement and amazement. Luckily for me, I had long been rebellious and they were used to my crazy antics.

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. Bikinis 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.

O
NE 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.