The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention (7 page)

With all that bluster, it seemed only natural, somehow, that Donald Trump was the person that brought us together again.

Trump’s Miss USA Pageant was being televised from Planet Hollywood and I was asked to be a judge at the last minute. It made sense for the casino to include me, since the pageant would be a network television event, and I was set to be the casino’s new headliner. I chose a long leopard-print Roberto Cavalli gown and sparkling chandelier earrings to wear. When I saw the program that included the names of the other judges, I noticed that Cyndi’s name was also on the list. She had been a pageant queen at one point herself, so she was a natural choice to judge.

Cyndi was playing double duty as a red carpet reporter for the event
as well, and when I saw her on the event’s “green carpet,” I fearlessly waltzed right up to meet her glare.

“Hi, Cyndi!” I exclaimed, as if I had nothing to fear from her. In reality, I shouldn’t have. I never meant to start anything with this woman, so there was no reason for anything but positivity, in my opinion. “I just wanted to clear up any confusion. I never meant to insult your outfit that day at the Palms. I meant what I said as a compliment.”

“Well, what do you think of what I’m wearing now?” she asked, gesturing down to her dress and brushing off my apology.

“It looks great!” I replied with a big smile, nervous as to what was coming from her next in front of everyone lining the carpet.

“Oh, good,” she purred facetiously, “because I would be soooo disappointed if you didn’t like it.” There was no mistaking her intentions. Her voice was dripping with undisguised sarcasm.

I smiled, ignoring her undertones, and waited politely for her to thank me for the “interview” and dismiss me. She launched into a few questions, very much along the lines of “What do you
know
about the history of the Miss USA pageant?” and “Have you ever had
any
affiliation with the pageant world yourself?” Her face was grim, as if she were asking me about important world events. Whether she intended it or not, I perceived a subtext: you’re not qualified to be a judge, so why are you even here? I saw Jim, the columnist, posted on the carpet nearby, wearing a huge grin on his face. Later that week his column recounted the interaction. Thankfully, he reported that we made peace. After that debacle, I learned to be a bit more prudent when it came to what I said and to whom.

I was diving headfirst into a crash course on how the media can easily spin anything into misconception. Press can work
for
you, but it can just as easily work
against
you. When I was invited for a complimentary manicure at the opening of a new salon in Town Square, I was aware that it was basically a staged photo op. I got a manicure, the photographers got a photo, and the salon got some press—everyone wins! The following
week the photo was printed in a weekly celebrity magazine. I was shown looking over my shoulder at the camera, a huge smile on my face while I was getting my nails done. The caption read: “This is what she was used to at the mansion!”

Benign as this may have seemed to whoever wrote it, I found the caption terribly irritating. It implied that I couldn’t afford to get my nails done anymore and that this was a rare treat, reminiscent of my days living in Playboy luxury. In reality, I was making more money than I ever had, all on my own. Not to mention, I was completely independent and could get my nails done whenever I liked, without having to worry about being back by curfew, thank you very much! I was proud of myself for landing on my feet even though the odds were against me and I could easily have ended up flat on my face after fleeing the mansion. Was it a bad thing that I wanted everyone to know how well I was doing? I didn’t think so. It’s a good message—to know that you can stand on your own two feet even if everyone is telling you that you won’t be able to.

“This is so frustrating!” I complained to Hannah, passing the magazine over to her as we ate lunch in my suite. “Everyone thinks I’m flat broke. I don’t care if they think I have money or not, but I do want everyone to know I’m working! Not to mention happier and better off than I was a year ago!”

“Well, that’s what you get.” She shrugged, plucking a single potato chip and placing it into her red-lipped mouth, flicking the crumbs off her glossy black nails.

It struck me as an odd thing for her to say.

“What do you mean?” I asked incredulously.

“When you put yourself in the public eye, you are inviting everyone,
including the haters
, to make assumptions about you,” she explained. “It’s your job to change the conversation if you don’t like what they are saying. You have to take control of your own narrative. My dad has to deal with this kind of shit with his business all the time, and it’s not always easy.” She paused, giving it a bit more thought. “Frankly, I think it’s going to be
an uphill battle for you because you’ve been so synonymous with Playboy all these years.”

Her phone buzzed, quickly diverting her attention, giving what she said to me a moment to sink in. I wasn’t expecting such an informed lecture from Hannah, but you know what? She was a hundred percent right. I was going to have to work my ass off in order to change anyone’s mind. My thoughts started to wander back to all the things I wanted to accomplish.

For the next three months, I would be starring in the hottest revue on the Vegas Strip. It was a job I landed on my own—without anyone’s help. That was a huge victory for me. It also meant a certain level of security, because for twelve weeks, I had a steady large salary. When I wasn’t busy trying to sell a TV show, I spent all my free time doing press and appearing at events. After my three months were up, I wanted
Peepshow
begging me to stay on.

My schedule was about to go from packed to absolutely insane. I knew I wouldn’t be able to keep up with it anymore, so I hired Angel as my assistant to help with the day-to-day things that could have easily fallen through the cracks. I became so busy that her help was well worth the money. The flexible schedule was perfect for her, since she had just given birth to her adorable son, Roman. Laura had arrived in town shortly before Roman was born and we had raced to the hospital with bags of Taco Bell (her favorite) in tow for the new mommy. The happiness I felt for Angel and the closeness of our little family of friends helped me feel less alone than I had in a long time.

With the top of my newly purchased convertible down, I cruised down Las Vegas Boulevard feeling the dry desert air on my skin. There would be bumps in the road, of course, but I was
on
the road to becoming the woman I always dreamed of being. At the end of the Strip next to the I-15, a glittering black-and-red billboard shimmered from above:
PEEPSHOW STARRING HOLLY MADISON!
And there I was, standing twenty feet tall.

Was this really my life?
I thought. I couldn’t believe how quickly the tide had turned for me and how fortunate I felt. Along with a new job and a new city, I felt like my personal makeover was nearly complete!

My life was finally beginning . . . and I was in for a wild ride.

W
ITH MY NEW FRIENDS
as my partners in crime, I made it a point to maximize my free time, going to as many shows, dinners, and events as we could squeeze in. If I was going to help make
Peepshow
one of the most popular shows on the Strip, I needed to know what we were up against. Nancy suggested we all check out a new nightclub featuring live dancers. She assured us that we wouldn’t want to miss her best friend Lindsay, who was performing there that night. I knew that my dancing skills had been sharpened thanks to my time on
DWTS
, but I didn’t have nearly the sort of professional training that many of these Vegas showgirls had. I felt intimidated that I’d be compared with them, but I was ready for the challenge and figured I needed to do my research. When I looked around this particular establishment, I saw a few dancers positioned on banquettes around the room. They were dressed in spangled bras and skimpy, cheap-looking boy shorts. One of them listlessly threw around a small, beat-up pair of feather fans. I knew there was better in the city that I had yet to see, but still hoped I could learn something from that night’s performances.

After we ordered a round of drinks, Nancy, Hannah, and I dove into a debate about who were the most eligible bachelors in Vegas. Right around the time that we were each taking a stance on whether we would ever date one of the more notorious (and handsome) nightclub promoters in town, Lindsay made her entrance. A hush fell over the restaurant as the longest pair of Wolford-covered legs I’d ever seen stepped one by one onto a platform in the center of the room. This bewitching woman was tall and ballerina thin, with a silky mane of dark blond hair tumbling down her back. Obviously a trained dancer, she performed a slow, sensu
ous number with the help of a well-tailored men’s white dress shirt. Her routine was elegant and clearly took skill—particularly because she performed it in the most towering pair of Brian Atwood platform stilettos I’d ever seen . . . without even so much as a single wobble.

“Now,
that’s
a dancer,” Hannah whispered to me, gesturing to the lanky beauty. She was right. This woman seemed so untouchable compared with the other performers who had populated the club earlier in the evening. What could she possibly be doing here? When her routine finally concluded, the room erupted into applause and the swan glided off her stage.

As she walked by, Nancy waved to her to come over.

“Your performance was amazing!” I said. “Come sit with us!” I continued, introducing myself to the glamorous creature.

“I’m Lindsay,” she said, a cheery smile on her face. “It’s so nice to meet you. I can’t wait to see your show! I’ve been seeing the ads for it all over town.” She took a seat next to us on the edge of the booth.

“I love your outfit,” I said. “Did you put it together yourself?”

“Yes,” she said modestly. “We provide our own wardrobe and routines.”

“You have such great taste,” I remarked, then decided to just be honest and blurted out: “Why are you working here?”

She must have been taken by surprise, as a ladylike laugh escaped her. She shared a brief version of her backstory with us: like me, she was a small-town girl from the Pacific Northwest. She had studied dance all her life, recently moving to Vegas to make a living doing what she loved. She proudly announced that she had just been hired full-time at one of the smaller topless shows in town. She seemed genuinely thrilled, so I tried to keep the surprise from showing on my face. What was this classy broad doing in that show? The one she mentioned was easily the sleaziest one I had seen so far.

I told her that I was starting rehearsals for
Peepshow
, and I was doing a tour around town and had yet to see such a skilled performance as the
one she just gave. Lindsay was new to town and clearly passionate about her dreams—something I could relate to. We exchanged numbers and vowed to get together soon.

When I wasn’t doing my own personal research for
Peepshow
, I was pounding the pavement to do everything I could to promote it. In order to make the biggest splash possible, I vowed to be seen anywhere and everywhere on behalf of my new project. One of the events I had been invited to was the Playmate of the Year celebration at the Palms. On one hand, attending seemed natural. I had directed Playmate of the Year Ida Ljungqvist’s first pictorial back when I worked at the magazine, and Angel and I were eager to go out that weekend. I loved the Palms, but . . . I was still trying so hard to get away from the Playboy brand that I wasn’t sure if being seen at this event was the best idea.

Prior to the party, I called Mary to get her advice. I didn’t know if Hef was even going and I wanted to find out. I didn’t want to go if things were going to be awkward. I knew she’d be honest with me.

“Of course you should come,” she said, before lowering her voice and briskly adding, “But Hef says you can’t bring your manager.”

“I was planning on bringing Angel anyway,” I said defensively. I was irritated, because I knew the stipulation meant that he assumed I was dating my manager. There was a strict “no boyfriends” policy for the women at Hef’s events, with very few exceptions (the girls needed to appear available, so unless they were dating a celebrity or an athlete who could add some cachet to the event, they were usually out of luck).

Hef wasn’t the only person to speculate that I was dating my manager or my publicist. A few other acquaintances had assumed that as well. Somehow a public perception of me had evolved wherein I was unable to carry on a professional working relationship with a person of the opposite sex without sleeping with him.
If I had never been involved with Hugh Hefner, would people still make those assumptions?
The misconception was annoying, to say the least. Mary reminding me of it only fanned the flames. I considered blowing off the event, but I felt challenged somehow,
like I needed to show up and let everyone see how great I was doing as a
single
woman.

The night of the event, I stepped onto the red carpet feeling confident. No longer was I dressing to placate someone else’s preferences; I looked like myself in an asymmetrical top, a feathered skirt, and tall leather boots. My hair was blown out silky and smooth, curling just past my shoulders, and my makeup was natural, save for a classic black cat-eyed liner.

We walked up to the check-in table, where Playmates were handed cheap adhesive name tags indicating her name and the month and year of her Playmate pictorial. For an event that aspired to be upscale, this touch was very high school reunion. Though I had appeared on four covers, I was never technically a Playmate, so there was no name tag waiting for me. But that’s okay. I didn’t feel like I needed the introduction.

Angel and I were directed to a table full of Playmates, most of them women I had worked with at the studio. It was nice to catch up. I may not have had the fondest memories of my personal time with
Playboy
, but I had enjoyed my professional time at the studio, or I would not have wanted to come to this event at all. After Ida’s presentation, I struck up a conversation with fashion designers David and Phillipe Blond, who graciously offered to dress me for a few upcoming events, which alone made attending the party worthwhile!