Down the Rabbit Hole - Holly Madison

Playboy’s “Millennium Playmate” search was coming to Portland. Immediately, my mind started to
wander. I found Oregon’s weather depressing and didn’t feel like opportunity exactly lurked around
every corner there. I had been thinking a lot about moving to Los Angeles to try my luck, but I didn’t
know anyone in L.A. or have the financial means to make such a big move.
Apparently, according to the report, the magazine had been conducting a nationwide “on the
road” search for the “Millennium Playmate.” A gigantic tour bus traveled the United States (and
Canada), stopping in 45 cities testing candidates. The girl chosen would receive $200,000, would
appear inside the January 2000 issue of Playboy, and would be flown around the world to represent
the men’s magazine for the entire year. It sounded like just the opportunity I was looking for!
This wasn’t the first time Playboy popped up on my radar. As was true with many children of
the ’80s, it wasn’t abnormal for us to have a Playboy magazine arrive at the house. I even remember
my mom and dad studying the front cover of a Playboy once to find the hidden rabbit head. As a kid,
you think that sounds like a pretty fun game, but we were quickly told that it was “for adults only.”
One day my sister and I were scouring the house for any Christmas presents my mom may have hidden
when we came across a few Playboys that had been hidden away. We flipped through in absolute
hysterics, pointing out all the bare butts. I was a kid, so I thought it was hilarious!
While Playboy wasn’t completely foreign to my home, it still felt rebellious. I knew that if I
auditioned for the “Millennium Playmate” and happened to be chosen, my parents wouldn’t be
thrilled at the prospect of me posing naked, but possibly would have respected my decision. It was a
reputable magazine with a storied history, so it felt edgy but also somehow safe.
Plus, at the time many of Hollywood’s biggest stars were appearing in the magazine: Cindy
Crawford, Jenny McCarthy, Drew Barrymore, etc. Not to mention, my icon Marilyn Monroe was
Playboy’s first ever cover girl. Naturally, I too had pipe dreams about one day being in the magazine.
This is perfect, I thought. I’m going to audition!
According to the news report, the process was quite simple: call the provided number, make an
appointment, and show up with your favorite bikini.
That’s when my genius idea to fast-track my stardom hit its first speed bump: I didn’t actually
own a bikini. In my defense, I lived in Oregon. Why would I need a bikini? And when I say things
were tight financially, I mean they were tight. But I decided it was about time to make an investment
in my future. After calling the number, getting the address where the bus would be stationed, and
securing an audition time the following week, I went shopping.
Needless to say, Portland wasn’t brimming with retail shops specializing in swimwear, but I
remembered seeing one downtown near my college campus, so I popped in to see what I could find. I
didn’t really know where to begin. Obviously, I had never taken photos in a bikini before (this was
about 15 years before “selfies” became popular), so I didn’t know what I should be looking for. After
scouring the racks for the best deal, I decided on a silver metallic bikini that was both sexy but also
one that I felt reasonably comfortable in.
Before the audition, I figured I should probably get some kind of tan. There weren’t too many
sunny days in the Pacific Northwest, so my complexion was incredibly light (particularly when
coupled with blond hair and a silver swimsuit). I went to the nearby tanning salon and had my first