Down the Rabbit Hole - Holly Madison

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.
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