Down the Rabbit Hole - Holly Madison

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.
Vicky had once given me a peek inside her room—and I was surprised at how much it looked
like the type of room I would have liked to have. The plush bed was covered in pink candy-striped
satin sheets and piled high with Playboy-branded clothing—free gifts for Hef’s girlfriends. Disney
paraphernalia was everywhere from a recent shopping spree at Disneyland—all on Hef’s tab, of
course. And a dreamy windowseat overlooked the backyard.
We even ordered cheeseburgers from the kitchen, which may not sound like much, but it was.
Once upon a time, Hef’s guests could order whatever they wanted from the kitchen, whenever they
wanted. It was even said that Jack Nicholson used to treat the mansion as a drive-thru back in the
’70s. He would call the butler’s pantry ahead of time, order a meal, and have it brought out to his car
as he drove up the driveway. After the food was delivered to him in a paper sack, he would
supposedly speed out the back gate without so much as a hello. Since then, guests’ access to the
kitchen became a little more limited, but Hef’s girlfriends could still order whatever they wanted, 24
hours a day. To me, someone used to scraping together pennies in order to eat at Burger King, this
was on another level!
I had to admit: the whole girlfriend thing was starting to look pretty appealing.
Around that time, a few of the girls had suggested that I come out with them for one of the
biweekly club nights. One of the girlfriends, Kimberly, had recently been kicked out, which meant
there was an open spot Hef was ready to fill. “Talk to Hef,” Vicky encouraged after I confided in her
about my housing problems. Never did it occur to me to simply approach him myself. It also never
occurred to me that the then-seven girlfriends wanted me around only because my “ordinary”
appearance was nonthreatening. They wanted to make sure whoever filled the empty space wasn’t
competition.
On Sunday, I worked up the nerve to mention the idea to Hef when he finally appeared poolside.