Down the Rabbit Hole - Holly Madison

messy room (which was tidied up substantially). My shoot was in Hef’s bedroom and was intended to
be reminiscent of old Hollywood. The beauty team styled me like a ’40s movie star (minus the red
lipstick) and the photographer draped me over an elegant wood staircase wearing nothing but a pair
of vintage peach marabou bedroom mules. It was the most beautiful I had ever felt. Like giddy
schoolgirls, we snuck into each other’s rooms to get a peek of one another’s shoot. Each setup was
unique and tailored to our personalities, so there was no competition and we were genuinely excited
for each other.
Stepping into the Playboy Studio in Santa Monica for our final shoot was surreal. It was the very
same studio I had nervously visited with my old friend Heather years earlier. We had decided to try a
Playboy Polaroid audition, praying that we would be selected. My life had come full circle, in a way.
While the journey wasn’t quite how I imagined it, I was arriving at the studio to shoot a cover for the
magazine.
Surveying the massive studio space, I immediately noticed that the crew had constructed an exact
replica of Hef’s bedroom for our set.
“Why didn’t we just shoot at the mansion?” I asked one of the crew members, totally
bewildered. He couldn’t produce an answer. No one could. I suppose Hef was more inclined to
waste thousands of magazine dollars rebuilding his bedroom rather than being inconvenienced for a
few hours.
Playboy photo editor Marilyn Grabowski used a page from a foreign issue of Playboy as
inspiration for our first setup: three identical brunettes piled on top of each other in bed. Throughout
the sequence, we couldn’t keep a straight face. Since none of us were ever remotely attracted to one
another, it never even crossed our minds to “act sexy.” Posing for such a risqué shot felt incredibly
awkward, but it turned out that the laughter worked in our favor because the photos ended up looking
quite erotic.
Finally it was time to shoot our cover. Marilyn positioned each of us on a slightly slanted bed
covered in silk sheets (that she constantly kept smoothing, draping, and switching), while Arny
positioned himself on scaffolding directly above us. Because we were nude and flat on our backs, our
breasts had to be taped up to produce the amount of cleavage needed for the cover. Contrary to the
quick sequence audiences saw, the cover shoot lasted several days. Our hyper-meticulous, Devil
Wears Prada–esque photo editor kept analyzing every excruciating detail down to the placement of a
single curl. She must have changed the silk sheets from black to white to black again a hundred times
—sending the photographer into a tailspin. Despite all of it, I was having the time of my life. The
white, skylight-lit studio pulsated with creativity energy and positivity. It was such a welcome change
from the musty atmosphere of the mansion.
“I wish I could come here every day,” I whispered to Bridget as we lay on the slanted bed.
“I know, me too,” she said.
During our lunch break, Stephanie Morris—a junior photo editor at that time—called us down to
her office to fill out “paperwork.”
Hef hadn’t spoken to us about how much we were to be paid for our pictorial, but we were
about to find out. Rates for amateur models start at about $25,000 per pictorial. In 2005, reality-star