Down the Rabbit Hole - Holly Madison

“People assume that I came here wanting to be a Playmate and that that’s my goal,” I said. “The
choice is extremely clear to me. I would much rather be Hef’s girlfriend. Hef and I are so much in
love. That’s not even a comparison to me.”
But just because I valued being Hef’s girlfriend didn’t mean I still wasn’t dying for a pictorial!
In fact, the two things had become intertwined in my mind. Since the ’50s, all of Hef’s main
girlfriends had appeared inside or on the cover of Playboy—except for me. And by this point, it was
humiliating. People would always ask me why I wasn’t featured in the magazine and I felt the need to
make excuses for it by convincing people that somehow I was special because I wasn’t. Hef was
keeping me for himself, I would explain. What else was I supposed to say? My boyfriend thinks I’m
ugly?
My shock and joy was genuine when Hef revealed that we would be shooting for the magazine.
None of us expected it, so the reactions the cameras caught were absolutely sincere.
I’ll give the man this: he knew what made for good TV.
He also knew the importance of good timing. By allowing us to appear in the magazine, Hef
would be cashing in the biggest insurance policy he had to keep us safely behind the mansion bars.
But Hef knew something we hadn’t yet figured out: the show was positioned to be a runaway hit for
the network, so he no longer needed the magazine as a guarantee. He had better bait: fame.
The debut season’s arc revolved around our feature and possible cover. It wasn’t until about
halfway through season one that shooting began for the pictorial.
Hef allowed us to choose between the two staff photographers for our pictorial: Arny Freytag
and Stephen Wayda. For years, I had seen countless Playboy photo shoots come through Mary’s
office and I had absorbed every detail from conception to execution, from the first click of the camera
to the ink on paper. I was so excited to finally be a part of that process myself. You would think that
dating the magazine’s editor in chief would have afforded me a sort of security and confidence before
shooting the pictorial, but it was the total opposite. We couldn’t have been any more anxious about
the ordeal. We were way more nervous than just some random girl plucked from obscurity and thrown
into a shoot. We had firsthand knowledge of just how fickle and critical Hef could be and we were
petrified that we would somehow screw it up and he would just scrap the entire pictorial. After
talking to a handful of Playmates, I decided we should go with Arny. While Stephen is an extremely
talented photographer, he worked best with more experienced models who knew how to move in
front of the camera. Arny worked best with rookie models; those straight-off-the-farm girls who
needed help posing every inch of their body. When you haven’t done much of it, modeling can be
quite a clumsy sport. Kendra, Bridget, and I needed help squeezing our three bodies into an 8.5" ×
11" frame—while looking as amazing as possible.
The day of our first shoot I was absolutely ecstatic. We were told to arrive to the mansion’s
bathhouse in the morning for hair and makeup wearing nothing but a robe and slippers (tight clothes
and shoes would leave lines on the body—and we couldn’t have that!). I couldn’t believe I was
finally getting the full Playboy beauty treatment. For years I had watched girls transform into these
glamorous creatures with the help of the expert editorial beauty team. Even with my weekly
allowance, I would have never been able to afford the beauty team Playboy magazine used. In the