Down the Rabbit Hole - Holly Madison

prop pipe (say that three times fast!) to pay homage to my boyfriend (the Hef tribute had been done
once before by his second wife, Kimberley, and would be done again by his third wife, Crystal). The
remaining selections felt more downscale stripper than the old Hollywood glamour style that I would
have preferred.
“Can’t you see too much?” I asked timidly. This was Playboy, I thought. Not Hustler.
“No, you can’t see anything from this angle if you lean forward,” the photographer reassured. “I
swear.”
The photographer assigned wasn’t one of the two used to shoot the Playmate pictorials, and I
was worried that I was wasting my time. Since I wasn’t getting the opportunity to shoot with the best
of the best, I was terrified that my photos weren’t going to be the home run I had hoped they would be.
Despite what my gut was telling me, I continued with the shoot. I didn’t want to seem ungrateful or
bratty.
“How did the shoot go?” Hef asked when I appeared in the master bedroom. After a long day
(which included a car wash scene, in February) I was cold and exhausted and wanted nothing more
than to shower and crawl into my pajamas.
“I’m not sure,” I answered honestly. “I don’t know if I’ll like the photos.”
When the slides came back (Playboy was still shooting on film in 2003), I hated them. As I
predicted, they were far more explicit than I wanted them to be. I felt like a fool for listening to that
photographer.
Adding insult to injury, the slides were accompanied by a memo from Playboy’s Chicago photo
editor, saying something to the effect of: “Hef, do you want us to use these? They look like they were
shot in your room with her wearing your robe and smoking your pipe.”
The comment made it sound like I was some interloper sneaking around the Playboy Mansion
taking photos without permission. Was the editor not aware that I was Hef’s girlfriend? I felt so
embarrassed. Usually, Hef made such a public fuss over whoever his main girlfriend was—I felt like
I was the first one he neglected to do that with. It made me feel like I was not beautiful or glamorous
enough to merit such praise. In hindsight, I know he was just sick of the high turnover with his past
girlfriends. They were lasting, on average, about six months, and he was done floating any girl’s ego.
He had come to the conclusion that if he kept us broken and needy, we would stay.
Broken and needy were definitely two adjectives that perfectly described me during that time.
After about a year of stubbornly trying to maintain some semblance of individuality, I finally gave up
on my short hair and started wearing clip-in extensions to give me the long hair Hef preferred. I was
feeling more disconnected than ever from the goals I once had; mansion life had eaten away at my
self-esteem. I found myself constantly trying to compete with the other girlfriends who were all caught
up in who was prettiest. It was a perpetual contest to see who could be the skinniest, tannest, bustiest,
most baby-faced with the longest, whitest hair.
We were all striving to win. We were trying so hard to stand out and be coined the “hottest” of
Hef’s harem that we completely missed the fact that we were making ourselves indistinguishable from
one another.
After thinking about it for a few days, I finally worked up the courage to ask Hef to scrap my