Down the Rabbit Hole - Holly Madison

out of a fairy tale. I didn’t know it then, but I would find myself returning to that neighborhood quite
regularly five years later.
The episode that marked the most immediate change for me, however, was definitely the one
called “My Bare Lady,” which focused on me interning under Marilyn Grabowski at Playboy Studio
West. Despite dating the boss, I didn’t find the internship that easy for me to secure.
Prior to the start of each new season, the three of us girls would meet with producers to discuss
the coming months and potential plotlines they could follow. The producers needed to know what we
had going on in our lives so they could decide what they wanted to film. Even though reality shows
capture “reality,” there still needs to be a storyline to follow. Filming us watching TV or reading
doesn’t exactly make riveting television. So we would gather around the mansion’s dining room table,
pencils and day planners in hand, listing off our plans and goals for the next few months. The
producers would throw around ideas with us and would eventually let us know what had been
decided: what we would film, when it would be done, and sometimes even how the things we caught
on camera would fit into upcoming plotlines. Every once in a while we would film an activity, not
really knowing where it would end up. Those types of things often ended up in what they called
“Frankenstein episodes.” For example: me buying an exotic bird as a gift for Hef, Kendra consulting a
“pet psychic,” and Bridget taking her dog to get an agent were intercut to create a pet themed episode.
In several of the meetings, I’d campaigned for a Playboy internship under Marilyn Grabowski,
the photo editor at Studio West. I knew this was never an opportunity Hef would give to me
ordinarily, but I thought that if it was something chronicled for the show than he might actually let me
give it a whirl.
At the time, we had already shot two pictorials for the magazine and I absolutely loved being at
the studio. The idea of working on set with the models and being a part of the decision making really
spoke to me—I was desperate for some sort of creative outlet. Marilyn was responsible for coming
up with ideas and themes for shoots, doing the art direction, and choosing the best photos to send to
Playboy’s Chicago offices for layout design. After spending years admiring all of the Playmate proofs
routed through Mary’s office, reading the memos back and forth between editors, and seeing the final
selects for the magazine, I felt like I had developed an eye for the process. On the occasions the
executive producer pitched the idea to Hef he turned it down. (Hef was never in our plotline
brainstorming sessions; he would be consulted afterwards.) No reason was ever relayed back to me
—just that it didn’t get approved. I was too timid to ask Hef about it myself, particularly with the
knowledge that he had already shot it down.
I was so frustrated, always hearing “no, no, no!”
“It’s the one idea I’m really excited about and he keeps turning it down!” I complained to
Bridget one day while I was lounging in her room. Not only was I the quietest, least outgoing cast
member, but my interests overlapped with Bridget’s so much that I found it difficult to find plot ideas
for myself. There were so few things that felt unique to me and were also within the boundaries of
what Hef would let me do. I was starting to lose patience.
As she set about organizing a pile of craft supplies, she told me she had actually heard something
about it. Sitting cross-legged on her poufy pink round bed, she and I had been discussing ideas for the