Down the Rabbit Hole - Holly Madison

Vegas where they were readying the new Playboy Club, set to open the following year. Knowing
what a fan I was of the Bunny costume and of Roberto Cavalli (who had designed the new Bunny
ensembles for the club), Playboy PR tapped me to model one of the new prototypes in a fashion show
(along with several Playmates). Not only was I able to wear this amazing costume, but I was able to
do it without the other two girlfriends. It was one of those small instances where I could feel like I
was my own person. I savored the moment and it became one of my all-time favorite episodes.
Less than a year after our first magazine appearance, Hef ordered our second pictorial and cover
for the September 2006 issue. The cover would be on stands as season two premiered—and I even
got to develop the concept! I sketched the idea out on a cocktail napkin while at a Dodgers game.
Taking the notion of “the girl next door” literally, the cover showed the three of us peeking through a
white window with frilly drapes—and it became the first time the magazine photographed a
corresponding back cover (which, naturally, was a view of our butts as we were peeking out the
window). Both images were shot simultaneously to ensure continuity. And while this time we were
finally able to star in individually themed shoots, it was mandated that the other two girls appear in
the background of each. We still felt frustrated that Hef seemed to think we were only worthwhile as
a threesome, but it turned out that casting us as a team wasn’t making us jealous and turning us against
each other; instead it was turning us into a team in real life.
Just like the first shoot, we had a blast modeling together. Being in the magazine was a dream
come true for all of us, so being able to do it again was icing on the cake. But just like the first time
around, Bridget’s emotions started to get the better of her. She began to feel like the photo editor,
Marilyn, was singling her out and nitpicking every detail. If there was a hair out of place, it was
Bridget’s. If someone needed to move, it was Bridget. It kept up like this for most of the shoot.
Eventually Bridget reached a breaking point and needed to take a moment in the makeup room.
Surprisingly, Kendra went in to comfort her and put her in a better mood. I couldn’t have imagined
that happening a year earlier, when things had been more strained between the three of us. We had
made huge progress with our friendships.
Other changes were afoot as well. Prior to the show, we’d almost never traveled—Hef was a
creature of habit who despised any sort of variation from his routine. Once he finds a comfortable
one, he’s bound to stick with it for at least the next few decades. So when we learned that the second
season would see us not only on multiple trips to Las Vegas, but also on a two-week-long European
getaway, we were flabbergasted. Paris, London, Cannes, Barcelona, Munich, Rome . . . for us, it was
unheard of!
It was on these trips that Bridget and I finally found something we had in common with Kendra:
we all loved sightseeing. The three of us were very different, but we all came from working-class
backgrounds. I think at one point we each believed that moving into the mansion would give us the
opportunity to see the world, but the truth is, we rarely left our neighborhood. After a while, we gave
up hope that we would ever travel. Now that Hef knew the world was watching, he had to be the
“playboy” everyone believed he was. We were finally getting the experience we thought we had
signed up for!
It was the opportunity of a lifetime, to be able to travel around the world in style, so we didn’t