Down the Rabbit Hole - Holly Madison

acquiesced.
Wow, I thought. I was familiar with America’s Next Top Model, the show that this Playmate
competition show appeared to be based on, and never would have guessed that contestants were kept
on strictly to stir the pot. It made sense, but in the early days of reality TV, viewers weren’t as wise
to the process as they are now.
Interestingly enough, the girl Hef had deemed “overweight” became a favorite of a Playboy
photo editor, and her centerfold was so well produced, Hef ended up selecting it as the winner. Since
viewers wouldn’t be happy with an antagonist winning the competition, the show was quickly reedited
to take out those “pot-stirring bitch” moments and make the winner look like America’s
Sweetheart. (By the way, I always found the winner to be a nice person. I suppose she was a little
more honest and blunt than the rest of the contestants, hence the “bitch” label that people like to throw
onto assertive women.)
Anything is possible, I thought. Maybe Hef will one day change his mind about my chances of
being a centerfold, too.
The television special was just the latest in a slew of media opportunities Hef had begun
participating in over the past few years. Two of the most substantial, documentaries titled Playboy:
The Party Continues (2000) and Inside the Playboy Mansion (filmed before my arrival in 2001),
followed Hef’s new life as a 70-something swinger. Any time a Playboy-related program aired, it
scored fantastic ratings. Middle America was still buying into the intrigue and racy glamour of the
Playboy world, made interesting again by Hef’s reemergence onto the social scene.
Hef loved the documentaries that covered his life, but he also loved any chance to cross over to
a younger audience (he was obsessed with appearing “hip” and relevant), which is how we found
ourselves doing press in the middle of a Justin Timberlake video shoot in the mansion’s backyard.
“So, do you listen to hip-hop?” the MTV reporter asked.
“Uhhh,” Hef began, seemingly at a loss for words. “Ummm . . .”
In early 2003, Justin Timberlake was at the top of his game. You couldn’t spend more than 10
minutes at any nightclub in Los Angeles before hearing a track from his latest album Justified (so
much so that I still can’t listen to a single song without being overcome by painful memories). When a
request came through Playboy asking to shoot a music video at the mansion for the Nelly track “Work
It” featuring Justin Timberlake, the answer was of course yes.
When it came time to shoot the video, the director offered Hef and his girlfriends small roles.
Because some of the other models in the video were topless, it was deemed too racy for the United
States and only aired internationally. During the shoot, Hef sat in his own wooden throne-like chair
bobbing along to the beat and wearing black sunglasses, with Nelly and Justin Timberlake on either
side of him, while we danced around them in skimpy outfits. After filming wrapped, Hef was asked to
do an interview with MTV news. All the girlfriends gathered around Hef, and I took my place at his
immediate right.
“Uhhh,” Hef continued to fumble. This nonresponse was completely out of the ordinary. Usually
he was a pro at these interviews, able to call upon a laundry list of canned responses to just about any
question you can imagine. I listened to Hef rattle off the same answers he’d given a million times