Down the Rabbit Hole - Holly Madison

CHAPTER 4
“Now, here, you see, it takes all the running you can do, to keep in the same
place. If you want to get somewhere else, you must run at least twice as fast as
that!”
—Lewis Carroll, Through the Looking-Glass
You girls are basically Hef’s traveling harem, right?” asked the eager New York magazine reporter,
sticking a small silver voice recorder in my face.
Only a few weeks after I had moved into the mansion, Hef whisked us away on a trip to New
York City for his Comedy Central’s Friars Club Roast. I’d never been to New York before; I’d
actually never been off the West Coast before. It seemed so surreal—and slightly absurd—that a
reporter would be questioning me about my life with Hugh Hefner.
“Umm,” I began, through a short laugh. I wasn’t quite sure how to respond to this older,
bespectacled journalist with the practical brown bob. Despite what the nature of the event may
suggest, I couldn’t be certain if she was joking or not.
This particular roast had special meaning to New Yorkers. In the wake of the September 11
tragedy, a dark cloud hovered over New York—and the entire country for that matter. Comedy
Central reasoned that giving people an hour of time to laugh again might help kick-start the healing
process, and they decided to move forward with Hef’s scheduled roast.
The day before the event, Hef, his girlfriends, and his staff (including his longtime assistant
Mary O’Connor, his personal photographer, and a team of security) boarded a chartered private jet at
Van Nuys airport and headed to New York. The network hosted us at the New York Hilton Midtown.
Hef and Tina occupied the hotel’s regal presidential suite while the rest of us were given gorgeous
rooms with breathtaking views of the city.
Whose life was I living? Private jets! Luxury hotels! Last month I was barely making rent on a
shitty shared apartment. There were many perks to being one of Hugh Hefner’s girlfriends, including
the VIP treatment everywhere we went. I’ll be honest, being treated like royalty wasn’t necessarily a
hard routine to fall into. Sure, it was mainly directed at Hef and we were considered ornamental, but
reaping the benefits of his celebrity certainly had its moments.
Prior to the festivities, Hef was expected to walk the red carpet with his seven girlfriends for
brief press interviews and to pose for photographers. The attire was black tie, so each girlfriend
packed her most glamorous cocktail dress or pantsuit. With my clothing allowance I was able to buy a