Down the Rabbit Hole - Holly Madison

period” would come to an abrupt end, so I wanted to make sure I was playing by all the rules. I
chalked it up to a bad mood, but she didn’t seem that excited to have me as a neighbor.
After some coaxing, she finally offered me the rundown:
• Monday was “Manly Night.” Hef would have his guy friends over for a buffet dinner and
a movie in the mansion’s screening room.
• Tuesday was “Family Night.” Hef’s wife and two sons, who lived next door in a house
Hef had purchased for them, would come over to all spend time together.
• Wednesday and Friday were “Club Nights.” We were all expected to be ready by 10 P.M.
to be shuttled off with Hef to exclusive nightclubs all around Los Angeles.
• Thursday (like Monday and Tuesday) was an “Off Night.” While we had the evenings
free to do as we pleased, the girlfriends were still required to be inside mansion walls
by 9 P.M.
• Saturday was a buffet dinner and movie with Hef.
• Sunday was the “Fun in the Sun” pool party during the day and dinner and a movie at
night.
No one gave me a tour of the mansion when I arrived, either. I knew my way around the grounds
and most of the main house, but for weeks I kept discovering new places on the property. There was
an underground secret passage that led from the main house to the gym, which was in the basement
level of the bathhouse. The mansion itself had a large basement, full of employee lockers, storage
closets, and laundry facilities. A panel in the wall of the living room could pop out to reveal a secret
wine cellar, which was used as a speakeasy in the 1920s when the house was built. The master
bedroom had an attic level where Hef kept a personal office, of sorts. The adjacent bathroom truly
looked like a time capsule or the land that time forgot. Gold shag rug covered the floor. A tray of
toiletries from the 1970s sat untouched on the counter. The sink handles were carved to look like
naked ladies.
There was a four-bedroom guesthouse on the grounds that hosted Playmates and Playmate
candidates when they were brought in from out of town to shoot at Playboy Studio West in Santa
Monica. I assumed the Playmate guesthouse would be plush and clean, like a hotel, with perhaps
some Playmate memorabilia strewn about to give it a sense of atmosphere. In reality, the guesthouse
could have been described as “Grandma’s attic meets rent-by-the-hour motel.” In the ’70s, Hef’s
girlfriend Barbi Benton had decorated the guesthouse as a charming early-American cottage, but over
the years the theme fell apart. What was left was dark, dingy, and depressing.
There were many rules to living in the mansion, but most of them I had to figure out on my own.
Like I said, no one handed me The Playboy Mansion for Dummies when I arrived. I also learned that
the other girlfriends weren’t so eager to help out the newbies, since it was in their best interest for us
to stumble around in order to make all of them look better.
First, there was a curfew. For being an older man, Hef stayed up reasonably late (usually tucking
in around 11 P.M.), but he required his girlfriends in by 9 P.M. Apparently, we couldn’t get into too