Down the Rabbit Hole - Holly Madison

girls wanted to get caught on tape. By the next afternoon, Hef’s video department would have a tape
sitting outside Hef’s door with a “highlight reel” from the last night’s party, copies of which would be
sent to local news stations. So much for “what happens at the mansion stays at the mansion!”
That year, Playboy would collaborate with Girls Gone Wild to release a DVD titled Playboy
Mansion Parties Uncensored. The DVD—a compilation of all kinds of random party footage,
including nudity and celebrity sightings—flew off the shelves. The effect that particular business
venture had on the brand was questionable, however. The overeagerness of Playboy to exploit what
went on at the mansion parties dirtied the cachet of these events that were once considered exclusive
and glamorous. No longer feeling like their privacy was being respected, fewer and fewer A-list
celebrities wanted to attend anymore. Understandably so.
The night ended with me passed out on my bedroom floor with a cheeseburger in my lap. It had
become clear to me that being a part of Hugh Hefner’s “party posse” wasn’t as glamorous as it
seemed. This was a far cry from what I pictured life here would be like when I first laid eyes on the
gorgeous Bentley twins a year and a half earlier at the Midsummer Night’s Dream Party. The situation
was also much lonelier than I could have ever imagined. Not to mention more stressful.
The day-to-day stress of mansion life had taken such a toll on me that I could feel myself
mentally regressing. My memory started to dull—and things I used to know with certainty started to
fade from my mind. I’ve always considered myself an intelligent girl, but I could feel myself getting
dumber and began second-guessing everything. That might sound insane, but I suppose you are the
company you keep . . . and let’s just say the other six girlfriends weren’t necessarily winning any
spelling bees.
I was so constantly on edge that I eventually developed a stammer when speaking, so I tried as
best I could to stay quiet and not risk the embarrassment of tripping over sentences.
To Hef, my shrinking violet personality was a sign of submission that he used to manipulate the
other women. It helped my rise through the girlfriend ranks to become among Hef’s favorites.
Over time, I convinced myself that I did actually care for this man . . . that I wanted to be in a
relationship with him despite the fact that I didn’t really know him. Of course, living with someone,
you learn things about their personalities, their tics and their annoyances, but Hef and I never really
talked . . . not about things that mattered. There were no deep conversations or romance between us.
As far as his girlfriends were concerned, we were better seen and not heard. His friends were
there for his intellectual stimulation; my job was to show up and look pretty. Even our daily dialogue
was superficial. If ever I tried to speak to him about books, politics, or world events, he would scoff
at whatever I said. It didn’t matter if my remark was educated or even correct, because if I said it, it
must be wrong. During movie nights, he would lean over to me to explain plotlines and time periods
in the most condescending of ways. Oftentimes I would have to bite my tongue. It was all I could do
to keep from screaming: “I know!” Clearly he was used to, or preferred, a woman with no more than
a grade school level education.
But I was young and blinded by his fame and accomplishments. What wasn’t to love about Hef?
I told myself. Because of his generosity, I was living on this gorgeous estate, attending swanky
Hollywood parties, and had money to spend on clothes, shoes, hair, and makeup. So I reasoned with