Down the Rabbit Hole - Holly Madison

would have thought Hugh Hefner preferred his girlfriends sexy and retro, but his taste was
surprisingly . . . well, cheap. As for Tina and Hef, they would never arrive until everyone was
already in place—like some antiquated nod to the hierarchy that existed.
One of the butlers arranged us in the hall and snapped a few pictures for Hef’s scrapbook before
we piled into the limousine—another Playboy tradition to satisfy Hef’s endless desire for mementos
(the next morning prints would be placed outside each girl’s bedroom door, which only amplified the
massive pressure to always look perfect and caused the girlfriends to spend hours critiquing their
appearances).
When we finally arrived in Hollywood, the scene outside of the nightclub was absolute chaos.
Hundreds of men in Von Dutch trucker hats and women in their obligatory low-rise Frankie B. jeans
and fedoras (because in 2001 every club girl was just dying to be mistaken for Britney Spears) were
bombarding the entryway, clamoring over one another to get the attention of the resident doormen
stationed behind the red velvet rope. From the looks of it, you would have thought Oprah was inside
giving away free cars. As the limo door opened, four security guards rushed to part the sea of clubgoers
so we could make our way inside. I had been to nightclubs before, but I was usually one of
those unlucky souls not “on the list” and relegated to the milelong line that wrapped around the block.
I was one of the first to step out of the limo and every set of eyes turned to check if I was someone
worth knowing. I started fussing with my top, unnerved by this unexpected attention. One by one, each
bottle blonde piled out of the limousine—waiting for Hef before we made our way inside. Vicky must
have noticed the astonishment in my eyes because she leaned over and whispered, “ ’NSYNC and
Christina Aguilera were here the last time we came.”
When Hef finally emerged from the car, the crowd went wild. People were shouting his name
and shoving one another to get a better look. He lifted a hand to wave to the crowd as if he were some
kind of dignitary. The whole thing seemed incredibly strange to me, but for Hef it had become a
regular part of his weekly routine on the L.A. club scene. For decades, Hef was an infamous
homebody. After all, he created his own version of paradise at the Playboy Mansion, so why would
he ever want to leave? Throughout the ’70s, ’80s, and ’90s, it was extremely rare to see him out and
about. In 1999, when he separated from his wife of almost 10 years, Kimberley Conrad, a few of his
friends persuaded him to leave his compound for a night on the town. What happened next was a
surprise to everyone. People went absolutely crazy to see this 70-something icon from another era at
an L.A. nightclub. Shortly thereafter Hef instituted his biweekly club nights. Rolling Stone magazine
called it “Hugh Hefner’s Resurrection.” (I would later learn that this sort of behavior wasn’t atypical.
The only thing Hef loved more than the mansion was himself. The sort of super fandom he saw at
these nightclubs was all the fuel this senior citizen needed to keep painting the town red.)
It was during one such evening, after his separation, that Hef met Sandy and Mandy Bentley.
Immediately he began dating these two blond bombshells, along with another blonde, Brande
Roderick. This unusual foursome made Hef even more of a sensation. The age difference, the number
of girlfriends, the hint of incest, the fact that all three of the girls’ names rhymed, along with Hef’s
constant public insistence that he had to take Viagra to keep up with all of these women made the
situation truly bizarre. In Los Angeles the bizarre is often appreciated, if only momentarily, and at that