Down the Rabbit Hole - Holly Madison

Just then, Hef appeared next to me. Seacrest had arrived and network execs and upper
management were clamoring for his attention. Earlier that year, Seacrest agreed to a hyper-lucrative
megadeal with the network and was quickly christened E!’s resident Golden Boy.
Hef grumbled under his breath, something about how E! would never have been able to afford
Ryan if GND hadn’t been so successful, before shuffling off towards a nearby table, expecting me to
follow.
Hef had become obsessed with the show. When GND was first ordered, he wasn’t particularly
eager to make many appearances.
“This way, Daddy doesn’t have to do the work!” he guffawed at the press when they would ask
him why he decided to do a reality show that centered around his girlfriends. He also described
reality shows as “dumb and a waste of time.”
His tune changed as soon as he realized just how popular the show had become. Suddenly it
became imperative that Hef have a substantial scene in every episode. If he saw a rough cut of an
episode and wasn’t happy with the amount of screen time he was getting, we were called back to refilm
scenes in a manner that would include him more. Even when we shot entire episodes off the
mansion grounds, we were obligated to call home on camera, so the show could cut back to what Hef
was doing back at the mansion. Not surprisingly, it usually involved him spending time with other
women. At the end of the day, the producers were right. It was Hef’s show.
By the time we began filming on season three, my attitude changed when it came to our little
reality program: I was finally fully embracing it. I had been skeptical of how the series would affect
my life. But by the time the network ordered a third season, even I had to admit that we had a hit on
our hands. I started to see the show as an opportunity. It was an excuse to travel, to go outside the
mansion gates and try new things. Also, I was starting to realize that being on a reality show brings a
little magic with it. People are more willing to give you a chance when you are on TV, even if it’s on
the silliest of reality shows. I was beginning to sense that I might be able to get something bigger out
of this, even if that something was confined to the world of Playboy.
That season, we were finally able to film in December and capture my birthday (Kendra’s and
Bridget’s birthdays had both been covered twice over the previous two seasons). Birthday episodes
were important to each of us, because it was another opportunity to feel special and to be portrayed
as individuals. I think being able to feel like our own person from time to time made us all feel a little
less insecure, which allowed us to come together as friends more and more. Even a silly activity like
horseback riding helped us bond and, indirectly, ended up having a big influence on my life.
The show’s producers found Sunset Ranch in the Hollywood Hills, offering horseback rides
over the hills into Burbank and back to Hollywood. For the episode called “May the Horse Be with
You” we drove up Beachwood Drive and passed through an old stone gateway into a quiet area
populated with adorable storybook-style cottages. I had never seen houses so cute. They looked like
one of the seven dwarves was going to pop out of one of the doors at any given moment.
What is this place? I thought.
I would later learn that the area was developed as a community called Hollywoodland (that’s
where the famous Hollywood sign comes from) and each house was built to look as if it came straight