Down the Rabbit Hole - Holly Madison

fortune. Boy, was I wrong. There have been more than 720 Playmates in Playboy’s history. How
many of them can you name? Even if I did happen to score a pictorial someday, it didn’t necessarily
mean anything beyond validation. More than ever, I had begun to accept that I would never achieve
anything greater than my role as “Hef’s main girlfriend.”
The handful of Playmates who had become famous were all in attendance that night. Playmate
and TV personality Jenny McCarthy hosted the event (her beauty is matched by her wit—she ended up
being the best part of the show, by far!), which included musical numbers and stand-up acts. Nineties
Playmate stars Anna Nicole Smith and Pamela Anderson were also in attendance.
Barbi Benton, Hef’s main girlfriend in the ’60s and ’70s, attended the soiree. While not
technically a Playmate, Barbi was featured in several pictorials and on four Playboy covers. Hef
went out of his way to keep in touch with many of his ex-girlfriends—partly out of sentimentality but
also, I believe, as a form of damage control. Keeping in the good graces of his ex-girlfriends was a
sort of insurance policy. I guess he figured the regular invites back to the mansion would keep anyone
from speaking negatively about him.
Barbi would end up becoming a regular guest star on The Girls Next Door, and I ended up really
liking her. She was quirky, friendly, and creative. Barbi wasn’t a close confidant, though. Despite
having dated the same man, we couldn’t really relate on that subject. Sure, Hef was much older than
she was when they dated—old enough to be her father, though, not her grandfather. Plus, Barbi didn’t
have to share Hef publicly. He wasn’t faithful to her by any means, but she could at least pretend the
other women didn’t exist. Never was she forced to one side or the other to make room for a gaggle of
giggling blondes to line up around him.
It was a surprise to me how mannered and reserved many of the former Playmates were. Despite
presenting Hef with a birthday cake totally nude while filming an episode of Girls Next Door, Pam
Anderson always struck me as incredibly guarded and quite shy. Spending a decade being chased by
paparazzi must have made her cautious around people. Like Pam, Anna Nicole was surprisingly quiet
and very polite. I met the towering blonde only briefly, but she exuded the charm and etiquette of a
real southern belle. Like most former Playmates, they were cordial with Hef, but I don’t believe they
knew him very well. During the Pam/Anna Nicole era, he was married to Kimberley and didn’t
socialize with the Playmates much (if at all). Needless to say, those Playmates didn’t have to endure
the Playboy “casting couch” that existed after the end of his marriage.
I was beyond thrilled to meet 1950s pinup Bettie Page—a living legend! While her hair had long
ago turned gray, she still wore it neatly styled with those short iconic bangs. In her later years, Bettie
became a born-again Christian and conducted herself like the gentle, churchgoing lady she was. Her
name and likeness had become popular again in the ’90s, and it was Hef and his friend Mark Roesler
who found Bettie and reconnected her with the business end of her pinup past. As a small memento, I
gave Bettie a “Miss January” necklace to commemorate her January 1955 centerfold. She later told
me she hung it on her wall so she could always “look at it.” When she passed away in 2008, I was
heartbroken but grateful that we were able to have met.
Despite the odds, a part of me still held on to my dream of one day becoming a famous Playboy
Playmate. And after meeting these iconic women that night, I felt like I should at least try to make my