Down the Rabbit Hole - Holly Madison

After a short time in the city, I settled into a tiny Westwood apartment with my friend Nora.
Besides a mattress, a lamp, and a pile of schoolbooks, my room was all but empty. My Hooters salary
was barely covering my daily expenses, so I relied heavily on scholarships in order to pay for a
portion of the hefty tuition at the private university. What was left over for me to pay? . . . Well, let’s
just say it went unpaid for quite some time.
I was 20 years old and almost delusionally confident and optimistic. I was convinced I could do
anything I could put my mind to . . . even become a famous actress and get my college degree within a
few years. I knew I wasn’t always the hottest girl in the room, but I also knew I wanted success so
badly that I would work harder than anyone else for it. For a while, I did manage to juggle it all: the
school, the job, and the auditions. There was only so much longer I could keep up it up, though. I was
burning the candle at both ends and something was bound to give.
As it happens with transfers, many of my credits from Portland State didn’t apply towards my
program at Loyola Marymount. In order to graduate on time, I’d have to load up on credits, which
included long theater hours that would require working backstage on different productions during the
evenings when I typically waitressed. I knew that with a packed school schedule and a full-time job, I
wouldn’t have any time to study. And if I couldn’t study, I wouldn’t be able to meet the minimum
grade requirements of my scholarships. So after a year at LMU, I decided to take a break from school
to focus on pursuing my career. I would never be as young or as eager as I was in that moment, and I
figured that I might as well take the plunge. School would always be there, so if it didn’t work out for
me, I could easily go back and finish my degree. It’s not unusual to graduate from college at 30; but
it’s a lot less likely to break into acting at that age. In my heart, I thought it was the best decision for
me at the time.
With school on hold, I picked up more shifts at Hooters and eventually started working part time
as a Hawaiian Tropic model. The gig basically required me to show up at events in company apparel
or appear in movie bit roles in swimwear and a “Miss Hawaiian Tropic” pageant sash. I thought it
would be a great way to make extra money and also to meet people. In Hollywood, you never knew
where opportunities would arise. I would end up being right, of course. The gig would lead to
something, though maybe not what I had expected.
Not long after, at a Hawaiian Tropic Bikini Contest in Beverly Hills, one of the event organizers
pointed out an older man.
“You see that guy over there?” he asked. “That’s Hugh Hefner’s personal physician.” Naturally,
it was exciting that someone associated was Playboy was at the event, but I didn’t give it too much
consideration until an hour later when the man approached me.
“Would you be interested in attending a party at the Playboy Mansion?” he said, barely taking
the time to meet my eyes. My mouth fell to the floor. He posed the remark as a question, but it was
clear he already knew there was only one answer.
He’d apparently been at the party offering invitations to the girls he deemed Playboy-party
worthy. It wasn’t abnormal for a representative from the magazine or one of Hef’s friends to invite
attractive women to the parties. Many of my coworkers had become regulars at the mansion. I guess I
just wasn’t expecting an invitation of my own, and especially not from his doctor of all people.