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 dream come true!
“Do you think I could ever be a Playmate?” I squeaked nervously to Hef, my voice coming out even higher pitched than usual.
I held my breath.
After living at the mansion for quite some time, I finally got up the nerve to ask about the possibility point-blank. I spit the question out one evening while he was reviewing Playmate videos in his room.
“I knew you would eventually ask that,” he replied solemnly, his eyes still focused on the video. Finally he let out a sigh and said, “I don’t think so, Holly. There are a lot of blondes scheduled for upcoming months already.”
A massive lump formed in my throat. Okay, I thought, fighting back the tears. I can take that. It seemed reasonable: too many blondes.
“Besides,” he continued, now looking directly at me. “You don’t have the look. You just don’t photograph well.”
“Oh,” I said slowly, careful to keep my voice from quivering. “Right.” I’d always felt that Hef didn’t think I was very pretty and that he thought I was lucky to be living at the mansion. But hearing him basically say that hurt even worse than I could have imagined. I had prepared myself for a negative response, but I had thought he would have been more tactful. Luckily, his eyes remained riveted on the TV screens, so I could wipe away my tears discreetly.
“I’d let you shoot for ‘Cyber Girl,’ though,” he offered, as if it were some kind of consolation prize. Playboy.com featured a new “Cyber Girl” each week—these were usually just photos pulled from the rejected Playmate test shoots. It was a throwaway offer. He knew it; I knew it, and I wasn’t interested in being one of the many girls haphazardly tossed online without ceremony. If I was going to take the leap and pose nude for the world to see, I wanted to become Playmate of the Month.
But then I thought, maybe posing for a “Cyber Girl” shoot would show Hef that he was wrong about me. Perhaps the photos would actually turn out good enough that he’d have to reconsider me for Playmate. On the other hand, if the photos were a total disaster, maybe all those flaws that he saw in me were real and I’d finally be forced to face them dead-on. Was I so hideous that I couldn’t be a Playmate?
“OKAY, OPEN YOUR KNEES a little wider,” directed the photographer, as I sat facing the camera on a red sofa without a stitch of clothing on my body.
The shoot took place at the Bunny House—the brightly colored midcentury home right across the street from the mansion. Naturally, I was a bit anxious, but Sarah the makeup artist (who has since become a good friend) made me feel at ease. The photographers were tired of the heavy-handed, ’90s-style makeup Hef still liked on Playmates. Since this was not a Playmate shoot, they took the opportunity to use a more natural style, which I ended up liking.
When the stylists wheeled in the wardrobe options on a metal clothing rack, my stomach tied itself in knots. As Hef’s main girlfriend, they wanted me in a short satin kimono robe touting a plastic prop pipe (say that three times fast!) to pay homage to my boyfriend (the Hef tribute had been done once before by his second wife, Kimberley, and would be done again by his third wife, Crystal). The remaining selections felt more downscale stripper than the old Hollywood glamour style that I would have preferred.
“Can’t you see too much?” I asked timidly. This was Playboy, I thought. Not Hustler.
“No, you can’t see anything from this angle if you lean forward,” the photographer reassured. “I swear.”
The photographer assigned wasn’t one of the two used to shoot the Playmate pictorials, and I was worried that I was wasting my time. Since I wasn’t getting the opportunity to shoot with the best of the best, I was terrified that my photos weren’t going to be the home run I had hoped they would be. Despite what my gut was telling me, I continued with the shoot. I didn’t want to seem ungrateful or bratty.
“How did the shoot go?” Hef asked when I appeared in the master bedroom. After a long day (which included a car wash scene, in February) I was cold and exhausted and wanted nothing more than to shower and crawl into my pajamas.
“I’m not sure,” I answered honestly. “I don’t know if I’ll like the photos.”
When the slides came back (Playboy was still shooting on film in 2003), I hated them. As I predicted, they were far more explicit than I wanted them to be. I felt like a fool for listening to that photographer.
Adding insult to injury, the slides were accompanied by a memo from Playboy’s Chicago photo editor, saying something to the effect of: “Hef, do you want us to use these? They look like they were shot in your room with her wearing your robe and smoking your pipe.”
The comment made it sound like I was some interloper sneaking around the Playboy Mansion taking photos without permission. Was the editor not aware that I was Hef’s girlfriend? I felt so embarrassed. Usually, Hef made such a public fuss over whoever his main girlfriend was—I felt like I was the first one he neglected to do that with. It made me feel like I was not beautiful or glamorous enough to merit such praise. In hindsight, I know he was just sick of the high turnover with his past girlfriends. They were lasting, on average, about six months, and he was done floating any girl’s ego. He had come to the conclusion that if he kept us broken and needy, we would stay.
Broken and needy were definitely two adjectives that perfectly described me during that time. After about a year of stubbornly trying to maintain some semblance of individuality, I finally gave up on my short hair and started wearing clip-in extensions to give me the long hair Hef preferred. I was feeling more disconnected than ever from the goals I once had; mansion life had eaten away at my self-esteem. I found myself constantly trying to compete with the other girlfriends who were all caught up in who was prettiest. It was a perpetual contest to see who could be the skinniest, tannest, bustiest, most baby-faced with the longest, whitest hair.
We were all striving to win. We were trying so hard to stand out and be coined the “hottest” of Hef’s harem that we completely missed the fact that we were making ourselves indistinguishable from one another.
After thinking about it for a few days, I finally worked up the courage to ask Hef to scrap my Cyber Girl shoot. With a huge knot in my stomach I explained that I wasn’t really comfortable with the results and would rather the photos weren’t floating around the Internet. He assured me that he would let the Chicago
office know—and he did, but only after the pictures had already been posted on Playboy.com for a few hours. The editor took them down immediately, but that doesn’t mean much. Once something appears on the Internet, it never really goes away. To this day, those photos are probably floating around somewhere.
Oh well, I thought. I guess there could be worse things out there.
WHILE I WAS RACKING up disappointment after disappointment in the pursuit of a career, my “social life” at the mansion wasn’t faring any better.
Most of the other girlfriends seemed to hate me with a passion, though I never did anything to them besides keep my distance. Daphne was the alpha female of that group and the other girls followed her like sheep. It didn’t take a genius to figure out that Daphne would have loved to install Dianna in my place as main girlfriend. They felt my role as main girlfriend was to be a sort of representative for the other girls and make sure that we continued to enjoy all the perks of living at the mansion. Under their breath, when they weren’t making comments about my appearance (Daphne loved to make fun of my “thin lips” since I was one of the few who didn’t have my pout inflated with fillers), I’d overhear them make comments alluding to the fact that I didn’t “run things” as well as Tina, since Hef had so noticeably tightened his purse strings with the girlfriends in the last few years.
The majority of the women who had done time at the mansion were born hustlers who knew how to milk a man for every last cent. That ability to manipulate just wasn’t a part of my DNA. I was way too timid, and besides, I actually liked Hef. I wasn’t interested in scamming every penny I could get out of him! Prior to me, Hef’s girlfriends were masters of the hustle.
The Bentley twins were showered in lavish gifts: Rolex watches, fur coats, matching BMWs, designer gowns, and even furniture for their off-property apartments (which were also paid for by Hef). When the twins (along with Brande Roderick) moved out, the original seven moved in and Hef decided to tighten up the purse strings. Still, Tina was skillfully calculating and was able to secure each girlfriend a leased car, a sizable wardrobe allowance, and lavish Christmas gifts. But it was nothing on the scale of what the twins had managed to bank.
When Tina left the mansion, Hef tightened his belt even further: no shopping sprees, less allowance, and off-site apartments were now strictly forbidden.
Anyone who joined the Playboy harem was after something. Most of the girlfriends were looking to get their pictorial and as much cash as humanly possible, like hookers on the clock. While I wasn’t after Hef’s money (I was just grateful to have a roof over my head!), I too saw my stay at the mansion as a once-in-a-lifetime sort of thing that could lead to potential opportunities for my future.
“I don’t care about money, I just want to be wonderful,” was a Marilyn Monroe quote I lived by. I wasn’t looking to get rich, but I was hungry for a career. I just wanted to accomplish something . . . anything! Sure, I believed I had come to care for Hef, but let’s get real: it wasn’t love at first sight and I had my own set of goals. Greed just wasn’t part of it.
During a trip to New York City for Playboy’s 50th Anniversary Party (one of many anniversary parties that would be held that year), Bridget, Amber, and I were excited to spend a few days touring the city in style! While Hef busied himself with press interviews, we spent time visiting Central Park, ice-skating in Rockefeller Center, eating New York–style pizza, and jumping on the giant keyboard at the FAO Schwarz on Fifth Avenue.
As required, we invited the Mean Girls to join us, but they couldn’t be bothered. Instead, they ran off to Bergdorf’s and purchased three incredibly expensive designer handbags. Though Hef threw a fit about the purchase, he let them keep the bags.
While Bridget, Amber, and I were focused on the experiences and actually liked some things about Hef and his lifestyle, the Mean Girls seemed to be focused only on the money. It felt like each side thought the other side prevented them from getting what they wanted. Knowing damn well what the previous roster of girls had been given, it seemed the girlfriends decided I was the reason their pockets weren’t lined with cash and jewelry and decided to take matters into their own hands.
“Holly, Hef would like to see you in his office,” the secretary said through the phone line. The Mean Girls made sure I was routinely called down to the principal’s office, so to speak.
What was it this time? I thought. One girl in particular loved to whip up fictional stories about how I had supposedly wronged her. Any time she would get heat from Hef for not following his rules to a T (this happened constantly with most of the girlfriends), she loved to deflect attention from herself by making something up about me. Every time she made a mistake, it was somehow my fault, though we had virtually nothing to do with each other. It was all bullshit. Hef saw through her. After all, she wasn’t that clever, but he loved playing the game too much to call her out on her lies. Being able to hold her stories over my head was just another tool Hef used to manipulate me. Watching me get upset and squirm was just another way he satisfied his perversions.
Every year since I had moved into the mansion, I made a trip to Disneyland for my birthday. I expected all of the girlfriends to attend—simply because girlfriends were required to attend all planned events on Hef’s schedule—but only Bridget, Amber, and my friend Britney showed up. The message was received loud and clear: I was being boycotted. They were trying to convince Hef that things would be better if I weren’t around, because, after all, he was constantly saying that he just wanted “harmony” among the girls.
I don’t believe that he really wanted harmony—not for a single minute. He thrived on catty drama among the women. Nothing made him feel more important than a bunch of girls “fighting over him.” At the time, though, we were all naïve enough to believe what he told us.
Unfortunately for the Mean Girls, their Disneyland boycott backfired. Not only did it make them look like pouty little children, which Hef hated, but it also allowed me to have the most enjoyable birthday celebration I’d had in a while!
They wouldn’t give up that easily, though.
In an attempt to further drive their point home, they had all gone out to the Santa Monica Pier together and had a group caricature done for Hef as a gift.
“Knock, knock!” one of the girls squealed loudly through the master bedroom door. Hef and I were sitting in bed eating dinner and watching the news, as we usually did on weeknights, when the Mean Girls came in to present him with the gift. As he fawned and cooed over the picture, I noticed the girls exchange a few sly glances and smirks. It was as if they were saying: “See how great we all look . . . without Holly and Bridget.”
If Bridget or I had chosen to get a gift for Hef without including the other girlfriends, we would have been reprimanded for not including everyone. Yet no one—Hef included—acknowledged my presence in the room or my glaring omission from the drawing. It was as if I were a ghost.
What Daphne and Dianna didn’t realize is that they’d never be able to push Bridget and me out as long as they were still aligned with Elizabeth and Whitney. Shrill Elizabeth and “pushy” Whitney were never Hef’s cup of tea. I heard he turned each of them down the first time they had asked to move in, but eventually he kept them around as filler—so he could reach the “seven girlfriends” quota that had become his trademark. (Over the previous year or so, since his girlfriends hadn’t been gracing the pages of the magazine as often as they once did, the number of girls clamoring to be included in his “party posse” had understandably subsided.)
Whitney had always been Hef’s least favorite—in part because she came into the group under some unsavory circumstances.
“Hef, do you think Whitney could start getting an allowance?” Tina had asked. Despite having left the mansion months earlier, Tina still trotted around from time to time to see what she could squeeze out of Hef. “She works really hard to get all dressed up for you and to come to all the events. She’d make a really great girlfriend.”
&n
bsp; At the time, Whitney was good enough to join him in the bedroom, but he wasn’t too keen on asking her to move in. Tina had clearly been recruited to go to bat for her.
“Actually, Tina, I’m hoping that with this next set of girls, expectations won’t be so high,” Hef explained to his former girlfriend. “Do you know I spent two million dollars just on girlfriends and trips in the past few years?” (Most of that went towards the private planes he chartered, sometimes on the company tab, and the trips he took his girlfriends on—including a lavish European tour before I had arrived.)
“She’s putting in all this time and all she’s getting out of it is a drink and a fuck!” Tina said, clearly frustrated that she wasn’t getting her way. Like I said, this girl was a hustler.
God, I thought. I could never get away with talking to Hef like that.
The room got very silent as Hef sat staring at Tina.
“I like to think of this as all of their dreams coming true,” he said very solemnly. Even Tina was struck silent by how serious he was. Did he really mean what he was saying? It sounded so conceited to assume that simply being in his presence (or bedroom) was a “dream come true” for these women. The “hurt” expression he held on his face forced Tina to abort her mission.
“Okay, sorry,” Tina offered and leaned over to give him a peck on the mouth. As she walked out the door, she called out a thoughtless “Love you!”
For months Hef continued to reject Whitney’s pleas to become a girlfriend, but eventually her persistence paid off and one day she moved into the mansion. We quickly discovered she was a pathological liar—and it was actually pretty amusing. Her age, former professions, and life story changed daily.
“Darlin’?” Hef asked, appearing in my dressing area one afternoon.
“Yes?” I asked, pulling my nose out of my French homework.
“I need to talk to you about something,” he said, his brows furrowed, and pulled up my vanity stool. His somber eyes connected with mine. “Did you drug Whitney’s drink last night?”
Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny Page 13
