Authors: Izabella St. James
As for celebrities, I have seen many go in and ogle but not dare get in. I can’t blame them; as soon as they dip their big toe in the water, the tabloids will be reporting the wild orgy they participated in. And this I know from experience. When Emma visited her mother country—jolly old England, where I am told they love the gossip—she decided to make some pocket change and gave an interview about life at the Mansion. She told the story of how Justin Timberlake got into the Grotto and partied with several naked girls as Cameron Diaz watched. The real story—as I mentioned previously—is quite different. Let me begin by saying that Cameron Diaz was not even there when he was, and this was before they started dating. Emma had a major crush on Mr. JT, so all night we talked to him and his pal, who suggested we all go in the Grotto. Of course we pursued the idea; hey, if there was any chance of getting JT in the Grotto, we were going to try. As the night progressed, JT’s pal did end up going to the Grotto with a couple of girls, but Mr. JT remained fully clothed in his memorable “Who’s afraid of a little pussy” T-shirt. If my own gal pal can exaggerate the truth, many more can and do. Emma’s tabloid feature led to a major fight within the group, and Emma almost got kicked out. After being pressured by Holly to kick her out, Hef came to me and asked me what I thought he should do about Emma, and I saved her butt. I told him it was something we could move past, and hopefully she wouldn’t do anything like that in the future.
My own personal experiences in the Grotto left much to be desired. There I was, a twenty-six-year-old red-blooded American (well, Canadian) girl who enjoyed sex. And the Playboy Mansion, more than anywhere else, is the House that Sex Built. The Grotto for me was Emma, myself, and a few Coronas on a regular week night ... fantasizing about what we would love to do in the Grotto. It’s really sad if you think about it: two young girls, getting drunk, wishing there were some boys around. When we got desperate for male attention, we would call the pantry and order more drinks to be delivered to the Grotto just so we could splash and tease the butler. Desperate times called for desperate measures!
During the entire time I lived at the Mansion, Hef went to the Grotto three times. And unfortunately, or fortunately, for me, I missed all three of those times. The first time, after the usual Friday night out (I stayed in sick) and heavy drinking, the girls managed to convince Hef to go to the Grotto. According to the report I received in the morning, Hef remained sitting while having sex with Holly and Bridget, as the other girls provided visual stimulation by splashing around and touching themselves and each other. It was short-lived; I don’t think Hef can remain in the hot waters of the Grotto for too long because of his heart (he had a stroke in the 1980s), and that is why the Grotto excursions were so infrequent. The other two times happened right before we (Emma, Susan, and I) left the Mansion. It was part of Holly and Bridget’s master plan to exclude us and show Hef what a wild time they could give him without us. So along with the new recruit, eighteen-year-old Kendra, they snuck down there and did what they did.
For me, though, the Grotto remains an elusive fantasy.
15: House Parties.
“No party is any fun unless seasoned with folly.”
—Desiderius Erasmus
W
ho doesn’t like a good party? Parties at the Playboy Mansion were a lot of fun. Hef spends more than a million dollars a year to entertain his guests and himself. The Mansion was always transformed into a magical place according to the theme of the party. Many people would work day and night to get the place ready, and the transformation was incredible. The Mansion also has a self-contained kitchen that provides food for more than a thousand guests; the Mansion chef does all of the catering at the parties. A great pad, fresh food, unlimited drinks, a gracious host, and beautiful guests—that was the standard.
There are five annual parties at the Mansion, starting off with the New Year’s Eve bash, then the Mardi Gras party in February, followed by Hef’s birthday party in April, then the famous Midsummer Night’s Dream party in August, and finally, the most elaborate of them all, the Halloween party. Hef is a very generous and welcoming host. I think his first and foremost reason for hosting these parties is, as with everything else in his life, to promote the Playboy brand and to continue to live life according to the Playboy philosophy. The secondary reason is that Hef liked to invite hot young girls not only to enjoy as eye candy and hook up his aging friends but also to enjoy their gracious flirtations and to possibly recruit new members.
Celebrities are a staple at Hef’s parties. Without the celebrities, the parties start to look like a gathering of Hef’s cronies trying to pick up girls who are way too young for them. The truth is, the girls come to meet the celebrities. The celebrities come because it’s a fun party where you know you are the center of attention and can have your pick of beautiful, accessible women. The other guys come because they know there will be only a few celebs, so most girls will have to settle for less. Some of the girls come for other girls. Many of the girls come to be noticed by Hef and become a Girlfriend or a Playmate. And everyone comes for the experience itself: to see and be seen, to say you were there, and to have fun.
We, the Girlfriends, liked having the parties because we felt like it was
our
party. I loved the convenience of being able to go up to my room anytime there was a wardrobe malfunction or to fix my makeup. As soon as one party ended, we would begin thinking about what we would wear to the next one. There was extra pressure for Hef’s girls to wear spectacular, one-of-a-kind outfits, so we had to plan early. But we had fun with it; when sky is the limit, you can really allow yourself to be creative. As the Girlfriends, we felt obligated to have the best outfits. It is hard to keep things exciting and original, but we always had to set the standard. Usually we would begin by choosing a color or a theme:
Moulin Rouge
, Pussycat Dolls, or the like. From there, we would go about putting together the outfit. I always started with shoes.... What shoes do I want to wear all night as I walk over the pool area stones? Boots were usually the most comfortable, so I tried to build an outfit around boots. That usually meant something bad-girlish and sexy versus cute and sweet or angelic. It was so much fun. The only limitations to what we could be were our own imaginations. There is a certain freedom about dressing a part and acting out your fantasy.
In the beginning we used to go out the night before the party, since Friday was our club night and the parties were always on Saturdays. Eventually we convinced Hef that going out the night before the party drained us of energy, and it became a tradition to stay in. The day of the party, we would take all day to get ready. It was a ritual: sleep in late, relax, have your hair and make-up done, get dressed. It was always exciting to see what the other girls were wearing. We would all meet in Hef’s room and make our big entrance downstairs. One after another we walked down the curved staircase, hoping not to trip and fall as the flashing light of the cameras and all the guests’ eyes were focused on us. We would then pose in the great hall for the official group party shot. Our arrival meant that the party had officially begun. We then made a second grand entrance, into the party tent, followed by a ceremonious walk to our table. We then sat in our hierarchical order, and that was supposed to be our basic station for the night.
But where there is a will there is a way, and when the boys show up, the girls will play. At the beginning of a party we sat there dutifully smiling and posing for pictures, all the while keenly aware of which guests were arriving at the party. We sat there as the ever-gracious hostesses and made goo-goo eyes with hot male celebrities. And as soon as the party was rowdy enough for Hef to be distracted, we would excuse ourselves to go to the bathroom, taking the longest possible route to get there. Our next excuse was to go get food, and after flirting and chatting with the guests, we always made sure to grab a plate of food on our way back to the table and announce to Hef how happening the party was and how we had to wait in line. After that, when everyone had a few drinks in them, we would basically sneak away as soon as Hef turned his head. He would always leave the party early. This was good and bad—bad because we wanted to stay longer, and good because we figured the sooner he went to bed, the sooner we could sneak back down and hang out freely by ourselves.
Let’s take a closer look at the five annual Playboy Mansion parties.
New Year’s Eve Party
The party calendar began with the New Year’s Eve party, my least favorite of the year. The reason is not because of the décor or the food or a lack of festive spirit, but because the odd mix of guests lacks the usual energy associated with Mansion parties.
It is simply that most people like to spend New Year’s Eve with their significant others, and since Hef is so strict about not inviting men, many girls do not want to show up solo. According to Hef, “a good party has more good-looking women than men,” but most women want to spend New Year’s Eve with a date. Also, it is a time when people are usually with close friends and family, and Hef does not usually permit his guests, other than the Girlfriends and his close friends, to bring more than one friend to the party. As a result, a lot of celebrities and hot, fun people do not attend the New Year’s Eve party. It is a random mix of Hef’s older friends, a handful of celebrities, and mostly female singles. The Mansion is a good place to go on New Year’s Eve only if you are single and at least a couple of your friends are also invited to the party.
The New Year’s Eve party is more elegant and subdued than all of the others. The décor is usually black, white, and sparkly: white flower centerpieces, silver chairs, black sparkly tablecloths, a black-and-white checkered dance floor. There is also a greater contrast in what the guests wear; a lot more women in dresses and men in suits, unlike at the other parties, which are all lingerie. As time went on, even the Girlfriends started to wear more clothes for that party. The last year I lived at the Mansion, Emma, Susan and I all wore short black dresses, Holly wore a silver sparkly flapper dress, and Bridget wore some bizarre gold get-up.
The New Year’s Eve party was not only mellower in terms of décor but also in terms of the shenanigans that went on. Nothing much happened, despite our efforts to create fun. One year, Emma invited some guy she knew from the East Coast and his brother. She got them on the list because they were musicians. She kept sneaking off to the game house to smooch with this guy, and I would go with her to make sure she didn’t get caught. I think she did it out of boredom, and her idea was that I would hook up with the brother, but it wasn’t my thing. I wasn’t bored enough to hook up with random people, despite my occasional Grotto fantasies. There was also a big movie star at the party who hooked up with Susan’s friend, whom Susan invited to the party as her guest. I was shocked to see it happen because I had just watched a TV special about him, how he met his wife, and I remember thinking what a great relationship they had.
Typical Hollywood illusion
, I thought.
The last New Year’s Eve party I attended as Hef’s Girlfriend was in 2004, the year I moved out of the Mansion. After doing Vegas and taking Manhattan, we capped off a trio of
Playboy
fiftieth anniversary bashes with a blowout New Year’s Eve spectacular at the Mansion. Minutes before the New Year arrived, we gathered on the dance floor, where we were swarmed by dozens of women hoping to kiss Hef, pushing and shoving, as balloons fell from the ceiling and engulfed the party. It was a fun way to bring in 2004 and a fitting way to celebrate the golden anniversary of the magazine.
The only time I really enjoyed the New Year’s Eve party was when my parents were visiting me for Christmas and they came to the party for a couple of hours. It was nice to share the experience with my parents, who had never been to a Mansion party; after all, this was the classiest party as far as the dress code and behavior went. My mom was excited to meet some actors from the soap opera she watches. My father was just mesmerized. Unfortunately there were not too many celebs other than ESPN’s Dan Patrick and Blink-182 drummer Travis Barker, who rang in the New Year in style alongside dozens of sexy Playmates. Because of my mom’s back condition, they weren’t able to stay too long, so I called Justin to pick them up at the back gate of the Mansion. I walked my parents out, and they got into his car. It was so hard to see him there on New Year’s Eve and not be able to walk him into the party. He wasn’t doing anything that night. He took my parents back to my apartment and hung out with them. It was things like that that made me appreciate him and really consider a future together when I left the Mansion.
Mardi Gras Party
A month and a half into the new year, we celebrated Mardi Gras. When I was first invited to the Mansion, this party was the Valentine’s Day party, but that concept wasn’t very successful. Playboy parties are mostly girls, and on Valentine’s Day, you are either with your partner or you are looking for one. On Valentine’s Day, Hef took us out for dinner and—as I said before—gave us a small gift, usually Playboy paraphernalia such as panties and tops. No diamonds or pearls like everyone imagined we got from our wealthy and famous boyfriend. Anyway, the party was then renamed the Mardi Gras party—a fun, provocative theme.
The Mansion was decorated in bright colors, and hundreds of beads were handed out. It seemed that more guys were invited and the party was a success. Some of the guests included Justin Timberlake, George and Geoff Stultz, AJ McClean, Matt Cedano, Seth Green, Wilmer Valderrama, and more. The sexual dynamic was increased—the men used the beads to get women to take off the very little clothing they had on to begin with. It was a fun, carefree party. The wild theme of the party allowed the guests to get even more creative with their outfits; many went topless, and outrageous feather and fur hats were seen everywhere. The Girlfriends wore whatever we could come up with. I remember one year Emma and I got matching little outfits: a frilly bra top and see-through pants (her lace was red; mine was pink). We were in Emma’s room and we were just about to go downstairs to the party when a girl that was hanging out with us arrived: she was wearing the same outfit as Emma. Normally, if another girl is wearing the same thing it is not more than mildly annoying. But this time was different because this girl was sleeping with Hef and hanging out with Hef and was therefore invited to sit at our table. We could not have two girls at the table wearing the same thing unless it was preplanned. I could see Emma was upset and didn’t know what to do. So I had to step up. I told the girl that she had to change her outfit. Emma and I were Hef’s Girlfriends, and we had planned for days to wear matching outfits, and I said I was sorry, but if she wanted to sit at our table, she would have to change. I then told Emma to show the girl some alternative outfits. Eventually she ended up putting on some psychedelic one-piece suit. She later complained that I bullied her. But I had to protect my friend’s interests, and I would have done that for any girl in the group. Despite our differences and internal problems, we were bonded. This girl was just a passerthrough, some girl Hef slept with occasionally but was not interested in and would never be a Girlfriend.