Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny

by Holly Madison

  In the episode, Bridget revealed through a stream of tears that she had auditioned to be a centerfold years earlier but didn’t make the cut. Hef had basically told her it was never going to happen.

  “I’ll believe it when I see it,” Bridget said through a forced smile during her one-on-one interview. It was a small window into what was really going on inside Bridget’s and my heads.

  Earlier in that same episode, you heard me rattle off the same canned answer I’d given for years about whether I wanted to be in Playboy.

  “People assume that I came here wanting to be a Playmate and that that’s my goal,” I said. “The choice is extremely clear to me. I would much rather be Hef’s girlfriend. Hef and I are so much in love. That’s not even a comparison to me.”

  But just because I valued being Hef’s girlfriend didn’t mean I still wasn’t dying for a pictorial! In fact, the two things had become intertwined in my mind. Since the ’50s, all of Hef’s main girlfriends had appeared inside or on the cover of Playboy—except for me. And by this point, it was humiliating. People would always ask me why I wasn’t featured in the magazine and I felt the need to make excuses for it by convincing people that somehow I was special because I wasn’t. Hef was keeping me for himself, I would explain. What else was I supposed to say? My boyfriend thinks I’m ugly?

  My shock and joy was genuine when Hef revealed that we would be shooting for the magazine. None of us expected it, so the reactions the cameras caught were absolutely sincere.

  I’ll give the man this: he knew what made for good TV.

  He also knew the importance of good timing. By allowing us to appear in the magazine, Hef would be cashing in the biggest insurance policy he had to keep us safely behind the mansion bars. But Hef knew something we hadn’t yet figured out: the show was positioned to be a runaway hit for the network, so he no longer needed the magazine as a guarantee. He had better bait: fame.

  The debut season’s arc revolved around our feature and possible cover. It wasn’t until about halfway through season one that shooting began for the pictorial.

  Hef allowed us to choose between the two staff photographers for our pictorial: Arny Freytag and Stephen Wayda. For years, I had seen countless Playboy photo shoots come through Mary’s office and I had absorbed every detail from conception to execution, from the first click of the camera to the ink on paper. I was so excited to finally be a part of that process myself. You would think that dating the magazine’s editor in chief would have afforded me a sort of security and confidence before shooting the pictorial, but it was the total opposite. We couldn’t have been any more anxious about the ordeal. We were way more nervous than just some random girl plucked from obscurity and thrown into a shoot. We had firsthand knowledge of just how fickle and critical Hef could be and we were petrified that we would somehow screw it up and he would just scrap the entire pictorial. After talking to a handful of Playmates, I decided we should go with Arny. While Stephen is an extremely talented photographer, he worked best with more experienced models who knew how to move in front of the camera. Arny worked best with rookie models; those straight-off-the-farm girls who needed help posing every inch of their body. When you haven’t done much of it, modeling can be quite a clumsy sport. Kendra, Bridget, and I needed help squeezing our three bodies into an 8.5" × 11" frame—while looking as amazing as possible.

  The day of our first shoot I was absolutely ecstatic. We were told to arrive to the mansion’s bathhouse in the morning for hair and makeup wearing nothing but a robe and slippers (tight clothes and shoes would leave lines on the body—and we couldn’t have that!). I couldn’t believe I was finally getting the full Playboy beauty treatment. For years I had watched girls transform into these glamorous creatures with the help of the expert editorial beauty team. Even with my weekly allowance, I would have never been able to afford the beauty team Playboy magazine used. In the early days of Hef’s seven girlfriends, it was standard practice for the girls to call in the Playboy glam squad before evenings out and large parties. By the time I arrived on the scene, these were the kinds of lavish expenses that Hef had cut back on. Sure, we would occasionally head to the salon before a red carpet event, but we had never yet experienced the crème de la crème. The Playboy glam squad was legendary. It comprised some of the best artists in the industry—and they didn’t come cheap.

  The ultra-talented Kimberly Ex did my hair and makeup: full, barrel-curled platinum locks with a bronzed face, defined cheekbones, thick black eyeliner, and carefully drawn lips. From the neck down, we were expected to be in top physical shape. The only help we were given in that area was some baby oil mixed with bronzing lotion to give our skin a smooth sheen. I was over the moon with my reflection. I mean, I actually looked like the girls on the pages of Playboy! First, we shot a series of clothed setup shots, which included a shot of the three of us hula hooping on the great lawn in bathing suits. It was mostly intended to warm us up before diving into the deep end (naked), but they ended up coming out great and one of the shots was published. The next setup had us in sexy cocktail attire standing in front of Hef’s limo in the mansion’s main driveway. After a few minutes of shooting, Hef appeared on set to join us for a few snaps.

  How cute, I thought, he wants some behind-the-scenes shots of our shoot for his scrapbook.

  Finally, it was time to begin shooting our nudes. By that point we’d each become considerably more relaxed in front of the camera. As Arny positioned each of us along the rocks in the mansion’s infamous grotto, we were all laughing and goofing around. It was easily the best time the three of us had had together in what felt like months. When Hef came out to check on the photos, he was so happy with the results that he added a last-minute setup for the three of us in the bathhouse shower. It was already pretty late in the day—the shoot had gone longer than intended—but I couldn’t get enough. The crew began setting up a final shot, but Bridget was scheduled for school. She had a final exam for one of her classes that she couldn’t get out of. Apparently her professor didn’t qualify shooting a Playboy pictorial as an acceptable reason to miss class. After a few minutes debating whether or not she should just skip (which would have resulted in a failing grade), Bridget dashed off to campus for her test.

  Truthfully, it didn’t feel odd shooting without her. I knew they wanted a lot of content to choose from and we still had the rest of the week to finish our pictorial. As far as any of us knew a “Bridget/Kendra” or a “Holly/Bridget” setup could have been on the books for the following day. Plus, shooting with just two girls was much easier than trying to arrange three. With wet hair and perfect makeup, Kendra and I playfully lathered each other up with sponges and bubbles in the tropical rock shower. Because it was one of the easiest sequences, it resulted in some of the sexiest shots of the entire pictorial.

  The following day was hands down my favorite. The photographer and crew buzzed around the mansion’s second floor preparing for our individual photos. Set in each of our bedrooms, the shoots were designed to showcase our unique personalities, which was refreshing. To reflect Bridget’s sweet and playful demeanor, her pictorial featured her swathed in a delicate see-through negligée surrounded by plush pillows in her pink-on-pink-striped room. Kendra looked absolutely amazing in a scrap piece of football jersey with knee-high athletic socks and straddling a bunny head chair in her messy room (which was tidied up substantially). My shoot was in Hef’s bedroom and was intended to be reminiscent of old Hollywood. The beauty team styled me like a ’40s movie star (minus the red lipstick) and the photographer draped me over an elegant wood staircase wearing nothing but a pair of vintage peach marabou bedroom mules. It was the most beautiful I had ever felt. Like giddy schoolgirls, we snuck into each other’s rooms to get a peek of one another’s shoot. Each setup was unique and tailored to our personalities, so there was no competition and we were genuinely excited for each other.

  Stepping into the Playboy Studio in Santa Monica for our final shoot was surreal. It wa
s the very same studio I had nervously visited with my old friend Heather years earlier. We had decided to try a Playboy Polaroid audition, praying that we would be selected. My life had come full circle, in a way. While the journey wasn’t quite how I imagined it, I was arriving at the studio to shoot a cover for the magazine.

  Surveying the massive studio space, I immediately noticed that the crew had constructed an exact replica of Hef’s bedroom for our set.

  “Why didn’t we just shoot at the mansion?” I asked one of the crew members, totally bewildered. He couldn’t produce an answer. No one could. I suppose Hef was more inclined to waste thousands of magazine dollars rebuilding his bedroom rather than being inconvenienced for a few hours.

  Playboy photo editor Marilyn Grabowski used a page from a foreign issue of Playboy as inspiration for our first setup: three identical brunettes piled on top of each other in bed. Throughout the sequence, we couldn’t keep a straight face. Since none of us were ever remotely attracted to one another, it never even crossed our minds to “act sexy.” Posing for such a risqué shot felt incredibly awkward, but it turned out that the laughter worked in our favor because the photos ended up looking quite erotic.

  Finally it was time to shoot our cover. Marilyn positioned each of us on a slightly slanted bed covered in silk sheets (that she constantly kept smoothing, draping, and switching), while Arny positioned himself on scaffolding directly above us. Because we were nude and flat on our backs, our breasts had to be taped up to produce the amount of cleavage needed for the cover. Contrary to the quick sequence audiences saw, the cover shoot lasted several days. Our hyper-meticulous, Devil Wears Prada–esque photo editor kept analyzing every excruciating detail down to the placement of a single curl. She must have changed the silk sheets from black to white to black again a hundred times—sending the photographer into a tailspin. Despite all of it, I was having the time of my life. The white, skylight-lit studio pulsated with creativity energy and positivity. It was such a welcome change from the musty atmosphere of the mansion.

  “I wish I could come here every day,” I whispered to Bridget as we lay on the slanted bed.

  “I know, me too,” she said.

  During our lunch break, Stephanie Morris—a junior photo editor at that time—called us down to her office to fill out “paperwork.”

  Hef hadn’t spoken to us about how much we were to be paid for our pictorial, but we were about to find out. Rates for amateur models start at about $25,000 per pictorial. In 2005, reality-star types were earning roughly $40,000 to $50,000 for a pictorial. Hef’s former girlfriends the Bentley twins each received $100,000 for their cover and pictorial years earlier. When it came to actual celebrities (like Denise Richards, Drew Barrymore, or Cindy Crawford, for example), paydays could be near a million dollars.

  Truthfully, Hef had been so stingy with opportunities for the girlfriends to appear in the magazine that I wasn’t expecting much. At that point, I was just grateful for the chance. For years the mansion was hell because girls were fighting over this very opportunity—and here I was. Not them.

  When we got to her office, I quickly scanned over the release she pushed under my nose. I didn’t think much of it until I noticed the $25,000 fee we were each being paid for our pictorial. Since this was technically considered a “celebrity pictorial,” part of me thought we deserved more than the stock fee. Even something like $30,000? Don’t get me wrong, it wasn’t the dollar figure that upset me, it was that we were viewed as no greater a commodity than any other girl who had walked these halls. We were simply a dime a dozen.

  Still, $25,000 was the most money I’d ever had! I immediately started planning what I would do with it. I knew I wanted to put some in savings for the investment property I dreamed of buying—and maybe I could use a bit to buy that Louis Vuitton travel case that I’d been lusting over for years. It seemed like a fun way to commemorate this major goal I had just achieved.

  This is exactly what I need to get back on my feet, I thought.

  Bridget had tested to be a Playmate years earlier, so she knew what Playmates were paid and that with the growing popularity of the show, we deserved much more than what Playboy was offering. But she also knew there was zero point in arguing about it. She slowly put her pen to paper and signed away the photo rights. But worse than our bottom end of the scale pay for the pictorial was the fact that despite being the stars of the show, Hef and the producers decided that Bridget, Kendra, and I wouldn’t receive a single dime for the first order of The Girls Next Door. Hef would later argue that he considered our pictorial fee our payment for season one. He clearly knew the value of a “buy one, get one free” deal. I recall someone connected to the show reminding us that we got “free room and board” at the mansion. This guy clearly didn’t realize the heavy price of this “room and board”: how restricted our freedoms were and all that was expected of us.

  While the filming on the first batch of GND episodes was wrapping, Kendra had finally gathered the courage to bring the issue up during a meeting the three of us had with the show’s highest-ranking producers.

  “Shouldn’t we like . . . be getting, like . . . paid for doing the show?” she asked nervously. It really was a valid question and she broached the topic in a delicate way. We were working countless hours, opening up our private lives, and baring our bodies for public consumption, so in her mind that was worth something. She wasn’t being accusatory; she was just being logical.

  The response she received was not what any of us were expecting to hear.

  One of the producers took a deep breath and suddenly became very firm before spitting out slowly and methodically (so that our tiny little brains had time to absorb this fact): “You. Are. Replaceable.” (That would become the unofficial motto of GND for seasons to come.) “This is not a show about the girls who live at the Playboy Mansion. It’s about Hugh Hefner and who he chooses to date. It is not about any of you.” We were constantly reminded that the show was Hef’s show—our contributions were irrelevant. We were the decorative icing, not the cake. According to our boyfriend, he could have splashed any three blondes on screen and found instant success. This producer’s firm response quickly silenced Kendra into submission.

  In the days and weeks following the photo shoot, I routinely stalked Mary O’Connor’s office looking for the Playboy “brown book” (a mock-up of an upcoming issue for Hef’s approval made from thick, brown, grocery-bag-like paper). I’m a self-proclaimed super snoop, so I spent hours lingering around her desk hoping to get a peek of our pictorial. Eventually, my persistence paid off.

  As it appeared on the show, we were all oh so naturally sitting in a circle on the floor of Bridget’s room when Hef came in to present the book to us. In actuality, Bridget and I spotted the book in Mary’s office one afternoon and quickly flipped through it to get a first look at our feature. When we finally saw it, we weren’t as thrilled as we could have been. Physically, we looked great. The photography, lighting, and makeup that Playboy used at the time was so flattering, very little retouching (if any) was needed. Even back then, most people assumed that the women of Playboy were mainly a product of Photoshop, but that wasn’t the case with most of the pictorials. Kendra would eventually request to have her labia Photoshopped out of one of the pictures where her legs were in the air, but that was about it. Years later, Playboy would auction off that brown book, complete with Kendra’s crotch circled in Hef’s red pen. So much for not having that out there! But it wasn’t what we looked like that bothered us, it was which photos were selected.

  The large opening shot just so happened to be the picture of Bridget, Kendra, and me in our sexy cocktail attire with Hef plastered right between us. Remember those brief few clicks he casually wandered into? Maybe it’s just me, but I’m not so sure men picking up the magazine would be all that turned on by a septuagenarian man front and center. We quickly realized that none of our individual looks had been chosen—the one piece of the pictorial that could differentiat
e us from one another. The steamiest photo in the feature was a full-page photo of Kendra and me in the bathhouse shower. Like I said, at the time we didn’t think anything of the extra shots, but looking at it in context was quite different. This was one of the largest photos in the pictorial, and it was very clearly missing one-third of our group. Needless to say, Bridget was upset. I’m certain Kendra or I would have felt slighted as well, but Bridget had dreamed of becoming a Playmate even longer than Kendra or I had, so she took this quite personally.

  On the show, Bridget returned from class already worked up over the shower ordeal. On camera, she confided to her sister about how upset it made her to be excluded from the day’s final setup and decided to speak with Hef about it. In the scene, viewers see Hef come to comfort Bridget, who was sitting on the floor playing with her cat.

  This is the exchange audiences hear:

  BRIDGET: I know, but that’s what I’m saying; everyone would feel the same way.

  HEF: Okay, okay. Absolutely. Let me see what I can do. That isn’t exactly the toughest one to do; it’s a shower and hair.

  BRIDGET: I know, but I just feel like saying something makes me seem ungrateful, and I’m not.

  HEF: Listen, I know how important all of this is to you. I’ll figure out some kind of solution, honey.

  In real reality, events didn’t play out that way. Bridget didn’t discuss the shower sequence with Hef until after we saw the brown book—and long after the pictorial shoot had wrapped (which was why Kendra appeared so agitated at having to shoot again). At the end of the episode that aired, people can clearly see the two-shot of Kendra and me in the brown book when Hef is showing it to us (the photo that went to press was the shot of the three of us in the shower).

  Bridget was sensitive about how her reaction would be perceived, so she told producers she wished to speak to Hef off camera and asked that they respect her privacy. The crew preferred to film everything as it was happening, but they eventually agreed that Bridget could speak to Hef off camera. Reality producers love to find loopholes, though.