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

by Holly Madison

  For the most part, we chose our battles and did as Hef requested when it came to our careers, but the slot machine idea struck a chord. “No way,” an acquaintance of mine told me over the phone one afternoon. “I’m going to look into this. Slot machines are big money, Holly. They’re planning on using your names and likenesses. They have to pay you for that.”

  Shortly after the licensing department was approached about compensating us, the slot machine plans came to a grinding halt. It seemed insane to abandon it altogether, but it was never brought up again. Either there were too many hands in the pot to make it profitable or no one wanted to concede that we should be paid for the use of our names and likenesses. God forbid they open up a can of worms by making us feel important or put enough money in our pockets to feel independent!

  My last attempt at foraying into the world of Playboy licensing was a pitch for Bridget, Kendra, and me to create swimwear lines—an idea they were initially enthusiastic about. They immediately green-lit the project and I began designing my collection. It went far enough into development that samples of all of my designs were manufactured. But one day, without any explanation, the project was shut down. Bridget, Kendra, and I were so used to defeat by this point, we didn’t even question the decision. It was never mentioned again until one day I noticed the Playboy catalog on Mary’s desk. I spun it around to face me and gasped.

  There she was: a sultry Sara Underwood lying across the cover in a sleek, sophisticated black monokini with a tiny gold Playboy logo beneath the belly button.

  “What the fuck?” I whispered under my breath. That was my design! Did Playboy licensing actually go ahead and manufacture and sell my design without even letting me know? Sure, it could have been a mistake, since the same manufacturers that made the Playboy line made the GND samples, and maybe Playboy even had the legal right to use my ideas this way, but it still made me feel like dirt. It wasn’t about the lack of compensation. It was about feeling owned, like I was Playboy’s personal property and could be walked all over like a doormat. I didn’t even bother confronting anyone about it, because I knew it would be a losing battle. It definitely made me question my loyalty to the brand, though.

  As GND went into its fourth season, I finally had the opportunity to take Bridget and Kendra to my hometown. We visited Bridget’s and Kendra’s respective hometowns in the first two seasons and I had been lobbying to take the girls to Alaska for quite some time. Needless to say, it was a little more expensive to get to Alaska than to Lodi or San Diego, so it took a little time for production to come around. Hef even tried to throw a wrench in the plans when he made it clear that of all the places he had never wanted to go, Alaska topped the list.

  We were finally able to make the trip, along with my mom and dad (Hef stayed home, of course). I loved taking the girls to Craig, the tiny town I grew up in, and to Ketchikan, the nearest city, where my family and I used to go when we needed to buy something that Craig couldn’t offer (there were only a handful of stores in Craig). Bouncing back and forth between islands on the tiny Otter plane was an adventure in itself. Our plane broke down midair and the pilot had to make an emergency landing. This was one time Kendra was really afraid of flying. She had to have a few drinks before getting on our return flight.

  Alaska is rugged and not for everyone, so I appreciated that the girls were enthusiastic about the trip and made the effort to have a good time. The episode turned out to be my favorite of the entire series. One shot in particular stands out in my mind. The three of us took a moment to quietly swing on a swing set while the camera shot us from the ground, three dandelions of varying height echoing our three figures in the foreground. It seemed like such an innocent moment, and the whole episode captured us as ordinary, real people, not as the “Mansion Mistress” cartoon characters we usually played on TV.

  Later that season, the cameras returned to Studio West with me for an episode titled “Go West Young Girl.” In the process of finding a Playmate for the upcoming September issue, I invited four candidates out to test for the slot. There was a brunette named Melanie from San Diego, raven-haired Valerie Mason from Louisiana, platinum blond Kayla Collins from Pennsylvania, and a quirky 18-year-old from Las Vegas named Angel Porrino.

  Not only was I thrilled to have an episode focus so much on the job I had grown to love, I made new friends and even found a few Playmates in the process. Valerie Mason, with her classically cute face, would end up being chosen as Miss September. Kayla, surprisingly, was turned down by Hef for “looking too much like too many other Playmates.” Hey, at least he was starting to appreciate variety! Kayla ended up becoming Miss August 2008 after Hef’s friends made a fuss over her when he screened the GND episode for them.

  My favorite candidate was Angel Porrino. She had an electric personality and the most fun sense of humor. People couldn’t stop laughing when they hung out with her, especially me. I’d never had a friend I’d laughed so hard with. Along with German Playmate Giuliana Marino, we became an inseparable trio, hanging out and goofing off whenever I had free time. Hef didn’t end up selecting Angel as a Playmate and I was very sad to see her go when it was time for her to return home.

  My sister’s wedding made up two episodes of season four: “Jamaican Me Crazy” and “Wedding Belles.” I was surprised when my sister said yes to the idea of The Girls Next Door covering her wedding, but since she had planned a very small destination wedding in Jamaica, it turned out that she thought it would be a great way to share the celebration with all of her friends that couldn’t be there.

  Bridget, Kendra, and I couldn’t have had a better time. For whatever reason, Hef wasn’t interested in attending, but I can’t imagine his cranky, high-maintenance personality in laid-back Jamaica anyway. The three of us girls had an amazing few days at Sandals Negril, relaxing, zip-lining, and exploring with my family. There was no drama, just a truly memorable trip and a beautiful beach wedding. I was the maid of honor, my sister looked stunning, and my family and two closest girlfriends were as happy as could be. Who could ask for anything more?

  Playboy could. Just before filming was set to begin on season five, there was a mad rush to get Bridget, Kendra, and me under contract. Prior to the first episode of the series, we had each signed the most basic of television releases—and nothing more.

  Realizing that the stars of this hit show were theoretically free to walk away and pursue other television opportunities at any time, someone must have panicked. Unbeknownst to us, Hef arranged to have us contracted under Alta Loma (Playboy’s production company), which basically meant that we would have a talent agreement binding us to Hugh Hefner. Letting us negotiate directly with the network was never going to be an option, probably because it meant he would have had to relinquish too much control over his girlfriends. After all, what if E! offered us something greater than being one of Hugh Hefner’s blond bimbos? As I understood it, the network was willing to work with us in this fashion as long as Alta Loma could show they had us under contract, and fast.

  It all happened so quickly, I can’t even remember how I initially heard about the contract. What I do recall is getting really worked up and marching down to the master bedroom to tell Hef I had no intention of signing.

  “I think it’s in bad taste to sign a contract to be your girlfriend,” I maintained. Given that the show was about “Hef and who he is dating,” as opposed to any of the three of us (as they liked to remind us regularly), I felt signing a contract with him was taking away my option of walking away from the relationship at any time. It would be just another facet of this relationship that would make me feel like a hooker. “It’s just weird.”

  “I understand the notion, but it’s important to me that you sign it,” he said, looking at me with sad puppy dog eyes. “If you care about me, you’ll do it.”

  In the end, it was always about Hef. Quietly, I did my best to consider my options. I didn’t want to be coerced into doing anything else for this man.

  Sensin
g my hesitation, and realizing that my heartstrings might not convince me, Hef decided to appeal to my business sense, telling me that if we didn’t all sign, the network might not order another season.

  As further encouragement, Hef had told me Bridget already signed her contract, but I didn’t learn until afterwards that she did so completely against her better judgment. As a reasonable person would, Bridget asked to have some time to have her lawyers look over the paperwork but was denied. I imagine she was given the trademark mansion attitude: “If you don’t like it, you can leave.” Begrudgingly, she signed the contract.

  “Okay,” I finally relented. “I’ll look at it, but I want you to know, I don’t like this.”

  “I understand,” Hef said, unable to contain his smile. He didn’t care what the hell I thought, as long as I walked my butt down to the office and signed those papers.

  Still in my pajamas, I trudged down to Mary’s office at the other end of the mansion. Without saying a word, I sat myself in the chair next to her desk and started playing with her white Maltese pup named Miss Kitty.

  “So,” Mary started, looking over the top of her small-framed eyeglasses. “Did Hef tell you about the contracts?”

  “Yes,” I grumbled, before pleading my case. “And I’m not thrilled about it. I think it’s wrong.”

  Mary sat in silence with her arms folded, allowing me my few moments to vent.

  “Because the show is about Hef’s girlfriends, I feel like I’m signing a contract to be in a relationship,” I whined. I was beyond frustrated. I had my back against the ropes. If I wanted to move forward with the show for a fifth season, I had to bind myself to Hef’s production company. What if I wanted to move out? Or do another show? I felt like this contract might make that impossible.

  “That’s not really what it’s about, Holly,” Mary reassured me, her voice smooth and calm. “E! is just hesitant to move forward with the show if their talent isn’t under any kind of contract. That’s all.”

  “I know, but . . .” I allowed my voice to trail off. I’d already had the same argument with Hef and it wasn’t going to result in any different outcome with Mary. I fell silent for a few moments before asking, “Do they have to be signed today?”

  “Yes,” Mary said very matter-of-factly. “They need them back today.”

  “Why did we get them so last minute, then?” I asked, my anxiety starting to escalate again. “We don’t even have time to look them over!”

  “The contracts are with Alta Loma, dear,” Mary went on, sidestepping any explanation as to why we were just now receiving them. “You know if there’s a problem, Hef will release you from it.”

  But would he? I know that in Mary’s heart, she sincerely thought that Hef was a good man—just as I believed at the time. But a nagging voice in the back of my head kept warning me not to trust this situation.

  If signing this contract was really so important to everyone, I decided to just get it over with. I knew that ultimately I had no choice. Hef would find a way to corner me into signing it, so I might as well just save myself any further aggravation.

  “Fine, “I said, grabbing a pen on Mary’s desk. “Where do I sign?”

  I scribbled my name on the contract that Mary nonchalantly shoved under my nose and handed it back to her.

  “Now . . . what to do about the Kendra problem,” Mary continued.

  Kendra was in the Dominican Republic for a paid nightclub appearance, so she could hardly sign the paperwork by E!’s alleged deadline. But Hef and his team must have found some kind of solution, if all three of our signed contracts were indeed delivered to E! that afternoon.

  I can’t say this with certainty since I never witnessed pen to paper, but the gossip around the mansion was that someone on Hef’s staff must have had to forge Kendra’s contract in order to meet the network’s deadline. Of course it’s also possible that E! never even gave Hef a deadline or that he used a false date to get us to sign without giving us the opportunity to really review the documents. Who knows? All I know is, the whole thing seemed highly unusual to me.

  OUR FIFTH CYCLE WOULD end up being a season of growing pains. Looking back, I see that it makes sense that this was our last season as a trio. From an outsider’s perspective, however, everything looked like it couldn’t be going any better. The series had become such a phenomenon, there was even a movie being made about it. Well, sort of. The House Bunny, starring Anna Faris, was a comedy set at the Playboy Mansion, centering on a fictional Playmate who finds herself kicked out of the mansion (upon turning 27) and takes refuge in a sorority house. In the film, Anna plays a mansion resident named Shelley, a character clearly based on Bridget.

  “You should have been the sporty one,” Kendra teasingly pouted at Anna the first time we met her as she prepared to shoot a scene in the mansion’s backyard. Anna was done up with curly blond hair, a frilly pink outfit, and her character had a grumpy pet cat, similar to Bridget’s cat, Gizmo. Bridget’s pink-striped bedroom was used as Shelley’s room in the movie. Even the high-pitched voice and sunny, Pollyanna attitude Anna affected for her character were very much Bridget’s style.

  We had cameos in the film, playing ourselves for a few scenes. The movie would hit the number two spot at the box office on its opening weekend. Even I couldn’t believe what a phenomenon this frilly, frothy, girly (and in many ways make-believe) version of the Playboy world had become.

  Not everything in our world was cotton candy and fluffy bunny tails, however. That year, Kendra started taking Accutane for an acne problem she had grown increasingly self-conscious of. To me, Kendra was a beautiful girl, with acne or without, so on one hand I couldn’t understand her paranoia, but on the other hand I could. Every girl who ever lived at the mansion knew that her entire value, in Hef’s eyes, depended on the way she looked. In fact, in an interview from the previous year for an Elle magazine article, Kendra confessed: “I’m very insecure right now about my face. I get scared with Hef looking at me at the mansion and maybe thinking I’m ugly.” I certainly understood how she felt. In that same article, Hef went out of his way to tell the writer that I had only “become beautiful” and that I “didn’t look the same” as when he first met me, going on to attribute my new acceptability to my nose job.

  Gee, thanks, Hef!

  Whether it was an excuse not to have to adhere to the filming schedules she hated keeping or if she really had grown debilitatingly insecure, Kendra often refused to come out of her room to film scenes. I would find out later that this was around the time she started secretly seeing her future husband, Hank Baskett, so maybe that factored into the equation as well. The producers were desperate to find someone to take Kendra’s spot, should she decide to stop coming out completely.

  No one was talking about adding a new girlfriend or anything, but I was asked to recruit some girls that I thought would be good for the show to stay at the Bunny House for a month or so while we filmed. I chose Laura Croft, a wild and crazy Playmate from Florida; Kayla Collins, the bouncy blonde from the “Go West Young Girl” episode; and Angel Porrino (also from the “Go West” episode), the funny girl with the high-pitched voice from Las Vegas.

  Having the girls around proved helpful as Kendra refused to participate in quite a few of the episodes (sometimes she would salvage her spot at the last minute by agreeing to film something by herself; other times she was just missing in action).

  When Bridget produced a campy B movie called The Telling, Kendra didn’t take part, even though she was offered a role in the film. While Bridget and I traveled with Laura, Kayla, and Angel to Chicago, Dallas, and New York to scout Playmates, Kendra chose to stay home.

  One evening Hef popped around the corner into my vanity area and announced that he was kicking Kayla out of the Bunny House.

  “Why?” I asked. I couldn’t imagine what Kayla had done to warrant such dislike and was eager to stick up for my new friend.

  “Kendra doesn’t like her,” he said firmly. “She thi
nks Kayla is starting trouble between her and some of the other Playmates. She feels like she is trying to take her place on the show. She’s toxic. She has to go!”

  “Are you sure?” I asked. “I don’t get it, maybe I should ask Kendra about it. Kayla likes Kendra, as far as I know. Who is she supposedly starting problems with?” I asked.

  “Other Playmates,” Hef reiterated, as if that made him any more clear than before. He went on to say how hysterical Kendra was about it.

  I couldn’t figure out what this was really about and pleaded for Hef to let Kayla stick around for the remaining weeks that she was scheduled to stay.

  “I’ll talk to Kendra about it and make sure everything is okay,” I promised, trying to play the peacekeeper.

  Hef agreed to let her stay, but threatened to have her leave if she made another misstep. He waved a finger at me and walked out of the room.

  I wasn’t too worried about the situation; I assumed Kendra felt threatened by another petite, energetic platinum blonde running around in front of the cameras.

  She’ll get over it when Kayla leaves, I thought.

  Later, I would hear through the grapevine that Kendra’s future husband, Hank, was apparently after Kayla before he met Kendra. I have no idea if this is true or not, but it would explain the freak-out.

  For the second half of season five, the girls in the Bunny House left and the three amigos gravitated back together. We invited all of our moms (and our house mother, Mary O’Connor) out for a group spa day, visited Barbi Benton’s outrageous home in Aspen, and went on a road trip for Bridget’s sister Anastasia’s birthday. The three of us attended our friend Stacy Burke’s wedding in Vegas. Stacy was always identified as “Hef’s former girlfriend” when her name popped up on screen during an episode. As if there wasn’t any other way to identify her! Hef truly loved to believe that the highlight of any of his ex’s lives was the time they spent with him. He also loved to remind viewers of all the beautiful women he “dated.”