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

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Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny Page 32

by Holly Madison


  While my cast was handling their newfound places in the spotlight in different ways, I kept busy with work and foolishly pushed my concern about my friends aside. We’ll deal with that when next season’s negotiations come up, I thought. The future seemed so bright that I was sure everything would just repair itself eventually.

  Claire was the front-runner for 2011’s Playmate of the Year and it was suggested that since she and I had become so close, I resurrect my role as Playboy’s photo editor for the pictorial as a special contributor. Despite how desperate I was to get away from Playboy, I actually liked this idea since it put the spotlight on my professional, not personal, involvement with the magazine.

  Given her very era-specific look and curves, I began planning the shoot in my head: a vintage Bettie Page–inspired feature using the plush red Crazy Horse theater as a backdrop. We couldn’t wait to get started!

  As the shoot dates drew nearer, I was excitedly explaining the project to Josh when I got a call from one of the producers. With a heavy sigh, he dropped the bomb on me that we were no longer filming Claire’s pictorial.

  “Why?” I asked, hoping it was just a silly mix-up that could easily be fixed.

  I heard him take a deep breath and exhale. He explained that Hef had just called him and said that Crystal and I had a Twitter fight and that she was really upset about it. He said she threw a fit about it and that Hef had no choice but to take me off the pictorial.

  “Ugh,” I groaned. I had heard through the grapevine that Crystal was still moping around the mansion because she had “her show taken away” and was upset that I was the one still on television. Any suggestion of my presence anywhere near Playboy sent Crystal into a frenzy. What happened to the laid-back Crystal I had seen the last time I visited the mansion?

  “Are you serious? We didn’t get into a fight,” I snapped, exasperated by her immaturity. “Someone on Twitter pointed out that she copied my underwater photo shoot, and later I made a generic post about hating copycats. That’s it. I didn’t even mention her name or reply to the person who pointed it out!

  “I’m sorry that she has a guilty conscience,” I huffed, rolling my eyes. Over the past few years, I definitely began to feel that for whatever reason Crystal was trying to Single White Female me. “And I’m sorry that she can’t deal with people’s comments on the Internet.”

  Crystal had no clue what to do besides follow in my footsteps. Maybe she felt like emulating me was the only safe thing for her to do. In a way, I could empathize with her, since I knew how frightening Hef could be and how scary it could feel to try and step out of the realm of what he expected of you. I had been smacked down pretty hard for cutting my hair and wearing red lipstick and had been afraid to dress any differently than his previous girlfriends, after all. In my “off time” during the day, I had held on to being my own person in some ways, so when Crystal even started copying my private life, I was a little creeped out. She became an overnight Disney fanatic, made a point of tracking down and befriending my old buddy Britney (who had long ago ceased being a mansion regular), and started spending her days with her.

  Crystal acquired the seemingly requisite boob and nose job shortly after moving into the mansion, and after her plastic makeover, Hef handed her a December 2010 centerfold. This was a stark contrast to how the centerfolds had been held far, far away from me and most of the girls I had cohabitated with, but I suppose Hef felt that giving Crystal a centerfold to shoot on GND was safer than giving her a “celebrity pictorial” like he had given me, Bridget, and Kendra. Or perhaps he was finally playing fair for a change and putting her on the same level as the twins; who knows?

  The first photo in her spread looked a lot like the opener from my final self-directed pictorial for February 2009 (standing back to camera naked in between two theater doors). The rest of the pictorial was very old Hollywood, complete with the same style of monogrammed pillows I had requested for a GND calendar shoot two years earlier. Sure, the fact that it was December (my birthday month and favorite time of year) could have been purely coincidental, but I knew how painstakingly produced every last detail of these shoots were . . . including the hat that sat next to Crystal in her centerfold: a fedora adorned with a single sprig of holly. Even her Playmate video had been filmed at my favorite location, the spot I fought so hard to secure for my final pictorial: the Los Angeles Theatre. Knowing how expensive it was to shoot video there, they must have spared no expense to get it done. It was weird.

  Clearly I wasn’t the only one recognizing these “coincidences.” I constantly saw fans on Twitter tagging Crystal and me, saying that Crystal was copying me. Crystal must have seen them, too.

  I was disgusted with both Crystal and Hef. He knew how much I enjoyed producing these pictorials and he took the project away from me as a form of punishment.

  The producer sighed and said he was really looking foward to covering this shoot. I knew he was telling the truth. The crew and I had known each other for years and we all seemed to especially enjoy doing the photo shoot episodes.

  “Me, too,” I conceded.

  He suggested, with a momentary flicker of hope in his voice, that all I would have to do is call and apologize to Hef and Crystal.

  “No way!” I exclaimed. “Why should I have to apologize when I didn’t do anything wrong? That’s idiotic. If he wanted me to direct the pictorial and have it featured on the show, that decision should be separate from any drama Crystal and he are having. Forget it!”

  Knowing Hef as I do, I’m sure part of him got off on the fact that Crystal was jealous and insecure. If I were to engage in this one-sided battle, I’d only give him the satisfaction of feeling fought over. No, thank you.

  I can just see his scrapbook entry now: “Hef cancels Holly’s shoot with Claire due to a fight Crystal and Holly had over Hef.” (He always referred to himself in third person in the scrapbook captions. The whole thing is so bizarre.)

  In your dreams, pal.

  AS SEASON TWO OF Holly’s World wrapped, Lifetime TV was preparing a special on Hef and Crystal’s upcoming June wedding, but it wasn’t to go on as planned. Crystal ended up running out on Hef five days before the 300-guest ceremony was set to take place. The crew was left with nothing to film. I couldn’t begin to imagine how mortified Hef must have felt. Hef’s friends and many Playmates were in an uproar, denouncing Crystal, sometimes publicly on social media. Kendra and I were asked to film a scene with Hef to help fill time in the special, which was now titled Hef’s Runaway Bride. I did it as a favor to production, the same people behind Girls Next Door and Holly’s World, not Hef, though I do have to admit, despite all the negative things I had been through with the guy, I did feel bad for him after such a public humiliation. I wasn’t interested in showing up to say “I told you so” regarding Crystal, I just wanted to try and be a friend.

  I flew into L.A. the day of the shoot and arrived at the mansion early to wait for the production crew in the unusually silent great hall. Suddenly, a bleary-eyed blonde wearing a pair of Hef’s oversize aqua silk pajamas and a noticeable case of bed head appeared at the top of the staircase.

  “Excuse me,” asked Shera Bechard, a recent Playmate who had obviously just wandered out of Hef’s bedroom, “how do I take the dog out?” She pointed down at a King Charles spaniel, the dog Crystal had left behind, who was sitting at her feet.

  “Um, you just open up the door and take him outside,” I said, trying my best not to sound condescending. It was a strange question with an obvious answer, but then again, the mansion was such a bizarre place it would have been easy to assume that there was probably a weird ritual involved with taking one of the mansion’s dogs outside. Thankfully the crew showed up and ushered me down to Mary’s office, saving me from that awkward exchange with Hef’s latest concubine.

  As Kendra and I sat in her mansion office, Mary explained that she had received a call from Crystal when Crystal was at the Jazz Festival. Crystal confided in her that she was real
ly nervous. Mary said she had asked her if the problem was Anna (Anna was one of the two girls Hef was supposedly dating when he was “settling down” with Crystal), and Crystal had said no, that she loved Anna. Mary just shrugged and said she didn’t know what happened between Crystal and Hef.

  By then, we had all heard the gossip that Hef and Crystal couldn’t come to terms on a prenup, leaving them at a stalemate just days before the wedding. So Crystal decided to up and leave—straight into the arms of her secret boyfriend, Jordan McGraw (the son of Dr. Phil . . . what would he have to say about this little love triangle?). One celebrity news site even revealed that she had moved in with him.

  It was the giant elephant in the room, but neither Kendra nor I breathed a word of it. After all, we had a film crew surrounding us and we all implicitly knew that that topic was not something Hef would allow to be included in the special.

  Kendra and I sat down with Hef in the mansion library, a room I had been in a zillion times before, but I had never been this uncomfortable. Despite the years that had passed, there we were—Bridget, Kendra, and me—hanging on the wall. It was a photo from our first pictorial, the three of us piled naked on top of one another. Living at the mansion you start to get desensitized to those sorts of things. Nude photos, no matter how explicit, had all started to look the same to me. But after being away from Playboy for three years, the photo that had once seemed so silly and playful struck me for the first time as incredibly pornographic (which of course was the original intention behind the image in the first place). Who knows, I may have been the one that initially had the thing framed, but by that point I was embarrassed that that photo was still up there for all to see.

  Hef confessed, while looking directly at me, that he proposed to Crystal to avoid making the same mistake he had with me. I remained as stoic as possible, just nodding solemnly like a robot. Giving him—or viewers—false hope was the last thing I wanted to do. We each gave him a hug, offered him our condolences and words of encouragement, and then let him get back to his paperwork.

  The Lifetime special flopped. No one was invested in Crystal and Hef as a couple, and unlike the ferocious media storm, the special failed to mention the other man Crystal was involved with. Though the scandal made a splash in the press, most people who didn’t know Hef brushed it off as a publicity stunt.

  Trust me, Hef may be a publicity whore, but he would never risk his own bulletproof ladies’ man reputation for the sake of a headline.

  Crystal, on the other hand, didn’t have as much reverence for his public image. According to a report in the New York Post’s gossip column Page Six:

  Hugh Hefner’s wedding to Crystal Harris was called off after she secretly planned to ditch the Playboy mogul at the altar in return for a $500,000 media deal, Page Six has exclusively learned. . . . A source told us, “Crystal wanted to ditch Hef at the altar. Her plan was to walk up the aisle and say she couldn’t go through with it. The wedding was to be filmed for a reality special, and her refusal to marry him would be a sensation. She was looking for a tie-in deal of around $500,000 for the exclusive ‘I ditched Hef at the altar’ interview. While there was interest, Crystal didn’t get an offer anywhere near half a million.”

  Crystal continued to milk any ounce of publicity she could get for months: promoting her Playboy cover (the July 2011 cover had been designed to showcase Hef’s newest wife, but at the last minute a sticker reading “Runaway Bride” had to be slapped over the top of it so the magazine wouldn’t look dreadfully out of step and could simultaneously capitalize on the scandal) and Girls Next Door season six’s DVD release (despite barely being in any of the episodes, Bridget, Kendra, and I were on the front of the box along with Crystal and the twins in an attempt to sell more copies). She appeared at a Heidi Montag–hosted pool party, publically pawned her engagement ring, hired an animal lawyer to get back the dog she left at the mansion months earlier, and made a well-publicized visit to Howard Stern.

  In the graphic interview, she told Stern that sex with Hef lasted “like, two seconds. Then I was just over it . . . I’m not turned on by Hef. Sorry.”

  Even from Las Vegas, I’m pretty sure I could see the steam shooting out of Hef’s ears. Nothing gets under his skin more than someone doubting his sexual prowess.

  Unable to keep quiet and in a desperate attempt to salvage his lothario reputation, Hef fired back at Crystal via a series of tweets:

  Crystal did a crazy interview with Howard Stern today that didn’t have much to do with reality. Is she trying to impress a new boyfriend?

  The sex with Crystal the first night was good enough so that I kept her over two more nights . . .

  Sure, her turn on Stern was a low blow, but I was disappointed to see Hef stoop to her level. In the end, they both lost that war.

  When the headlines disappeared, her new relationship ended and people stopped caring about Hugh Hefner’s ex-fiancée, Crystal came back to the mansion with her tail between her legs and the pair wed in a low-key wedding ceremony on December 31, 2013. There certainly must have been a measure of satisfaction for Hef’s ego. The woman who had so publicly embarrassed him ended up crawling back after all—just like he had tried to convince me to do after I met Criss.

  My guest appearance on Hef’s Runaway Bride was the last time I ever saw Hef or spoke to him. I continued to receive letters from him after that, but I just threw them away, because they were always only about him anyway. Three years after breaking off the relationship I could finally say he was out of my life for good.

  DESPITE ANOTHER SEASON OF stellar ratings for Holly’s World (seeing a series high of nearly 2.5 million viewers), the show was canceled.

  E! welcomed a new president at the same time, who decided she no longer wanted the network to be in business with Playboy. “We want to get rid of the trashy Playboy element,” she was quoted as saying. This hurt, since I had been trying so hard for the past few years to separate myself from that brand.

  Kendra’s show was canceled shortly after mine.

  Sure, Playboy got me on television, but it was also because of Playboy that I was taken off television. Many people assume Playboy was my blessing, but most don’t know it was also my curse.

  Truth be told, I was devastated by the cancellation. The cast, production, and I continued to bring in the ratings for the network, but Playboy cast a shadow over my life and I couldn’t escape it.

  I felt terrible that I could no longer provide my castmates with the spots on the show that had brought them so much success. I felt like the Giving Tree after the tree was reduced to a stump and had nothing left to give anyone. I was worried that I would lose all my friends once they learned Holly’s World was to be no more. Of course, that didn’t turn out to be the case. Josh and I, for example, remained and still are as close as ever. Angel and I suffered an estrangement for a few years, but sometimes that’s what success can do to friendships.

  I felt like I had just begun landing lucrative endorsements and turning my press coverage around. People had finally started saying “We love you on Holly’s World” instead of “We loved you on The Girls Next Door.” I was scared that with the show’s cancellation, my positive momentum could be stopped dead in its tracks.

  “JUST DO IT,” my friend advised me. “They’re going to make it whether you want them to or not. You may as well have your voice in there.”

  In 2011, E! executives asked me to film for their True Hollywood Story franchise. I’d been interviewed for the program before, but this time the entire episode was going to be about me! While the idea of having your own E! True Hollywood Story might be a sign to some that you’ve made it, I felt wildly underqualified and the prospect horrified me.

  But I haven’t even accomplished anything yet, I thought. My story wasn’t ready to be told. I hadn’t achieved enough on my own outside of the mansion—and I didn’t want the hour-long program to be a tribute to my days at Playboy. But after talking it out, I realized I didn’t really have a cho
ice in the matter.

  Eventually, I gave the network my cooperation. In retrospect, I feel so sorry for the poor producer forced to interview me. I did not make her job easy. I felt like I had nothing but a trail of mistakes and embarrassments to confess on camera (save for the previous two years), so I was perhaps the grumpiest, bitchiest, most emotional mess that had ever sat down for a THS about her life. The last subject she had interviewed for the series was Katy Perry, who was no doubt upbeat, but she’s someone who’s really accomplished things. I was so insecure—I worried that my life’s story would be presented as that of just another famous-for-nothing Playboy bimbo. Naturally Hef was interviewed for the special (you really think he would miss a chance to be on camera?) and his only real contribution was a chippy remark at my expense.

  “What I thought I had found in Holly, I really found in Crystal,” he had said to the interviewer . . . as if that was in any way relevant my story. He just couldn’t resist an opportunity to belittle me and to make the story all about him.

  But when the special finally aired, something interesting happened: people actually related to me.

  To my surprise, viewers sympathized with my unhappiness and some even said they found the courage to reinvent themselves in their own lives. Inspired by my story, some women told me they were able to remove themselves from difficult situations, get over a breakup, or find the motivation to get healthy. I was and continue to be truly humbled.

  Through these wonderful, honest people, I was able to reevaluate how I viewed my own past and maybe give myself a bit of a break.

  Perhaps sharing my story wasn’t such a bad idea, I thought.

  Maybe I wasn’t defined by the mistakes I had made after all . . . maybe those decisions were what allowed me to become the person I was always destined to be.

 

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