57 pages 1 hour read

Holly Madison

Down The Rabbit Hole

Nonfiction | Autobiography / Memoir | Adult | Published in 2015

A modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.

Chapters 6-11Chapter Summaries & Analyses

Chapter 6 Summary

In one year, Holly goes from being Hefner’s newest, most junior girlfriend to the one with the most authority and seniority. He replaces all six Mean Girls with new women. Among them is Bridget, who becomes Holly’s fast friend. The new girlfriends have the same obligations and privileges as Hefner's previous entourage. Holly notices, however, that the luster around Hefner’s romantic companionship is not as great as it once was.

Holly and Bridget spend their idle time familiarizing themselves with the mansion’s grounds, and become official tour guides.

Holly, tired of Hefner’s clutter, gains permission to organize his bedroom. It is overflowing with useless objects, some of which are downright creepy. For instance, Hefner made The Guinness Book of World Records for owning more scrapbooks than anyone else in the world. His 2,000 scrapbooks contain photographs of all the women who attended events at the mansion, as well as memorabilia related to every woman he dated. For Holly, these scrapbooks are one manifestation of Hefner’s fixation on celebrity—both his own and that of the people around him.

Playboy Enterprises experiences further financial strain during Holly’s second year as Hefner’s girlfriend. In the hopes of reviving the business, he invites networks to film television specials at the Playboy Mansion. Public curiosity about life behind its gates means they attract many viewers.

For Holly, the most significant of these events was Playboy’s 50th anniversary special, which featured many famous Playmates. It dawns on her that only a handful had enjoyed continued notoriety past their Playboy appearance. “Foolishly,” she writes, “I’d long believed that becoming a Playboy centerfold was the fast-track to fame and fortune. Boy, was I wrong. There have been more than 720 Playmates in Playboy’s history. How many of them can you name[?]” (116). Holly is shaken by the realization that being a Playmate does not translate into either lasting fame or significant fortune.

Holly asks Hefner if he will ever allow her a centerfold pictorial. He tells her she does not have the “look” for one. Instead, he offers her the opportunity to be a Cyber Girl, appearing nude on Playboy’s website.

As the months progress, a new group of Mean Girls forms and begins conspiring against Holly. They are angry that she does not demand more “girlfriend perks” from Hefner. She knows their underhanded plotting against is absurd. Still, it leaves her feeling insecure.

Chapter 7 Summary

Hefner tires of newest Mean Girls and begins banishing them one by one. This means he is in need of more girlfriends.

Any woman who spends time at the mansion has Polaroid photographs taken of her. These are reviewed by Hefner and placed into one of three files: A, B, or C. He perceives “A women” as the most attractive, useful as potential girlfriends and Playmates. He thinks “B women” are also attractive, but not enough to be either girlfriends or Playmates. “C women” are referred to simply as “warm bodies.”

During a special promotion called “Painted Ladies,” Hefner brings in three new women. Holly and Bridget recognize that one of them will become a new girlfriend. Hefner settles on 19-year-old Kendra, and simultaneously ejects the remaining Mean Girls because they tried to give Kendra—a recovering addict—drugs. This leaves Hefner with only three girlfriends: Holly, Bridget, and Kendra.

Kendra, unafraid to ask for what she wants, immediately grabs the spotlight with her spontaneous, unfiltered, childlike behavior. Holly and Bridget work hard to help her understand Hefner’s preferences and procedures, but Kendra is seldom willing to take their advice. As he has done so many times before, Hefner plays his newest girlfriend against her predecessors. This results in predictably awkward confrontations. “When it came to humiliating his girlfriends,” Hefner’s attitude was “the larger the audience, the better” (141).

Over the next year, Bridget and Holly learn to deal with Kendra’s immaturity. On one occasion, while showing off in a nightclub, Kendra knocks hot candle wax onto Holly’s leg, resulting in severe pain. Kendra both fails to apologize and continues to treat Holly rudely. Holly confronts her and later complains to Hefner, who tells Kendra to apologize. In reaction, Kendra breaks down in out-of-control sobs. Hefner has never been critical of Kendra before, and she does not know how to manage her hurt feelings. Following this unhappy episode, the three girls begin to work on bonding.

Chapter 8 Summary

The E! network decides to film a reality television series centered on Hefner’s girlfriends, titled The Girls Next Door. Shortly before filming begins, Hefner announces to Holly that producers are giving each girlfriend a persona: “Kendra is the one who wants to have fun, Bridget is the one who wants a career, and you’re the one who cares about me” (156). About this time, Holly finally sees the Polaroid photograph taken of her during her first trip to the mansion. She recognizes that Hefner must have given her an A-rating. She is surprised because Hefner has always demeaned her as unworthy of a Playboy pictorial.

E! producers do background interviews with all three girlfriends. One of them asks Holly whether Kendra is growing up inside the Playboy Mansion. This is one of the show’s many attempts to transform interpersonal frictions into storylines. Holly gives canned answers to most of their questions, which she has already heard for years.

In one of the few unscripted moments in the series, Hefner tells the three girlfriends that he is going to do a Playboy pictorial as well as a cover shoot with them. All three women react joyfully, as none of them believed they would ever get to live out this dream. Although their nude photo sessions involve a great deal of work, they become one of the girlfriends’ favorite shared memories.

While meeting with a producer, Kendra asks if the women will be paid for starring in the television program. The producer responds, “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’s not about any of you” (165). The show’s attitude to its eponymous stars is that the “girls next door” are replaceable.

One million people tune into see the first episode. The program is a huge hit, with each subsequent episode of the first season garnering 1.5 million viewers. Perhaps because of the way are being treated behind the scenes, Holly, Bridget, and Kendra believe the public perceives them as laughing stocks. In fact, they are gaining real popularity among audiences.

The added stress of the television program deepens Holly’s depression. She asks Hefner if she can see a psychiatrist. He tells her not to get counseling because the doctor will tell her to move out of the mansion. Regardless, she meets with a therapist and begins taking an antidepressant.

Chapter 9 Summary

The Girls Next Door is so successful that E! orders a second season. The women begin giving more input on the program’s production, offering creative ideas about how to focus various episodes. Their show begins bringing in so much money that E! is able to boost the quality of its other programming.

Around this time, Hefner ends the twice-weekly night club trips. To the women’s great relief, the bedroom ritual that always followed clubbing also comes to an end. Moreover, Hefner begins allowing them to travel extensively for the purposes of filming the series.

The Girls Next Door is eventually greenlit for a third season. The women grow closer to one another emotionally. They also continue to offer creative episode ideas, which are well-received by producers.

Following her repeated requests, Hefner finally allows Holly to become an intern photo editor at Studio West, the company that produces images and films for Playboy Enterprises. Holly develops features for new Playmate pictorials. When the head of Studio West retires, creating a vacancy, Holly becomes a permanent employee with the title Junior Photo Editor.

The success of the program brings new attention to Playboy magazine. Hefner decides to do three more cover pictorials with Holly, Bridget, and Kendra.

As Kendra grows more successful, she starts trying to assert her independence. In response, Hefner begins criticizing her the same way he has for years with Holly and Bridget. This strengthens the bond between the three girlfriends.

Chapter 10 Summary

Hefner makes it clear that he does not want the girlfriends to receive royalties from the show. Holly and her fellow girlfriends begin seeking other ways to convert their popularity into economic prosperity. Holly shares ideas for marketing with executives at Playboy Enterprises. They discuss the potential for jewelry and swimsuit lines, although Playboy eventually informs her it will not be pursuing her ideas.

Not long afterward, Holly is horrified to learn that not only is Playboy selling the swimsuits that she suggested, but it is doing so without giving her royalties or even verbal credit for her ideas. She also finds out that Las Vegas casinos are about to start using Girls Next Door slot machines. These should have been a source of revenue for her and the other girlfriends, especially since their images are going to be used. She tells Hefner that the women deserve to be paid to the use of their likeness, but Hefner shuts her down.

Holly wants to appear on NBC’s reality competition, The Celebrity Apprentice. Hefner pronounces this an unworthy idea. However, he goes behind her back and arranges for a different Playmate to appear on The Celebrity Apprentice.

E! greenlights The Girls Next Door for a fourth and then a fifth season. Holly finds certain episodes especially meaningful, including one featuring a trip to her Alaskan hometown and another in which she attends her sister’s wedding in Jamaica.

Yet even as Holly’s abilities, popularity, and age increase—she is now 28 years old—Hefner subjects her to same restrictions on where she can go, how long she can be gone, and with whom she can associate. Hefner refuses to allow Holly and Bridget to attend another Playmate’s wedding in Cabo San Lucas, Mexico, because the celebration naturally involved a party. “You’re not going to any parties,” Hefner says, “The trip to Mexico is off” (203). Holly finds this treatment condescending.

She revisits her notion that she wants to settle down with Hefner and have a family. She learns, after Hefner undergoes a medical test, that he will no longer be able to father children. She realizes that despite her successes and achievements, she is unhappy: Indeed, she has always been unhappy with life in the Playboy Mansion. She states:

I had fallen down a rabbit hole of nasty girls, degrading love life, eroding self-esteem, and total fear of judgment from the outside world [...] I had tried to rationalize my choices by convincing myself that I had fallen in love with Hef and just wanted to settle down and have a family (203).

Holly learns that other women are mistreating a potential Playmate. In the hopes of preventing the would-be Playmate from leaving the Bunny House, Holly takes steps to try and remedy the situation. In response, Hefner screams at her and calls her an unimaginably ugly name for the first time. Holly recognizes that she will never find any happiness in the mansion.

As season five of The Girls Next Door ends, Holly grapples with the fact that soon she will not have the company and support of Bridget and Kendra, either: both women are moving on to other opportunities outside Playboy Enterprises.

Chapter 11 Summary

For the first time since she moved into the Playboy Mansion, Holly finds herself alone. She is in Nevada to supervise a two-day photo shoot, and has convinced Hefner to allow her to remain in Las Vegas overnight rather than making two additional flights.

When the first day’s work concludes, she decides to contact Criss Angel, a well-known Las Vegas magician who had flirted with her and the other girlfriends during an earlier television appearance. She and Criss go to dinner and a club for cocktails. Afterward, Criss accompanies Holly back to her suite, where she wishes him goodnight and he leaves. The next morning, Hefner calls Holly and announces that she has given him the worst night of his life. Hefner secretly had her followed and knows everything that occurred, including the fact that Criss had taken her back to her hotel suite. Though nothing sexual had happened between her and Criss, Holly knows that this is Hefner’s opportunity to demean her as a cheater. Hefner has frequently said that his first wife cheated on him, and he uses this as a pretext to be perpetually unfaithful himself.

Holly recognizes his response as the culmination a pattern that she has experienced since they met. She decides that she will leave Hefner, whom she now recognizes is “just a spoiled child in an old man’s body” (225). Holly moves out of Hefner’s bedroom and into bedroom five as she finishes work on season five of The Girls Next Door.

Hefner unsuccessfully works to manipulate Holly into staying with him. He says that she can have free reign to run season six of The Girls Next Door. He promises to bequeath $3 million to her if she lives with him until his death. He parades a bevy of attractive young women—her potential “replacements”—around, hoping to inspire jealousy. Nothing works. She writes, “Through his vain attempts to intimidate, guilt, persuade, and eventually bribe me, the only thing he succeeded in doing was to convince me that I was making the best decision I had made in a very long time” (229). Holly remains unmoved, recognizing the inherent toxicity of Hefner’s contrived bids for affection.

While she is eager to escape Hefner’s grasp, Holly is sad to bid Bridget and Kendra farewell. Still, it is important that all three women escape this proverbial sinking ship. Despite the success of their show, Playboy Enterprises’ financial status is continuing to deteriorate.

Holly reestablishes ties with Criss, who is delighted to hear she is leaving Hefner. He suggests she move to Las Vegas, where his new show is about to premier. She agrees.

Chapters 6-11 Analysis

The second section of the memoir could be referred to as “The Indentured Servant.” The constant rivalry Holly experiences with the Mean Girls, and the manipulative, often cruel behavior she suffers at Hefner’s hands, slowly kill the impulsive, childlike nature that brought Holly into the mansion in the first place. Her initially vibrant risk-taking personality fades as Holly learns to second-guess her own decisions, comes to believe that her appearance is unacceptable, and speaks with a stammer. Largely in response to the mixed signals and uncertainty she experiences while living with Hefner, Holly decides that she needs to have rhinoplasty. She worries obsessively about the appearance of a tiny dark spot on the back of one of her legs. Though she is the main girlfriend and the object of all of the other girlfriends’ jealousy, Holly does not believe that her position is secure. By way of dealing with her uncertainty, she asks Hefner if she can receive psychiatric counseling. He refuses, though he does allow her to begin to take antidepressants. This is a particularly low time in Holly’s life. She knows that she is miserable, depressed, and sometimes suicidal, but she cannot explain why.

This second section gives readers an intimate look at Hefner, a person Holly comes to believe is actually incapable of intimacy. Hefner burst on the public scene in the early 1950s when, after borrowing $1,000 from his mother, he began publishing Playboy magazine. His stated goal was to glamorize “the girl next door.” Holly later realizes that, for Hefner, this means an emphasis on models that are “just barely legal.” Hefner’s strategy of creating a “classy” pornographic magazine was actually a powerful, subtle tool for women’s objectification. Over the course of 60 years, Hefner institutionalized the objectification of women. His hedonistic Playboy philosophy, as well as his Playboy clubs (which introduced the famous Playboy Bunny), his mansion, his social events, and his well-publicized sexual exploits concealed Hefner’s true nature and intention: using women as objects for the gratification of men. Hefner’s carefully crafted public facade, in which he presented himself as a man who appreciated and celebrated women, is revealed as fictitious behind the mansion’s closed doors.

Hefner loved to bask in public adulation and presented himself as a virile man, irresistible to women. The reality, though, was that women—particularly young, idealistic, naïve women—were not drawn to him because of his sexual prowess, but because he could enhance their careers by giving them Playboy pictorials. Holly presents ample evidence that women quickly departed the mansion once they realized they had no chance at making it into the pages of Playboy. Holly is the exception to this rule. Because Hefner frequently tells her that he loves her, that she is the love of his life, and that he wants to spend the rest of his life with her, Holly emotionally commits herself to him despite the fact that they share no emotional intimacy. They alternate between being roommates and having a contentious father-daughter dynamic. As she wrestles with this reality, she convinces herself that once all of the remaining girlfriends are gone, they will develop a loving relationship.

Adding to the emotional turbulence she feels, when the first set of six Mean Girls all leave the mansion, a second set of Mean Girls arrives almost at once. By this time, it becomes abundantly clear to Holly that Hefner is worsening her negative circumstances by playing the newcomers against her. Holly refers to her adventures in the mansion as Alice in Wonderland and she frames herself as trying to get back to reality alongside Alice. A more apt comparison, however, might be Cinderella, for Holly constantly struggles against evil step sisters with receives no help from her emotionally absent father.

Yet light begins to dawn. First, a new friend and compatriot emerges in the form of Bridget, a new girlfriend. For the first time, it is not Holly alone against the Mean Girls: she has a companion, friend, and ally. The two are not jealous of one another or at odds in any respect. Ironically, the next form of light appears in the form of a television network that wants to cash in on the public’s curiosity about what happens in the Playboy Mansion. Though motived by a desire for viewership, E! network producers quickly recognize that there is more substance to Holly, Bridget, and Kendra than they had imagined. The result is a reality series called The Girls Next Door, which builds upon Hefner’s longtime boast that Playboy was all about glamorizing the “girl next door.”

Initially, the three girlfriends are unaware of the impact their new series has on the network and Playboy. As he did for the previous three years, Hefner continues to manipulate Holly. He shoots down any ideas that would allow the women to have an income from royalties. He watches over the plans for each episode, making certain that he only has to appears in each one briefly, and that no one says anything negative about him or his mansion. The great success of The Girls Next Door, however, means that his girlfriends will travel, encounter other celebrities and entrepreneurs who are interested in their lives, and receive professional offers that will eventually lead them away from the mansion.

Hefner’s hypervigilance and manipulation of Holly lays the groundwork for their relationship’s inevitable demise. When he allows her to spend a night without a chaperone or security, she has supper with an acquaintance without realizing that Hefner has hired people to watch her. As she has been faithful to him, despite his constant infidelity to her, this is the last straw for Holly. She decides that she will be moving out. After she resolutely tells him this, he immediately begins trying to persuade her to stay. Unfortunately, he does not base his request in emotional sincerity, but rather resorts to the same manipulation tactics that pushed Holly away from him in the first place.