Down The Rabbit Hole

Hugh Hefner (1926-2017) was America’s first celebrity pornographer and one of Holly’s most significant romantic connections. Although his generosity initially saves Holly from serious financial troubles and promises her a more prosperous future, Down the Rabbit Hole eventually frames him as her most powerful antagonist.

The founder of Playboy Enterprises, Hefner mainstreamed pornography use among American men by framing it as a glamorous and “classy” sexual hobby. At its peak, Hefner’s empire included both Playboy and Playgirl magazines, a chain of Playboy Clubs, a line of merchandise, and The Girls Next Door, a reality television program set in the Playboy Mansion. However, the advent of internet pornography and changing cultural mores undercut Playboy’s success.

For many American men, Hefner was an icon: rich, happy, and surrounded throughout his adult life beautiful young women no matter how much he aged. For decades, Hefner carefully advanced a public narrative that these were women were attracted to him because of the lifestyle and opportunities that he could supply. Known for his friendships with A-list celebrities and the lavish parties he would host at the Playboy Mansion, Hefner intentionally portrayed himself as the man every woman wanted to be with and someone every man wanted to be.

Down the Rabbit Hole contradicts Hefner’s personal mythology, portraying him as a highly manipulative misogynist less interested in celebrating women’s bodies than in cruelly judging them by his arbitrary beauty criteria. Moreover, he is a disappointing lover—impotent without Viagra—whose obsession with personal celebrity parallels Narcissus’s fixed gaze on himself. The narrative frames his sexual depravity and inability to love anyone else as a dysfunctional reaction to his first wife’s infidelity.

Hefner experiences no character growth throughout the book. By the time it ends, Hefner’s mansion has fallen into disrepair, he is drowning in useless memorabilia, and Holly, Bridget, and Kendra have all left him. Their departure is a true loss for Hefner, as they were not only his most harmonious trio of girlfriends, but also the reason that his last significant professional endeavor, The Girls Next Door, was a success. The girlfriends he brings in to replace them have a ghastly penchant for infighting and are so unpopular that E! cancels The Girls Next Door. As the show ends, the fortunes of Playboy Enterprises are floundering more than ever before. In 2011, at the age of 85, Hefner finally gives up and sells his stake in Playboy Enterprises in exchange for a $1 million annual salary and the right to live out his life in the Playboy Mansion.

Hefner’s hoarding of meaningless objects and relationships is ultimately his undoing. He dies surrounded by cheap Polaroid photographs of every woman to have ever stepped foot in the mansion, married to someone he has had to pay to stay with him. His widow, Crystal Hefner, later publishes a memoir in which she reflects on the trauma of his manipulation, titled Only Say Good Things: Surviving Playboy and Finding Myself (2024).

Criss is a professional magician with a long-term Las Vegas show. Wealthy and handsome, Criss flirts with Holly the first time they meet. After she leaves Hefner and the mansion, Criss immediately steps in to fill the emotional void in her life. Intent on gaining Holly’s affections, he spends nearly all of his waking hours with her, lavishing her with expensive gifts and seducing her with promises that they will raise a family together.

Unfortunately, Holly discovers that Criss is as obsessively jealous and controlling as Hefner. Criss demands Holly total devotion and attention, pressures her to give up professional opportunities, and baselessly accuses her of cheating. His volcanic temper causes her to fear that Criss will become violent. Near the end of their connection, he has become so controlling that she must deceive him to safely sneak away. In response, he threatens to prevent her from ever working in Las Vegas.

The character of Criss is important because he inadvertently provides Holly with the chance to demonstrate how strong she has become: Whereas her escape from Hefner is partially abetted by Criss, her escape from Criss is independently planned and self-executed.

Near the outset of Down the Rabbit Hole, emotional and financial pressures force Hefner to go from seven to three live-in girlfriends. Holly, Bridget Marquardt, and Kendra Wilkinson survive his entourage purge and shoot a Playboy special for the E! network shortly thereafter. It draws enough viewers that Hefner and E! agree to film a reality show, The Girls Next Door, around the girlfriends’ lives. Each woman is assigned an on-camera persona: Holly is nurturing, Kendra is fun-loving, and Bridget is career-driven. The series seeks to hook the curiosity of those interested in the relationships of the three girlfriends with one another and how they lived in the (theoretically) uninhibited atmosphere of the Playboy Mansion. The women are disrobed for much of the filming, with their nudity blocked out for American audiences, although not for international viewers.

Despite the fact that this series is successful, drawing some of E!’s largest audiences, the women are not paid for their work on the first season. However, as the program continues to draw viewership over the next five years, the three begin to receive payment for their work. They are also given the chance to offer creative input.

While the three “Girls Next Door” enjoy working together and develop shared interests, there are real distinctions between them. From their initial acquaintance, Holly and Bridget are close friends. Bridget is the only potential rival for whom Holly has no negative comments. Like Holly, Bridget is career-minded and looks forward to the day she can permanently leave the Playboy lifestyle behind. In contrast, Holly portrays Kendra as an immature, unfiltered young woman who acts out histrionically on a regular basis. One benefit of Kendra’s personality, though, is that she is willing to spontaneously speak the truth about circumstances that Holly and Bridget avoid addressing.