Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny is a memoir of early-21st-century life in the Playboy Mansion, narrated by Holly Madison, the former “main girlfriend” of the late Hugh Hefner, founder of Playboy Enterprises. Over seven years, Holly experiences bitter rivalry with other girlfriends and private denigration by Hefner, even as he publicly declares his love. Holly becomes a budding reality TV star and ultimately a sought-after Las Vegas entertainer. The core theme of her story is discovery, not only of the grim realities behind the Playboy Mansion’s glamorous façade, but also of her own inner resilience, personal talents, and well-deserved capacity self-confidence and self-esteem. A New York Times #1 bestseller, Madison’s memoir was originally published in 2015.

This guide references the Dey Street 2016 paperback edition.

Content Warning: Down the Rabbit Hole depicts women’s objectification, sex work, explicit scenes of sexual intercourse, infidelity, substance abuse, and suicidal ideation. Obscene language occurs throughout the source text and is used to demean women. To ensure factual accuracy, this guide engages with all of these aspects of the source text. It also includes background context involving bestiality and relational abuse.

Summary

As a child, Holly idolizes Marilyn Monroe, whom she sees as emblematic of glamor and fame and she hopes to become a Hollywood actor. She becomes familiar with the Playboy Playmates thanks to the Playboy magazines that regularly arrive at her home.

As a college student in Portland, Oregon, Holly auditions to be Playboy’s Millennial Playmate. Holly decides to drop out of college and move to Los Angeles to pursue an acting career. To support herself, she works as a server for the Hooters restaurant chain and models for the Hawaiian Tropic® skincare brand.

At a gathering of models, Holly meets Hugh Hefner’s personal physician, who invites her to a pool party at the Playboy Mansion. She encounters Hefner there, but it will be a full year before she has another personal interaction with him.

Holly becomes a regular at the Sunday pool parties. She is eventually invited to attend one of the twice-weekly club nights hosted by Hefner and his girlfriends. Currently, there are only six girlfriends living in the mansion, meaning there is room for one more. Her first evening at the club, she must decide whether to engage in sexual intercourse with Hefner; a requirement if she wants him to consider her for the “open girlfriend spot.” She does so. The next day, Holly moves out of her apartment and into the Playboy Mansion. This brings her into a world of jealousy, dishonesty, and bitter rivalry between herself and the other girlfriends.

At the end of her sixth month in the mansion, Hefner asks Holly if she would like to be his “main girlfriend,” and the other girlfriends offer Holly a measure of superficial respect, though they are mostly insincere and untrustworthy. Holly develops only one close friendship with a new girlfriend named Bridget Marquardt. Holly collectively nicknames the other women the “Mean Girls.”

Holly is troubled by the Mean Girls’ backbiting, as well as Hefner’s demeaning treatment. He criticizes her physical appearance and tells her that she is unworthy of her own Playboy pictorial. Over time, she realizes that even though Hefner claims he wants his girlfriends to exist peacefully, he actually creates conflict in a deliberate strategy that forces them to compete among themselves for Hefner’s attention and approval. Holly’s self-esteem suffers, and she is sometimes depressed to the point of feeling suicidal. She develops a stammer and firmly believes she is unattractive. She asks Hefner to pay for a rhinoplasty.

Hefner discovers that the Mean Girls are selling invitations to his exclusive parties. The first set of Mean Girls leaves the mansion, only to be replaced by a second set of women who are equally untrustworthy. Eventually, Hefner removes these women from the mansion, too, leaving only Holly, Bridget, and a newcomer named Kendra Wilkinson.

Aware of the public interest in what happens at the Playboy Mansion, Hefner works with reality TV networks like E! to film the Playmates. Hefner requires that producers depict everyone involved as content with their living arrangement. E! producers recognize that the three girlfriends are individuals with unique backstories, hopes, and dreams and the TV series The Girls Next Door is born. The first year of the series is a great hit for the network, which promptly orders a second year. Playboy gives the three girlfriends a pictorial, along with the first of four covers. They are paid for the photographs, although they receive no money for their first year as television stars. The producers tell them this is because it is Hefner’s show and they are easily replaceable. The program continues for five years, growing in popularity. However, the girlfriends remain largely unaware of this popularity because they live such an insular existence. Producers fill the series with pretense: Despite the fact that Hefner is its alleged star, he typically appears for only a few minutes in each episode.

Holly becomes an intern at Studio West, the production company that recruits and photographs Playmates. Soon she has a permanent position there, where she is recognized for her professionalism. For the first time, Hefner allows her to travel from the mansion overnight to oversee a photo shoot in Las Vegas. There, she has dinner with magician Criss Angel. The next morning, Holly finds out that Hefner secretly had her followed and he accuses her of cheating on him, which is untrue. Holly decides to move out of the Playboy Mansion. Around the same time, both Bridget and Kendra accept outside career offers, and they also leave the mansion. This leaves Hefner with no girlfriend.

Hefner works diligently to discourage Holly from leaving, but once she moves out, he immediately has three new girlfriends move into the mansion. Holly moves to Las Vegas, where she has a brief relationship with Criss, who says he wants to marry her. Unfortunately, Holly discovers that he is just as controlling as Hefner. Even worse, Criss grows increasingly violent. She moves on quietly, going to Portland to see her family, then returning to Los Angeles. Shortly thereafter, she becomes a contestant on Dancing With the Stars. This makes her financially independent and while on the show, she learns that a Vegas burlesque act, Peepshow, needs to cast a new lead. It offers her a three-month contract to be the star. As she prepares for this role, she is subjected to criticism and attempted sabotage from Hefner, Criss, and Criss’s new girlfriend. Holly’s work in Peepshow is so successful that her contract is extended for years.

She begins a new reality program with E! called Holly’s World, which is intended to show what life is like in Las Vegas. The ratings are higher than those for The Girls Next Door. After two years of Holly’s World, the new president of E! decides to cut all references to Playboy and ends the Holly’s World reality show.

Holly continues to be the lead actor in Peepshow, and acquires more responsibilities each year. After four years, she decides that she will leave the show while it is still one of the top-rated performances on the Las Vegas strip. About that same time, she meets Pasquale Rotella, an entertainer who owns a carnival. They fall deeply in love. Shortly before her Peepshow contract ends, she discovers that she is expecting. She holds her last performance when she is five months pregnant. Her baby, Rainbow Aurora, is born in the spring of 2013. That fall, she and Pasquale get married in a ceremony at Disneyland.