Holly Madison

Facing credit card debt and potential homelessness, in August 2001, Madison moved into the Playboy Mansion and officially became one of Hugh Hefner's girlfriends. Hefner controlled her finances, enforced a strict schedule and curfew, and denied her opportunities to earn income outside the mansion.[8] In February 2002, after all but two of his girlfriends left, Madison became his "#1 Girl".[4] During her time with Hefner, Madison stated that she wanted to marry him and have his children. However, in an interview at the Playmate of the Year luncheon in May 2008, Hefner said, "I love Holly very much and I think we're going to be together the rest of my life, but marriage isn't part of my puzzle. It's not a personal thing; I just haven't had much luck with marriages."[9] Reflecting on her time at the mansion, Madison has said her feelings for Hefner were attributable to Stockholm syndrome.[8]

On October 7, 2008, Madison announced that her relationship with Hefner had ended, but that she, Bridget Marquardt and Kendra Wilkinson were "still filming stuff together".[10] Hefner confirmed the breakup, saying, "If Holly says it's over, I guess it's over".[11] Madison was later among the former Playmates who spoke out in the docuseries Secrets of Playboy.[12][13]

Madison with then-boyfriend Hugh Hefner in 2008

The Girls Next Door was an E! Network show following life of Madison and others at the Playboy Mansion. Although Madison was never a Playboy Playmate, Playboy published a nude pictorial of Madison with her The Girls Next Door costars in the November 2005 issue. The women were featured again on the covers of the September 2006, March 2008, and February 2009 issues. During seasons three and four, Madison was shown working at the Playboy studios as an intern and later a junior photo editor. She also helped design and put together The Girls Next Door calendars. In February 2009, with the ending of the sixth season she quit working for the company altogether due to her split from Hefner making her position "awkward".[14]

Madison was chosen to replace Jewel on Dancing with the Stars and was partnered with Dmitry Chaplin.[15][16] Madison was injured while practicing[16] and she and Chaplin were voted off.[17]

In May 2009, Madison and Las Vegas Mayor Oscar Goodman led a Guinness World Record-breaking "largest bikini parade ever".[18] According to the Las Vegas Sun, "The politician and the former Playboy house bunny joined forces to usher in the city's summer swimsuit season..." in an event timed to coincide with the 50th anniversary of the Welcome to Fabulous Las Vegas sign.[18] The 281 parade participants broke the prior record of 250.[18] The mark has subsequently been eclipsed by events in the Cayman Islands (331),[19] and Brisbane, Australia (357).[19]

Madison starred in the burlesque show Peepshow at Planet Hollywood in Las Vegas. She was brought in to replace Kelly Monaco after Monaco's three-month contract was up.[20] Madison was likewise initially signed to a three-month contract, but due to the show's success, it was eventually extended to a full year.[21]

Madison starred in her own reality show, Holly's World,[22] which revolved around her life at Planet Hollywood in Las Vegas. "It's all good-natured and not mean like other reality shows", Madison said of her show. "I'm really excited about the new series because I am also getting a legitimate co-producer credit for all the work I do behind the camera. It's not a vanity credit. I'm super excited to learn from the best and take on new responsibilities."[23] The show premiered on December 6, 2009, and ran for two seasons.[24]

In 2021, Madison shared in an interview some of the dark sides of the Playboy lifestyle, as further revealed in 2022 in the A&E documentary series Secrets of Playboy.[25] Madison was the subject of the show's second episode which aired in January 2022.[12] She described, among other things, the Playboy Mansion as "dangerous" and "very cult-like" and accused Hefner of manipulating her in order to advance her career and even attempting to offer her quaaludes during their first sexual encounter in the summer of 2001.[12] She also said that she was often addicted to alcohol during their relationship and that Hefner would often have photographs taken of her and his other girlfriends when they were naked after getting wasted.[12] Madison alleged this enabled him to use blackmail in order to maintain their relationship.[12] She also maintained her previous allegation that she had "Stockholm syndrome" during her relationship with Hefner as well, stating "I definitely thought I was in love with Hef but it was very Stockholm syndrome, very Stockholm syndrome."[12]

In 2015, Madison released her memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.[26] The book details her life in the Playboy Mansion and the beginning of her recovery afterward.[27]

In May 2016, Madison released her second memoir, The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention,[28] which also debuted on the New York Times Best Seller list.[29] The book chronicles her journey toward reinvention and self-acceptance in glamorous Las Vegas.[30]