Relationship with Hugh Hefner and Playboy 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. In February 2002, after all but two of his girlfriends left, Madison became his "#1 Girl". Reflecting on her time at the mansion, Madison claimed that her feelings for Hefner were attributable to
Stockholm syndrome. Hefner confirmed the breakup, saying, "If Holly says it's over, I guess it's over". Madison was later among the former Playmates who spoke out in the docuseries
Secrets of Playboy.
2005–2009: The Girls Next Door in 2007
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".
After The Girls Next Door Madison was chosen to replace
Jewel on
season 8 of
Dancing with the Stars and was partnered with
Dmitry Chaplin. She and Chaplin were voted off in a double elimination, ultimately placing 11th. In May 2009, Madison and Las Vegas Mayor
Oscar Goodman led a
Guinness World Record-breaking "largest bikini parade ever". 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. and
Brisbane, Australia (357). 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.
2009–2011: ''Holly's World'' Madison starred in her own reality show, ''
Holly's World'', 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." The show premiered on December 6, 2009, and ran for two seasons.
2022: Secrets of Playboy 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. Madison was the subject of the show's second episode which aired in January 2022. The book details her life in the Playboy Mansion and the beginning of her recovery afterward. She alleged, among other things, that the environment she experienced while at the mansion was a "twisted world" that led to her being tempted to commit suicide. In May 2016, Madison released her second memoir,
The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention, which also debuted on the
New York Times Best Seller list. The book chronicles her journey toward reinvention and self-acceptance in glamorous Las Vegas. ==Personal life==