She has released two books, Down the Rabbit Hole in 2015, about her life in the Playboy Mansion and her relationship with Hefner, and The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention in 2016.

[4] To afford her college tuition, Madison competed to become a Hawaiian Tropic model and worked as a waitress at Hooters.

[7] 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.

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.

[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".

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".

[17] In May 2009, Madison and Las Vegas Mayor Oscar Goodman led a Guinness World Record-breaking "largest bikini parade ever".

[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.

[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] In 2015, Madison released her memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.

[27] 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.

[28][29] In May 2016, Madison released her second memoir, The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention,[30] which also debuted on the New York Times Best Seller list.