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The mark has subsequently been eclipsed by events in the Cayman Islands (331), Brisbane, Australia (357) and Panama City, Florida (450).Madison starred in a topless burlesque show called Peepshow at Planet Hollywood in Las Vegas.In February 2009, with the ending of the sixth season she quit working for the company altogether due to the split from Hefner making her position "awkward." 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.
Madison is also an accomplished author, twice hitting the New York Times best-seller list with “Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny” in 2015, and “The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention” in 2016.
Afterward, Madison moved to Los Angeles and attended Loyola Marymount University.
To afford her college tuition, Holly competed to become a Hawaiian Tropic model and worked as a waitress at Hooters.
She was brought in to replace Kelly Monaco after Monaco's three-month contract was up.
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.
At age two, she lived with her family in Craig, Alaska, on Prince of Wales Island.