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In August 2001, Holly moved into the Mansion and officially became one of Hefner's girlfriends.In February 2002, after all but two of his girlfriends left, Madison became his "#1 Girl." During her time with Hugh Hefner, Madison stated that she wanted to marry him and have his children.

"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. I'm super excited to learn from the best and take on new responsibilities." The show premiered with a "preview episode" on December 6, 2009, and ran for two successful seasons.The women were featured again on the covers of the September 2006, March 2008, and February 2009 issues.In the Season 3 episode "Girls Next Door," Madison stated that she wanted to have a career producing Playboy spreads.In May 2014 Madison opened a speakeasy-themed club, 1923 Bourbon and Burlesque, at the Mandalay Bay hotel in Las Vegas.In 2015, her memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, was published.

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