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In 2003, Madison was the subject of a Playboy Cyber Girl of the Week pictorial on the magazine's website.
She also appeared on the cover and inside of the November 2005 issue of Playboy, along with Marquardt and Wilkinson, as part of a special pictorial promoting The Girls Next Door.
"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 it started airing regularly in June 2010.
Madison was chosen to replace Jewel Kilcher on Dancing with the Stars after Kilcher was forced to withdraw (along with Nancy O'Dell) due to injuries sustained during rehearsal. On March 31, 2009 Holly and Dmitry were voted off the show in a double elimination episode.
Madison stars in topless burlesque show Peepshow at Planet Hollywood in Las Vegas.
In the past, Madison has stated that she wanted to marry Hefner and have his children.
Madison's appearance at these venues led to invitations to Hefner's Playboy Mansion.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.After more than a year of such visits, Madison was invited to move in.She became one of Hefner's seven official girlfriends in August 2001.