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"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. I'm super excited to learn from the best and take on new responsibilities." In 2015, her memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny (ISBN 978-0-06-237210-9) was published.The book reveals exploits from living in the Playboy Mansion and discusses relationships with Hugh Hefner, Bridget Marquardt, and Criss Angel, among others.Her appearance at these venues led to invitations to Hefner's Playboy Mansion and at the age of 21, after more than a year of such visits, Madison was invited to move in.The show starring Holly and her two co-stars' life at the Playboy Mansion was an instant hit for E! Although not a Playboy Playmate, the initial success of the show was so great that Playboy published a nude pictorial of Madison, with her Girls Next Door costars, Bridget Marquardt and Kendra Wilkinson in the November 2005 issue.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 July 2015, Madison released her first book and memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
To afford her college tuition, Holly competed to become a Hawaiian Tropic model and worked as a waitress at Hooters.
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 2007, 2008, and 2009 calendars.
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." According to the Las Vegas Sun, "The politician and the former Playboy play thing 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.