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Madison was born Holly Cullen in Astoria, Oregon. Her father traveled around due to work in the timber industry, and from age 2-11, she grew up on Prince of Wales Island, Alaska, near Ketchikan. Her family then moved back home to St. Helens, Oregon. She attended Portland State University for two years as a double-major in theatre and psychology.
In 1999, Madison moved to Los Angeles to attend Loyola Marymount University, where to make money she competed to become a Hawaiian Tropic model and worked at Hooters. This led to invitations to the Playboy Mansion, at a time when Hefner had seven other girlfriends. Madison moved into the mansion and became one of Hefner's official girlfriends in August 2001, after more than a year of visiting the mansion. In February 2002, after all but two of his girlfriends left, Madison became Hef's '#1 Girl' and moved into his bedroom at the mansion. Hefner's two other girlfriends, Bridget Marquardt and Kendra Wilkinson, have their own bedrooms down the hallway. In 2008 after her Playboy success she was named among the top Hooters girls of all time in 2008 as part of the restaurant's 25th anniversary.
Madison has spoken openly about her plastic surgery, having had a rhinoplasty (nose job) and breast augmentation, going from an A cup breast to a D cup.
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