Madison was born Holly Cullen in Astoria, Oregon. Her father traveled around due to work in the timber industry, and from ages two through eleven, 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. To afford college tuition, she competed to become a Hawaiian Tropic model and worked at Hooters. Becoming noticed, this led to invitations to the Playboy Mansion. After more than a year of visiting the mansion, Madison was invited to move in and became one of Hefner's seven official girlfriends in August 2001. After all but two of his girlfriends had left in February 2002, 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. After all of her Playboy success, she was named among the top Hooters girls of all time in 2008 as part of the restaurant's twenty-fifth anniversary.
Madison has spoken openly about her plastic surgery, having had a rhinoplastybreast augmentation, going from a size A-cup breast to a D-cup.lower back tattoo of the Playboy Bunny. (nose job) and She has a
She also has been chosen to replace Jewel Kilcher on Dancing with the Stars after Kilcher was forced to withdraw (along with Nancy O'Dell) due to injuires sustained during rehearsal. She will be partnered with Dmitry Chaplin.
In 1999, Madison moved to Los Angeles to attend Loyola Marymount University. To afford college tuition, she competed to become a Hawaiian Tropic model and worked at Hooters. Becoming noticed, this led to invitations to the Playboy Mansion. After more than a year of visiting the mansion, Madison was invited to move in and became one of Hefner's seven official girlfriends in August 2001. After all but two of his girlfriends had left in February 2002, 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. After all of her Playboy success, she was named among the top Hooters girls of all time in 2008 as part of the restaurant's twenty-fifth anniversary.
Madison has spoken openly about her plastic surgery, having had a rhinoplastybreast augmentation, going from a size A-cup breast to a D-cup.lower back tattoo of the Playboy Bunny. (nose job) and She has a
She also has been chosen to replace Jewel Kilcher on Dancing with the Stars after Kilcher was forced to withdraw (along with Nancy O'Dell) due to injuires sustained during rehearsal. She will be partnered with Dmitry Chaplin.
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