Holly Madison was born as Hollin Sue Cullen on December 23, 1979 in Astoria, Oregon. She studied at the Portland State University with psychology and theatre as majors. In 1999, Holly continued her studies at the Loyola Marymount University in Los Angeles. She worked at Hooters to pay for college tuition, but when she competed at a Hawaiian Tropic model search and won, everything changed. As Holly Madison worked as a Hawaiian Tropic model, one of Hugh Hefner’s friends saw her and included her on the Playboy Mansion’s party list. She attended a year of parties, before Hugh invited her to move into the mansion.

By August 2001, Holly Madison became one of Hef’s seven official girlfriends. The following year, when two of Hef’s girlfriends left the mansion, Madison became his #1 Girl. Aside from being Hugh Heffner’s main girl, Holly also starred alongside Hef’s other girlfriends Kendra Wilkinson and Bridget Marquardt on the reality TV show “The Girls Next Door” from 2005 to 2009. The three girls also appeared on the Playboy magazine on November 2005, for September 2006, March 2008 and February 2009 to promote their show.

Holly Madison has also worked behind the cameras. After serving as an intern for Playboy studios, she became a junior photo editor and took over responsibilities such as choosing Playmate candidates, directing photo shoots and assisting in designing pictorials. Holly Madison also co-authored a book with Wilkinson and Marquardt entitled “The Girls Next Door.”

Outside Playboy, Holly Madison has appeared on TV shows such as “Entourage,” “General Hospital,” “The Apprentice” and “Curb Your Enthusiasm.” She also landed minor roles in the comedy movies “The House Bunny” and “Scary Movie 4.” In 2009, Holly Madison joined the “Dancing with the Stars” competition and landed her own reality show called “Holly’s World,” wherein she also serves as the show’s co-producer.

In 2008, Holly Madison was named the #1 Hooters girls of all time at the restaurant’s 25th anniversary. That same year, she began dating illusionist Criss Angel, but broke off the relationship in February 2009. By the end of 2009, Holly Madison was seen dating Good Charlotte guitarist Benji Madden. They split on January 2010.