From prison to the Upper East Side, the young Leighton Meester has lived quite a life already! Born while her mother was serving time in jail, Leighton signed with Wilhemina Models at the age of ten and began acting three years later. While the starlet landed guest spots on Entourage and 24, it was her role as Blair Waldorf on The CW smash hit Gossip Girl that shot Leighton to superstardom. Never without her signature headband and scheming ways, Leighton's portrayal of Queen Bee provided the teen soap with the perfect villian everyone hated to love. In 2009, Leighton was featured singing on the Cobra Starship song "Good Girls Go Bad" and released her debut solo album. Two years later, Leighton made her move to the big screen opposite Gwyneth Paltrow in Country Strong and showed off her range in the college thriller The Roommate.