Leighton Meester

Known for her role as Blair Waldorf in Gossip Girl, Meester has gradually transitioned into starring in films with roles alongside Adam Sandler, Hugh Laurie and Tina Fey. In 2009, Meester turned her sights to music with hits such as "Somebody to Love" with Robin Thicke and "Good Girls Go Bad" with Cobra Starship. The actress is also the face of Vera Wang's fragrance, "Lovestruck." Meester is rumored to be dating her former The Orange co-star, Adam Brody. The actress has won several Teen Choice Awards for her work in Gossip Girl, which ended in 2012.