Leighton Meester may be most famous for playing Gossip Girl's Blair Waldorf, the privileged queen bee of the Upper East Side, but Meester's real beginnings were much humbler as she was born while her mother was serving time in prison. But by 10, she'd signed with Wilhelmina Models and appeared in Ralph Lauren ads. By 13, she'd made her TV acting debut on Law & Order. She continued to rack up noteworthy TV credits on Entourage (2004) and 24 (2005) until she donned her first high-society headband on G.G. in 2007. The runaway hit, anchored by the snarky love-hate relationship between Waldorf and Ed Westwick's Chuck Bass which finally ended in a Central Park marriage, kept Meester employed for six seasons and opened her up to big-screen opportunities like Country Strong, The Roommate, Date Night and Monte Carlo. It also allowed her to follow her dream to sing. She sang on the 2009 Cobra Starship single, "Good Girls Go Bad," and dueted with Robin Thicke on "Somebody to Love," while making her solo CD debut. She started dating O.C. sidekick Adam Brody in 2013. The pair, who met in 2011 when they costarred in The Oranges, were engaged in November 2013 and secretly wed three months later.