At 10, Meester–who was born while her mother was serving time in prison–signs with Wilhelmina Models and appears in Ralph Lauren ads. At 13, she makes her TV acting debut on an episode of Law & Order.
Meester plays virginal pop singer Justine Chapin on the HBO hit Entourage. In the episode, Jessica Alba – who appears as herself – invites the boys to a party she's throwing for Meester's character, who flirts with movie star Vince Chase (played by Adrian Grenier, left).
Meester racks up TV credits with Fox's 24 as Debbie Pendleton (right) in the acclaimed show's fourth season. She plays the American girlfriend of Behrooz Araz (played by Jonathan Ahdout) and gets poisoned by Araz's mother in her four episode-run.