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.
Meester dons headbands and slathers on the lip-gloss to play vengeful Queen Bee, Blair Waldorf, in Gossip Girl, The CW's adaptation of the juicy novels by Cecily von Ziegesar. The teen soap follows a group of rich New York City Upper East Siders. "People who live in that world are going to blush and be very bashful about how true to life it is," Meester (pictured with Chace Crawford) says. The series costars Blake Lively (Blair), Penn Badgley (Dan), Ed Westwick (Chuck) and Taylor Momsen (Jenny).
As Gossip Girl becomes TV's favorite guilty pleasure, Meester becomes a style star off-camera with costar Blake Lively (right). "I wish I had the money for style like that," Meester tells WWD of her character's luxe wardrobe. "Everything she wears is exactly appropriate to where she's going, and it's important for her to stand out but look dignified." Adds costume designer Eric Daman, "These girls are very into fashion. They know what's going on and we're just trying to keep it contemporary."
The cast of Gossip Girl strips down for a tantalizing cover of New York magazine, which calls the teen soap, "the most awesomely awesome show ever." The magazine says of Meester, "Her villain-you-want-to-root-for is the most sophisticated performance on the show." That week, the entire cast also lands on PEOPLE's Most Beautiful List.
Gossip Girl's reigning king and queen, Meester and Westwick become the heart of GG with their love-hate relationship in the drama's second season. EW dubs their performances two of 2008's 15 greatest. "You can't put a finger on what makes two characters connect," Westwick says. "It's just chemistry. We have it. We feel it." Meester agrees, telling Teen Vogue, "He's my favorite actor to work with."
Meester and Lively score the cover of Rolling Stone, where she reveals that GG producers originally thought she was "too kind and sweet" to play Blair. But the actress refused, saying, "It felt like mine." On the music front, the aspiring singer releases the hit, "Good Girl Go Bad," with the band Cobra Starship – and makes moves on her solo debut, with the single, "Somebody to Love," with Robin Thicke.
Meester lends her pipes to the role of rising country star Chiles Stanton in Country Strong, costarring Gwyneth Paltrow, Tim McGraw and Garrett Hedlund. "Just being in Nashville and working there and meeting the most incredible musicians and producers and songwriters and singers…was really cool," she tells MTV. "I have this newfound appreciation for that style of music."
Meester plays college roommate-from-hell Rebecca opposite Minka Kelly in The Roommate, an updated take on Single White Female, which opens at No. 1. "At times on set I was a little concerned whether or not she was there because she scared me so much!" Kelly tells Nylon of Meester's dedication. "The look in her eye was so surreal. I was in awe at how much she committed to it."
BIOGRAPHY (top to bottom): CW; Andy Fossum/Startraks; courtesy New York Magazine; Courtesy of Rolling Stone; Sony; Everett