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That same year, Wood played a supporting role in the Andrew Niccol-directed science fiction satirical drama film, Simone, which starred Al Pacino.Wood's breakthrough movie role followed with the 2003 film Thirteen.She played the role of Tracy Louise Freeland, one of two young teens who sink into a downward spiral of hard drugs, sex, and petty crime.Her performance was nominated for a Golden Globe Award as Best Actress - Drama and for a Screen Actors Guild (SAG) Award for Best Actress.One critic commented, "Wood does flip cynicism with such precise, easy rhythms and with such obvious pleasure in naughtiness that she's impossible to hate." In Down in the Valley, which was directed by David Jacobson, Wood's character, Tobe, falls in love with an older man, a cowboy who is at odds with modern society (Edward Norton).Of her performance, it was written that "Wood conveys every bit of the adamant certainty and aching vulnerability inherent in late adolescence." Later in 2006, Wood appeared with an all-star ensemble cast as Natalie Finch in the Golden Globe-nominated 2006 comedy-drama film Running with Scissors.a story of a bipolar jazz musician (Michael Douglas) and his long-suffering teenage daughter, Miranda (Wood), who are reunited after his two-year stay in a mental institution and who embark on a quixotic search for Spanish treasure.One review praised Wood's performance as "excellent".
Wood was awarded the 2007 Cannes Film Festival Chopard Trophy for Female Revelation for her performance.
During the time of Thirteen A supporting role opposite Cate Blanchett and Tommy Lee Jones in Ron Howard's The Missing, in which she played the kidnapped daughter, Lilly Gilkeson, followed the same year, as well as a role in the CSI: Crime Scene Investigation episode "Got Murder? In 2005, Wood appeared in the Mike Binder-directed The Upside of Anger, opposite Kevin Costner and Joan Allen, a well-reviewed film in which Wood played Lavender "Popeye" Wolfmeyer, one of four sisters dealing with their father's absence. Wood's next two starring roles were in dark independent films.
In the 2005 Grand Jury Prize Sundance Film Festival nominee Pretty Persuasion, a black comedy/satirical focusing on themes of sexual harassment and discrimination in schools and attitudes about females in media and society, Wood played Kimberly Joyce, a manipulative, sexually active high-schooler.
The film won the Children's Jury Award at the Chicago International Children's Film Festival Wood made her teenage debut as a leading film actress in 2002's Little Secrets, directed by Blair Treu, where she played aspiring 14-year-old concert violinist Emily Lindstrom.
For that role, she was nominated for Best Leading Young Actress at the Young Artist Awards.
The film won the 2008 Grand Prize at the Ottawa International Animation Festival.