Film career:Stiles's first film was a non-speaking part in I Love You, I Love You Not (1996), with Claire Danes and Jude Law. She also had small roles as Harrison Ford's daughter in Alan J. Pakula's The Devil's Own (1997) and in M. Night Shyamalan's Wide Awake (1998). Her first lead was in Wicked (1998), playing a teenage girl who might have murdered her mother so she could have her father all to herself. Critic Joe Balthai wrote she was "the darling of the 1998 Sundance Film Festival" and Internet movie writer Harry Knowles said she was the "discovery of the fest", but the film was not commercially released in the U.S. and went direct-to-video.
In 2001, after Stiles had become better known the role that gained Stiles renown was Kat Stratford, opposite Heath Ledger, in Gil Junger's 10 Things I Hate About You (1999), an adaptation of The Taming of the Shrew set in a high school in Tacoma, Washington. She won an MTV Movie Award for "Breakthrough Female Performance" for the role, and the Chicago Film Critics voted her the most promising new actress of the year. Foreign critics applauded her work as well, including Adina Hoffman, who praised her as "a young, serious looking Diane Lane" and Martin Hoyle, who commented that Stiles played Kat "with bloody-minded independent charm from the beginning with hints of wistfulness beneath the determination."
Her next starring role was in Down to You (2000), which was panned by critics, but earned Stiles and her co-star Freddie Prinze, Jr. a Teen Choice Award nomination for their on-screen chemistry. She subsequently appeared in two more Shakespearean adaptations. The first was as the Ophelia in Michael Almereyda's Hamlet (2000), with Ethan Hawke in the lead. The second was in the Desdemona role, opposite Mekhi Phifer in Tim Blake Nelson's O (2001), a version of Othello set in a private boarding school. Neither film was a great success; O had been subjected to many delays and a change of distributors, and Hamlet was an art house film shot on a minimal budget.Stiles's next commercial success was in Save the Last Dance (2001), as an aspiring ballerina forced to leave her small town in downstate Illinois to live with her struggling musician father in Chicago after her mother dies in a car accident. At her new, nearly all-black school, she falls in love with the character played by Sean Patrick Thomas, who teaches her hip-hop dance steps that get her into The Juilliard School. The role won her two more MTV awards for "Best Kiss" and "Best Female Performance", and a Teen Choice Award for best fight scene for her battle with Bianca Lawson. Rolling Stone pronounced her "the coolest co-ed," putting her on the cover of its April 12, 2001 issue. She told Rolling Stone that she performed all her own dancing in the film, though the way the film was shot and edited might have made it appear otherwise.
In David Mamet's State and Main (2000), about a film shooting on location in a small town in Vermont, she played a teenage girl who seduces a film actor (Alec Baldwin) with a weakness for young girls. Stiles also played opposite Stockard Channing in the dark art-house film The Business of Strangers (2001) as a conniving, amoral secretary who exacts revenge on her boss. Channing was impressed by her co-star: "In addition to her talent, she has a quality that is almost feral, something that can make people uneasy. She has an effect on people." Stiles also had a small but crucial role as Treadstone operative Nicolette "Nicky" Parsons in The Bourne Identity (2002), a role that was enlarged in The Bourne Supremacy (2004), then greatly expanded in The Bourne Ultimatum (2007).Between the Bourne films, she appeared in Mona Lisa Smile (2003) as Joan, a student at Wellesley College in 1953, whose art professor (Julia Roberts) encourages her to pursue a career in law rather than become a wife and mother. Critic Stephen Holden referred to her as one of cinema's "brightest young stars," but the film met with generally unfavorable reviews.
Stiles played a Wisconsin college student who is swept off her feet by a Danish prince in The Prince and Me (2004), directed by Martha Coolidge. Stiles told an interviewer that she was very similar to the character, Paige Morgan. Critic Scott Foundas said while she was, as always, "irrepressibly engaging," the film was a "strange career choice for Stiles." This echoed criticism in reviews of A Guy Thing (2003), a romantic comedy with Jason Lee and Selma Blair. Critic Dennis Harvey wrote that Stiles was "wasted," and Stephen Holden called her "a serious actress from whom comedy does not seem to flow naturally".In 2005, Stiles was cast opposite her Hamlet co-star Liev Schreiber in The Omen, a remake of the 1976 horror film. The film was released on June 6, 2006.
She returned to the Bourne series with a much larger role in The Bourne Ultimatum in 2007, and to this day it is her highest grossing film. Producer Lynda Obst said that Stiles was "turning into the next Meryl Streep." She will next work on a film adaptation of The Bell Jar, which coincidentally was a book her character was seen reading in her breakthrough film 10 Things I Hate About You. Stiles also appears in the forthcoming film Gospel Hill. She will act in the role of a woman who falls in love with her stalker in the upcoming thriller Cry of the Owl, based on the novel by Patricia Highsmith. In May 2010 was casted for a major role in Dexter.
