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Stiles told an interviewer that she was very similar to her character Paige Morgan.Critic Scott Foundas said while she was, as always, "irrepressibly engaging", the film was a "strange career choice for Stiles".Rolling Stone pronounced her "the coolest co-ed", putting her on the cover of its April 12, 2001, issue.In David Mamet's State and Main (2000), about a film shooting on location in a small town in Vermont, she played a teenaged girl who seduces a film actor (Alec Baldwin) with a weakness for teen girls.From July to August 2002, she performed on stage in Eve Ensler's The Vagina Monologues, She returned to Saturday Night Live on May 5, appearing as then-President George W.Bush's daughter Jenna Bush in a skit that poked fun at the two first daughters for being arrested for underaged drinking.She had a recurring role as Lumen Pierce in the fifth season of the Showtime series Dexter (2010), a role that earned her nominations for the Golden Globe Award for Best Supporting Actress – Series, Miniseries or Television Film and the Primetime Emmy Award for Outstanding Guest Actress in a Drama Series.As a member of the cast of Silver Linings Playbook (2012), Stiles was nominated for a Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture.
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.
The Chicago Film Critics voted her the most promising new actress of the year.
Her next starring role was in Down to You (2000), which was panned by critics, but earned her co-star Freddie Prinze, Jr.
Her first film role was in I Love You, I Love You Not (1996), followed by a leading role in the thriller Wicked (1998), for which she was awarded the Karlovy Vary International Film Festival Award for Best Actress.
She went on to gain prominence for her lead roles in teen films such as 10 Things I Hate About You (1999) for which she won MTV Movie Award for Best Breakthrough Performance and was nominated for two Teen Choice Awards, Down to You (2000), for which she was nominated for another two Teen Choice Awards, and Save the Last Dance (2001), winning the Teen Choice Award for Choice Movie Actress and was nominated for the MTV Movie Award for Best Female Performance.