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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.

Stiles also appeared 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.

and her a Teen Choice Award nomination for their on-screen chemistry.Stiles later transitioned to more adult roles, garnering a nomination for the Satellite Award for Best Supporting Actress – Motion Picture for her performance in The Business of Strangers (2001), Mona Lisa Smile (2003), and The Omen (2006).She became known to a wider audience for her supporting role alongside Matt Damon as Nicky Parsons in the Bourne film series (2002–2016).She had a recurring role as Lumen Pierce in the fifth season of the Showtime series Dexter (2010), a role that earned her 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.

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