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Other film roles include Ang Lee’s The Ice Storm (1997), the comedy-drama Wonder Boys (2000), the thriller Abandon (2002), the dark comedy Pieces of April (2003), Christopher Nolan’s Batman Begins (2005), in which she portrayed Rachel Dawes, the comedy satire Thank You for Smoking (2006) and the horror film Don't Be Afraid of the Dark (2011).She has also played on Broadway in a production of Arthur Miller's All My Sons, and had numerous guest roles on television programs such as How I Met Your Mother.The Toledo Blade reported she was offered the lead in Buffy the Vampire Slayer but she never turned it down. The fact that she is drop-dead gorgeous didn't hurt either." During her time as a series regular on Dawson's Creek, Holmes first leading role in a film came in 1998's Disturbing Behavior, a Scream-era Stepford Wives-goes-to-high school thriller, where she was a loner from the wrong side of the tracks.Columbia Tri-Star Television, producer of a new show named Dawson's Creek that was created by screenwriter Kevin Williamson, asked her to come to Los Angeles to audition, but there was a conflict with her schedule. The film was recut from what the director intended.The Hollywood Reporter critic called her character, Samantha Mackenzie, "a startling example of how a studio film can dumb down and neutralize the comic abilities of a lively young star." In the 2005 film Batman Begins she played Rachel Dawes, an attorney in the Gotham City district attorney's office and the childhood sweetheart of the title character. "Holmes is OK", was its critic's sole remark on her performance.She also appeared in the film version of Christopher Buckley's satirical novel Thank You for Smoking about a tobacco lobbyist played by Aaron Eckhart, whom Holmes's character, a Washington reporter, seduces.Holmes hosted Saturday Night Live on February 24, 2001, participating in a send-up of Dawson's Creek where she falls madly in love with Chris Kattan's Mr.Peepers character and singing "Big Spender" from Sweet Charity.

Eventually, Holmes was signed to an agent after performing a monologue from To Kill a Mockingbird. Holmes read for the part of Joey Potter, the tomboy best friend of the title character Dawson, on a videotape shot in her basement, her mother reading Dawson's lines. She first achieved fame for her role as Joey Potter on The WB television teen drama Dawson's Creek from 1998 to 2003.