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The film, written by Charlie Kaufman and directed by Michel Gondry, follows a female naturalist, played by Patricia Arquette.
Duff played the younger version of Arquette's character.
In November 2008, she released a compilation of her greatest hits, Best of Hilary Duff, whose single "Reach Out" became her third #1 on the Billboard Hot Dance Club Play.
Duff has also branched into fashion by launching her own clothing lines, Stuff by Hilary Duff and Femme for DKNY Jeans, and two exclusive perfume collections with Elizabeth Arden.
The same year, Duff recorded a cover version of Brooke Mc Clymont's "I Can't Wait" for the Lizzie Mc Guire soundtrack, and "The Tiki Tiki Tiki Room" for the first Disney Mania compilation album.
Her first album was Santa Claus Lane (2002), a collection of Christmas songs that included duets with her sister Haylie, Lil' Romeo, and Christina Milian. In 2003, Duff received her first major role in a feature film when she was cast alongside Frankie Muniz in Agent Cody Banks.
Duff's early career was marked by playing minor roles, starting off with an uncredited appearance in Hallmark Entertainment's western miniseries True Women in 1997.
The film was released to mostly unenthusiastic reviews.
Accompanied by the Disney Channel-only single "Tell Me a Story (About the Night Before)", it peaked at 154 on the U. The film received positive reviews and was successful enough to spawn a sequel, in which Duff did not participate.
The same year, Duff reprised her role as Lizzie Mc Guire for The Lizzie Mc Guire Movie. Later that year, she starred in the film Raise Your Voice, her first role in a drama film.
As of October 2010, her upcoming films include, Bloodworth and The Story of Bonnie and Clyde.
Duff has since expanded her repertoire into pop music with the release of three RIAA-certified platinum albums and over thirteen million records sold worldwide as of February 2007.