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Duff subsequently ventured into feature films, with many successful movies to her credit including The Lizzie Mc Guire Movie, Cheaper by the Dozen, A Cinderella Story and Cheaper by the Dozen 2.She has most recently appeared in According to Greta and Stay Cool.Her first major role was as a star of the 1998 film Casper Meets Wendy, a direct-to-video sequel to Casper: A Spirited Beginning in which she plays the young witch Wendy, who befriends the animated character Casper.The film was released to mostly unenthusiastic reviews.Duff's mother encouraged Hilary to take up acting classes alongside her elder sister which resulted in both girls winning roles in various local theatre productions.

Duff released her third studio album, Dignity, which was certified gold in August 2007 and released two singles, "With Love", her highest charting US single to date and "Stranger".However, the plans failed because Duff's representatives said she was not being paid enough for the proposed series.In the movie, she plays a free-spirited girl who is enrolled in a military school and finds it hard to adjust to its strict and disciplined environment.In the same year, she acted opposite her sister Haylie in American Dreams, while in 2005, she played a classmate and idolizer of the title character of Joan of Arcadia. In the same year, Duff was again nominated for a Razzie Award, for The Perfect Man and Cheaper by the Dozen 2.It was released on her seventeenth birthday (in September 2004) and debuted at #2 in the U. Later that year, the Duff sisters lent their voices to the computer animated comedy Foodfight!

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