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Hilary 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.

Hilary Duff also served as an uncredited Extra (actor), in writer-director Willard Carroll's ensemble dramedy Playing by Heart in 1998.

Hilary Duff's first major role was as a star of the 1998 film Casper Meets Wendy, a direct-to-video sequel to Casper in which Hilary Duff plays the young witch Wendy the Good Little Witch, who encounters the animated character Casper the Friendly Ghost. The film was released to mostly unenthusiastic reviews