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On her role in the movie, she stated during an interview with Entertainment Weekly, "Simply Irresistible was [just] a bad choice—and for that it was a great learning experience. Gellar was cast in the leading role of a mobster's daughter in James Toback's independent drama Harvard Man, but some pointed out the sexual nature of her character, comparing it with that of Kathryn Merteuil in Cruel Intentions; Variety remarked that Gellar was "fun to watch in the adorable, devious bitch mode she test-drove" in her portrayal of Kathryn, and similarly, DVD Talk wrote that Gellar's "self-serving Mafia Maiden echoes her bitchy turn" in the 1999 film.Gellar then appeared as Daphne Blake in the live action–comedy Scooby-Doo, directed by Raja Gosnell and co-starring Freddie Prinze, Jr., Linda Cardellini and Matthew Lillard. reuniting after a two-year disbandment to investigate a popular horror resort in a remote island.
In 2004, Gellar reprised her role as Daphne in Scooby-Doo 2: Monsters Unleashed and portrayed Karen Davis in the horror film The Grudge, both of which grossed more than US0 million worldwide.
The series ran for one season and earned Gellar two Young Artist Award nominations, for Best Young Actress in a New Television Series and for Best Young Actress in an Off-Primetime Series.
She made her debut in the soap opera All My Children in 1993, playing Kendall Hart, the long-lost daughter of character Erica Kane (Susan Lucci).
Gellar was not present in class for most of the time at the school as she had to work in several acting projects simultaneously, recalling that she "had more absences in the first month than you're supposed to have for an entire year.
I was telling them that I had back problems and had to go to the doctor the whole time". La Guardia High School of Music & Art and Performing Arts, but dropped out due to acting obligations; the teachers threatened to fail her because of her constant absence from classes as she was busy going to auditions, despite earning good grades.
She was cast as Helen Shiver, an aspiring beauty actress.