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After making a cameo appearance in the romantic comedy She's All That, Gellar had the starring role in Simply Irresistible, film that premiered in early 1999.

The film opened to negative reviews and did not do well at the box office.

She admitted in an interview having regrets for her choice to work in the film: " Simply Irresistible was just a bad choice – and for that, it was a great learning experience.

I wasn't ready to make that movie.

I was too young.

The script was not ready.

I knew in my heart before I left to make it that I should back out.