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She's All That (1999)

Comedy/Romance from Robert Iscove starring Freddie Prinze Jr., Rachael Leigh Cook and Matthew Lillard

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Synopsis

High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.