11. She's All That (1999)

Robert Iscove has directed this film and starring Freddie Prinze Jr., Rachael Leigh Cook, and Paul Walker, this high school rom-com is a classic transformation story. When a popular guy bets that he can turn a shy, artistic girl into the prom queen, neither of them expects to fall in love. Rachael Leigh Cook shines as the quirky and lovable outsider, while Freddie Prinze Jr. brings charm to his role. With a great soundtrack, teen drama, and sweet romance, it remains a nostalgic favorite.
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Edited by Priscillah Mueni