8. Ryan Malgarini as Harry Coleman, Freaky Friday (2003)
Anna Coleman's (Lindsay Lohan) younger brother Harry is your basic mischievous brother in a teen drama: He and his friends are weirdly fascinated by his big sister's room, her diary, and he even...dances around in her bra. All because he looks up to her and this is the only way he knows how to get her attention. Understandable, but prancing around in the undergarments takes it a step too far, kid.