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5. Brad Pitt

Pitt grew up in Missouri attending Kickapoo High School, where he was a member of the golf, swimming and tennis teams. He also participated in the school’s Key and Forensics clubs, school debates, and in musicals. Sounds like a pretty well-rounded student to us. The Fury actor wore a grey suit and his signature smile to his 1981 high school prom.

awkward celebrity prom photos
Photo: http://www.topinspired.com/

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