Guess Who This Kid On The Playground Turned Into!

Before this suave kid in his plaid blazer made his way to Hollywood, he was just hopping on his play set in the backyard, growing up in Charlottesville, Virginia before moving to Point Dume in Malibu, California.

Kicking off his acting career at just 12 years old, he quickly turned into a teen idol and was in a handful of popular movies including "The Outsiders," "About Last Night" and "Square Dance." He also played Sam Seaborn on the show "The West Wing."

Need one more clue? He went to Santa Monica High School with Charlie Sheen.