Who was that guy, again?

At the urging of wonderturtle I found myself watching Overboard on TBS today. I found myself transfixed by the fact that the middle boy looked amazingly familiar and yet I couldn't figure out who he was.

What did we do before the The Internet Movie Database ? How else would I know that the girl who played Mia's best friend in The Princess Diaries was the same awkward girl from Welcome to the Dollhouse?

Or that the third son in Overboard was also Josh Baskin's best friend Billy in Big? I feel so much better now that I know who he is.