Ben Affleck and Matt Damon — 1998

Age: 25 and 27

Nominee: Actor in a Leading Role, Good Will Hunting (Matt) Winner: Writing (Screenplay Written Directly for the Screen), Good Will Hunting #Fact: Childhood friends Ben and Matt both brought their moms to the red carpet and had one of the most adorable acceptance speeches to ever exist. Matt would eventually be nominated two more times, and Ben once more, winning Best Picture in 2013 for Argo.