Every Best Actor Oscar Movie Winner Of The 21st Century Ranked

11. Sean Penn - Mystic River (2003)

Capote Philip Seymour Hoffman
Warner Bros.

Who should have won: Bill Murray - Lost in Translation.

With his first Oscar win of the century, Sean Penn scored raved reviews for his work in Clint Eastwood's bracing drama Mystic River, and as a performance it couldn't feel further away from his later turn in Milk.

Ferocious, raging, and yet endearingly sorrowful as a criminal who loses his daughter in a senseless act of violence, Penn's performance is one of melodramatic anguish and quiet heartbreak. Perfectly balanced, the actor is a force to be reckoned with, despite his subtle insecurities and grief.

Mystic River's most famous scene - wherein he learns of his daughter's death and is almost hilariously restrained by dozens of cops - gives the impression that Penn's role is all ham, but there's a lot more depth and tenderness here than meets the eye.

Contributor

Aidan Whatman hasn't written a bio just yet, but if they had... it would appear here.