12 Actors Who Won Oscars For Completely The Wrong Role

Won For... Milk And Mystic River

Should Have Won For... Dead Man Walking

Sean Penn absolutely didn't deserve his crowning glory to be in Mystic River, which robbed an Oscar for Best Actor for him, so it's a good thing he then won for the excellent Milk five years later, which was probably pretty galling for Mickey Rourke, given that his The Wrestler performance would probably have won otherwise.

But neither of those wins really deserved the gong as much as his turn in Dead Man Walking, which saw a perfect portrait of contrition, dead-eyed and seemingly cold but with depth to the still waters. There could have been major theatricality in the performance, but instead, Penn is a picture of restraint, dignified and ponderous and he allows the audience space to weigh up the weighty moral issues.

It's just a shame for him that Nic Cage made Leaving Las Vegas the same year.