16 Biggest Oscar Upsets Of The 21st Century

The Rightful Winner: In Bruges

Hey look, it's Sean Penn again. Although, this time, he was absolutely the right person to win Best Actor for his outstanding performance as Harvey Milk.

2009's biggest Oscar upset, however, has nothing to do with how the movie's lines were delivered. It's about the fact that the way they were written robbed one of the best dark comedies ever made of a well-deserved win.

Milk was undoubtedly an important piece of work which chronicled the life and untimely of a hugely important figure in the gay rights movement but peeling the argument back to the central point of screenplay quality, there was a more worthy contender.

Martin McDonagh's script for In Bruges features some of the sharpest, wittiest dialogue ever put to paper. It doubles you over in laughter one moment and within the space of a sentence leaves you crying in the fetal position.

As infinitely quotable as it is bitingly smart, there have been few movies before or since that examined the morality of one's actions from such a unique perspective. His characters are given a level of depth that elevates them beyond their actions and keeps you rooting for them even when you learn more about the sins of their past.

It's very disappointing that the Academy didn't pull the trigger on an In Bruges Oscar win.