16 Biggest Oscar Upsets Of The 21st Century

13. Best Actor - Sean Penn, Mystic River

Mystic River Oscar 2004
Warner Bros. Pictures

The Rightful Winner: Bill Murray, Lost In Translation

Sean Penn, respected performer and world-renowned anger fountain, is the type of actor that the Oscars were created for. He puts so much manic energy into his work that sometimes it veers into the melodramatic but for the most part, as is the case with Mystic River, Penn will reliably deliver the goods.

Mystic River itself is a gruelling film that tackles themes ranging from child molestation to murder and features a stellar cast including Tim Robbins and Laurence Fishbourne who all turn in strong performances. The issue isn't that Sean Penn didn't deserve an Oscar for the movie, it's just that the man he was up against definitely should have won.

Lost In Translation whisper
Momentum Pictures

It's questionable whether this can be classified as an upset or just more of a missed opportunity but because there's not a person alive that doesn't love Bill Murray, let's day it's the former.

Lost In Translation is a bittersweet masterpiece which coaxed a career-defining performance out of Murray who displayed a level of vulnerability and sadness that his delightfully snarky persona usually skates across. It's a modern classic that redefined what a romantic comedy could be and cinema-goers should be eternally grateful.

Bill Murray has only ever been nominated for one Oscar. The fact that he did not receive it will go down as one of the darkest days in awards history.

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Contributor

A pop culture mad writer from the North East who loves films, television and debating them with whoever will listen. Follow me on Twitter @Johno_Patterson