13 Biggest Oscar Upsets

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The Academy Awards are Hollywood's annual salute to its finest films that were presented the year prior. Sometimes though, things don't quite go as planned. 

Upsets are notorious at the big event. Like, who would have thought that one of the best films of all time, Citizen Kane, would not be a Best Picture winner? Yeah, that! 

And Martin Scorsese seems to have been upset so many times, we've lost count. 

Click through and discover our 13 biggest Oscar upsets of all time!

1. Good Will Hunting Beats As Good As It Gets, Boogie Nights

Good Will Hunting Beats As Good As It Gets, Boogie Nights
The Good Will Hunting screenplay is top notch, but Oscar-winning good? The Academy felt so as it beat Paul Thomas Anderson’s impressive Boogie Nights and James L. Brooks' fantastic As Good As It Gets.

2. Crash Upsets Brokeback Mountain

Crash Upsets Brokeback Mountain
Brokeback Mountain had everything going for it. The Ang Lee romance had won the hearts and minds of everyone who saw it and it was sweeping the guild awards and just about every critic award up until the big Oscar night. When Crash was revealed as Best Picture, we’ve never heard such a gasp of shock in the Oscar audience in our entire life.

3. Marisa Tomei Beats Legends

Marisa Tomei Beats Legends
Judy Davis, Vanessa Redgrave and Miranda Richardson were all thought to have a bigger chance at winning the Oscar the year they shared a nomination with Marisa Tomei for My Cousin Vinny. Think again, Tomei won and everyone was shocked. Like, everyone as in to this day people think presenter Jack Palance read the wrong name.

4. Shakespeare in Love Beats Saving Private Ryan

Shakespeare in Love Beats Saving Private Ryan
And the era of Harvey Weinstein making the Oscar a political race was officially on. Weinstein famously spent millions of dollars to get people to consider his little romantic period piece for Best Picture and a slew of other awards. Meanwhile, Saving Private Ryan was thought to be a lock for Best Picture. It didn’t work out that way as Harvey’s influence proved large as Shakespeare in Love shocked the world and, more importantly, upset Steven Spielberg’s beloved war epic that starred a national treasure in Tom Hanks.

5. Gwyneth Paltrow Beats Cate Blanchett

Gwyneth Paltrow Beats Cate Blanchett
Speaking of Shakespeare in Love, Gwyneth Paltrow scored because of Weinstein’s pushing his flick. I mean, Cate Blanchett played Queen Elizabeth and shocked the world with her powerful performance. Paltrow was good in Shakespeare in Love, but not even close to Blanchett as a royal good. Score another that year for Weinstein. How powerful was Weinstein's schmoozing? Even Judi Dench won that year for Best Supporting Actress and she was in the movie for only 90 seconds!

6. Adrien Brody Beats Nicholas Cage, Jack Nicholson and Daniel Day Lewis

Adrien Brody Beats Nicholas Cage, Jack Nicholson and Daniel Day Lewis
Oh, and Michael Caine too probably thought he’d win before Adrien Brody did. Those are some pretty huge names to win over. Even though The Pianist was a tour de force for Brody, no one thought he would actually win.

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