Top 10 Biggest Oscar Upsets

Notice how on my Oscar coverage of the acting categories this year, I have discussed a potential upset to occur. That's because I would actually love to see an upset and also because they could actually happen. As evidenced by some of the following upsets in Oscar history, nothing is guaranteed. Here are, in my opinion, the top 10 biggest Oscar upsets in Oscar history.


10: Million Dollar Baby wins Best Picture over The Aviator and Sideways in 2004: It seemed that back in 2004 or technically 2005, The Aviator and Sideways were going neck in neck with The Aviator winning Best Picture at the Globes, BAFTAs, and the Producers Guild, and Sideways winning Best Picture at the Globes and Critics' Choice, as well as Best Cast at the SAG Awards. That is until Barbra Streisand opened the envelope and announced that Million Dollar Baby was the winner.

9. Three 6 Mafia wins Best Original Song in 2005: Three 6 Mafia: Oscar winners. Who knew those two words would be synonymous with Three 6 Mafia. I mean, it's nice to see that the Academy had a slight change of pace and recognized something other than just love songs and all, but still. I'm sure there were plenty of gasps in Hollywood when Queen Latifah announced Three 6 Mafia as the winners.

8. Marisa Tomei wins Best Supporting Actress in 1992: Not just one of the biggest upsets in history, but one of the biggest Oscar myths. The myth is that Jack Palance, who presented the award, was so drunk, he read the wrong name or said it as a joke and the Academy didn't know how to accept it back. But the Academy themselves deny the rumor.

7. Marcia Gay Harden wins Best Supporting Actress over Kate Hudson in 2000: It seemed that Kate Hudson had this one in the bag for a few reasons: She's young, she's Goldie Hawn's daughter and she won the Golden Globe. That is until Nicolas Cage read Marcia Gay Harden's name in the envelope. Notice there is a bit of a trend with this category.

6. Denzel Washington wins Best Actor over Russell Crowe in 2001: Russell Crowe seemed poised to win his second Oscar in a row after sweeping the awards circuit. That is up until Oscar night when Julia Roberts opened the envelope and said, and I quote: "And the Oscar goes to...I love my life..Denzel Washington!"

5. Juliette Binoche wins Best Supporting Actress over Lauren Bacall in 1996: When Lauren Bacall was nominated for her supporting turn in The Mirror Has Two Faces, it was her first nomination and many experts felt that Bacall would benefit from Academy members thinking "It's time" and hand her the coveted statue. That is until Kevin Spacey read Juliette Binoche's name from the envelope. Even he looked pretty shocked. Binoche herself actually said that she didn't prepare a speech because she thought Bacall would win it.

4.  Sean Penn wins Best Actor over Mickey Rourke in 2008: Back in 2008, Mickey Rourke was undergoing a comeback with his performance in The Wrestler and with his comeback narrative, it seemed he would be poised to win the Oscar. I'll admit, even I thought he was going to win, and when Sean Penn's name was called to the stage, I was pretty shocked. That's why I ranked this upset pretty high.

3. Alan Arkin wins Best Supporting Actor over Eddie Murphy in 2006: Eddie Murphy has always been known as a comedian and was winning many awards for his dramatic turn in Dreamgirls. I remember when I watched the ceremony and was certain Murphy would win the Oscar, and he could say "Hercules! Hercules! Hercules!". That is until Rachel Weisz read Alan Arkin's name from the envelope. I quite remember how shocked I was.

2. Adrien Brody wins Best Actor over everyone in 2002: Adrien Brody was a relative unknown when he won for his lead turn in The Pianist, and considering the competition he was up against: previous winners Nicolas Cage, Michael Caine, Daniel Day-Lewis, and Jack Nicholson, he must've been a long shot to win the award. Not only did Brody snag the Best Actor award, but he managed to snag a kiss from presenter Halle Berry. *Note: Similar to this category, Amy Adams is the only Best Actress nominee this year that hasn't won yet. Look out, Cate Blanchett!

1. Crash winning Best Picture over Brokeback Mountain in 2005: When you watch the video of Crash winning Best Picture, the look on presenter Jack Nicholson's face says it all. He even gave an expression that said "Bet you didn't see that coming". I know many of us didn't. It was certainly a very controversial Best Picture win. In fact, some say it is the worst Best Picture winner ever. Regardless, it is still, one of, if not the biggest Oscar upset ever.

Here are a few honorable mentions: Anna Paquin winning Best Supporting Actress in 1993, Shakespeare In Love winning Best Picture over Saving Private Ryan in 1998, James Coburn winning Best Supporting Actor in 1998, The Lives of Others winning Best Foreign Language Film in 2006


So, those are, in my opinion, the biggest Oscar upsets of all time. Those show that each year on Oscar night, nothing, and I mean, NOTHING is guaranteed and on March 2nd, anything could happen. Thanks for reading!