16 Most Surprising Academy Award Wins Of All Time

Ever since the first Academy Awards back on May 16, 1929, there have been many surprises over the years. Often times, the big upsets come up in a select few categories. Best Picture is awarded to the film of the year according to the Academy. But over the course of the 89 Best Picture awards that have been handed out, a handful of those were total shockers. So much so, that even the winners were totally blown away when their names were called out.
It isn’t just the Best Picture category that can be a shocker either. The winners of Best Actor, Actress and supporting titles can provide some Academy Award season scandals as well.

16. Marcia Gay Harden – Best Supporting Actress (2000)

Movie: Pollock

In this movie based on the real life of Jackson Pollock, Marcia played the wife of the abstract artist, Lee Krasner. She wasn’t even nominated for the Golden Globes, SAG Awards, or BAFTAs that year. Which is why jaws dropped when she still won the Oscar. Marcia managed to beat out some top contenders including Kate Hudson for Almost Famous, Judi Dench for Chocolat, Julie Walters for Billy Elliot , and Frances Macdonald Almost Famous. Is it just me or did ANY of those others seem more likely to win than Marcia was? Either way, congrats to her!

15. Anna Paquin – Best Supporting Actress (1993)

Movie: The Piano

Despite only being 11 years old, Anna Paquin snagged the Academy Award that year. She beat out women much older than her, like Emma Thompson for In the Name of the Father, Winona Ryder for The Age of Innocence, Rosie Perez for Fearless, and Holly Hunter for The Firm. In The Piano, Anna played the daughter of a mute woman in the 1850s that is sent to New Zealand with only her young daughter and prized piano to be sold into marriage. She’d had practically no acting experience before filming the 1993 movie. She still holds the record for the second-youngest actress to win this award. Impressive!

14. The King’s Speech –  Best Picture (2011)

The King’s Speech only won one Golden Golden, but then did very well at the BAFTAs. It won seven awards at the BAFTAs and four Academy Awards. But everyone was still surprised that is managed to win the Oscar for Best Picture. 2011 was a pretty competitive year and the film was up against nine other films with great reviews from critics and fans alike. The King’s Speech beat 127 Hours, Black Swan, The Fighter, The Social Network, and more.

13. Grace Kelly –  Best Actress (1955)

Movie: The Country Girl

The big upset here was that Grace Kelly beat Judy Garland in the Best Actress category that year. Everyone thought Judy would win for A Star Is Born, yet was “snubbed” by Grace. Judy never won an Academy Award for Best Actress in her lifetime and at that point in time, everyone had been rooting for her. She only received a Juvenile Award in 1940 after the success of The Wizard of Oz. At the time, Grace won the award for The Country Girl which puzzled critics as she’d starred in two Alfred Hitchcock films that year that were much more interesting.

12. Moonlight – Best Picture (2017)

No one is suggesting that Moonlight shouldn’t have won this Academy Award. In fact, the film topped numerous “best movies of 2016” lists from critics and was, easily, the best movie of 2016. What IS surprising, though, is that it is the second lowest-grossing movie to win the Best Picture award at the Oscars (after The Hurt Locker). Also, there was pretty much a frenzy over how good La La Land was. In fact, the Ryan Gosling and Emma Stone movie was initially announced as the winner and the mistake wasn’t realized until the cast of La La Land was already on stage, accepting the award. Safe to say, this was the wildest ending to an Oscar show in years.

11. Marisa Tomei – Best Supporting Actress (1992)

Movie: My Cousin Vinny

Joe Pesci, Fred Gwynne, and Marisa Tomei were all praised for their work in My Cousin Vinny. In the movie, two New Yorkers are falsely charged with a murder they didn’t commit. Their cousin Vinny, a lawyer fresh out of school, has to defend them. Marisa Tomei’s Brooklyn-born Mona Lisa Vito was one of the best characters in the film. But Marisa winning the Oscar for the role surprised everyone at the time. So much so, some have concocted a conspiracy theory that she didn’t win. The theorists think that it was a mistake and they just let her keep the award to cover it up. They didn’t do that for La La Land though, so it seems unlikely.

10. Crash – Best Picture (2006)

The 2005 film dealt with racial and social tensions in Los Angeles and, in a lot of ways, it was a film before its time. Crash took a different stance on racism, showing victims of racism being prejudiced themselves in other contexts. The film won three Oscars (Best Picture, Best Sound Editing, and Best Original Screenplay). The Best Picture win, however, was the huge upset of the night at the 2006 Academy Awards. Many thought Brokeback Mountain would win, based on its box office and critical success. In fact, people have suggested Brokeback Mountain didn’t win due to homophobic voters in the Academy. HMM…

9. Juliette Binoche – Best Supporting Actress (1997)

Movie: The English Patient

Juliette is another case where many thought that another was more deserving of the title leading to major upset after the Oscar ceremony. Lauren Bacall had yet to win an Academy Award in her illustrious career and it seemed like a sure thing for her work in The Mirror Has Two Faces. But Juliette’s work in The English Patient overshadowed that. The movie follows the love story between a badly burned man and the nurse who cares for him toward the end of WWII. Lauren claims that the constant marketing and lobbying for The English Patient is why she didn’t win.

8. Art Carney – Best Actor (1974)

Movie: Harry and Tonto

Much like the surprise when a very young actor or actress wins, the same surprise can happen when an older actor wins for apparently *no reason*. This 1974 movie is about a man in this seventies that is evicted from his New York apartment so the owners can tear the building down. After trying to stay with his son doesn’t pan out, he decides to travel the country with his cat. It is understandable that given the film’s plot, people were surprised by the win. He beat Al Pacino for his work in The Godfather: Part II and Jack Nicholson for his work in Chinatown. So, yeah… shocking.

7. Adrien Brody – Best Actor (2003)

Movie: The Pianist

Sometimes, the biggest Oscars surprise isn’t for those watching, but those who are participating. Adrien Brody was so shocked by his win, he was blown away when walking on stage. He even passionately kissed the award presenter, Halle Berry! They were not dating at the time and the kiss was not planned. In fact, Halle Berry recently made it clear that it was not something she expected. The win shouldn’t have come as too much of a surprise, as the film was nominated for seven Oscars and won three of those. The Pianist is a World War II memoir by the Polish-Jewish pianist and composer Władysław Szpilman.

6. Rocky – Best Picture (1977)

Rocky was a pretty big upset at the 1977 Oscars because Sylvester Stallone had been virtually unknown prior to the film. He wrote Rocky in three and a half days, after watching the championship match between Muhammad Ali and Chuck Wepner. The movie only had a $1 million budget. At first, producers didn’t even want Sylvester in the film, but he convinced them to let him star in it. The movie beat All The President’s Men and Taxi Driver for Best Picture and people were, well, shook over it.

5. Three 6 Mafia – Best Original Song (2006)

Movie: Hustle & Flow

Yes, you read that right. The rap group Three 6 Mafia has an Academy Award. They were the first rap group to win an Oscar, too. Before they were Cookie and Lucious Lyon on Empire, Taraji P. Henson and Terrence Howard starred in Hustle & Flow. The film follows a pimp living in Tennessee that suffers from a mid-life crisis. With the help of his friends, he tries to become a successful emcee. Three 6 Mafia won for their original song “It’s Hard Out Here For a Pimp.” Only three songs were nominated and this song beat the theme of Crash and Transamerica.

4. Shakespeare in Love – Best Picture (1999)

Everyone thought that Saving Private Ryan would win at the 1999 Oscars. Steven Spielberg won Best Director, so it had seemed that Saving Private Ryan would be a shoe-in. But Harvey Weinstein (yup, that same one) had campaigned hard for Shakespeare in Love and the film came out on top. Starring Joseph Fiennes and Gwyneth Paltrow, the film is set in the 1590s where a young William Shakespeare is out of ideas. He meets a woman who inspires him to write one of his most famous plays, Romeo and Juliet.

3. Kevin Costner – Best Director (1991)

Movie: Dances With Wolves

Before he won the same award for The Departed, there was a huge narrative that Martin Scorsese was the “best director to never win an Oscar” in Hollywood. Back in 1991, it seemed like Martin would win for Goodfellas and break that reputation, though. It was almost a no-brainer. But Kevin Costner swooped in to beat veteran Martin Scorsese with the film he directed, produced, and starred in, Dances With Wolves. What was most upsetting was that this film was Kevin’s directorial debut.

2. Forrest Gump – Best Picture (1995)

At the time, this win felt very unprompted for many, but Forrest Gump is still highly regarded to this very day. The film was very popular at the time of the awards season. And can you really deny the charm that surrounds Tom Hanks? Tom won for Best Actor that night as well, earning him his second Oscar. Even so, it was still confusing for some that this movie won because it beat out the cult classic, Pulp Fiction, and the positively-reviewed, The Shawshank Redemption.

1. How Green Was My Valley – Best Picture (1942)

Throwing it way back, How Green Was My Valley winning at the 1942 Oscars caused quite a stir. At the time of the film’s release, there was a bit of a rivalry with Citizen Kane (which is now regarded as one of the best films of all time). But instead, this film won big at the Academy Awards. Citizen Kane‘s main character, Charles Foster Kane was based on William Randolph Hearst, and that might have hurt their chances with the Academy. How Green Was My Valley was highly regarded at the time, being nominated for ten Academy Awards. But to this day, not many have heard of the winning film, though they have heard of Citizen Kane.

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