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The Unexpected Oscar Wins Of Year’s Past

Telisa Carter

February 5, 2019

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Every new year brings in a new awards season for the biggest stars in the entertainment industry. From the Golden Globes to the SAG Awards, and of course the Emmys, BAFTAs and the Grammys, there is plenty of opportunity for celebrities and those behind the scenes to be recognized for their work, but there is no bigger night than the Academy Awards. The Oscar is the most coveted statue when it comes to being recognized in Hollywood, and earning one is often the pinnacle of the winner’s career. With lead up awards shows like the Golden Globes and SAG Awards beginning the year, by the time the Oscars roll around, there is already a pretty good idea on who will win, but sometimes upsets are pulled off! Here are the most surprising and shocking Oscar wins of all time:

12. Best Actor – Robert Donat (1940)

The 1940 Academy Awards were stocked full of Hollywood’s most iconic stars, and of course marked the year to celebrate 1939’s Gone With the Wind. The film took home eight awards this year, but Clark Gable didn’t walk away with Best Actor which shocked everyone. While it was assumed that Gable was going to win, there was talk of maybe James Stewart upsetting the assumptions for his work in Mr. Smith Goes to Washington. Incredibly, neither man won and to everyone’s surprise Robert Donat’s name was called for his role in Goodbye, Mr. Chips.

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11. Best Picture – Moonlight (2017)

The 2017 Academy Awards brought one of the biggest mishaps in awards show history when Warren Beatty and Faye Dunaway announced La La Land as the winner of best picture — but they had been handed the wrong envelope. Of course, everyone assumed that La La Land was going to win Best Picture because it won six other Oscars and was named Best Motion Picture – Musical or Comedy at the Golden Globes a month earlier. When it was revealed that there had been a mix-up and Moonlight was the actual winner of Best Picture, everyone was shocked not only by the upset win but the dramatic fashion in which it was announced.

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

Leading up to the 1942 Academy Awards, Citizen Kane was by far the top film of 1941 and has gone on to be considered one of the greatest films of all time, yet it did not walk away with Best Picture. While Citizen Kane wasn’t as celebrated when it was released as it is now, it was still a Best Picture frontrunner, with others betting on The Maltese Fiction. Instead, John Ford’s drama How Green Was My Valley swept through and collected Best Picture along with four other Oscars that year!

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9. Million Dollar Baby (2005)

For most of 2004, Martin Scorsese’s The Aviator was in talks as the best film of the year and many assumed it would sweep the Oscars. Unfortunately for Scorsese and The Aviator, Clint Eastwood’s Million Dollar Baby was released in December and instantly took the hype away from The Aviator. While The Aviator still walked away with five Oscars, it was Million Dollar Baby that scored big in major categories earning four awards including Best Achievement in Directing, Best Supporting Actor, Best Leading Actress and Best Picture of the Year.

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8. Best Director – Roman Polanski (2003)

Director Roman Polanski’s Best Director win in 2003 was a major shock to everyone. Despite 2002’s The Pianist being a great film, it was not expected that the disgraced director, who had not been allowed in the U.S. for decades because of his sexual abuse case, would win. All odds were on either Martin Scorsese for Gangs of New York or Rob Marshall for Chicago before presenter Harrison Ford announced the startling news that Polanski had won. The surprise quickly wore off however, and Polanski was given a standing ovation from many, and Ford accepted the award on his behalf.

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7. Best Picture – Rocky (1977)

With Network, Taxi Driver, Bound for Glory and All the President’s Men up for Best Picture alongside Sylvester Stallone’s Rocky in 1977, it wasn’t expected for the sports drama to take home the big win. Rocky went on to be the ultimate underdog story when it took home the Academy Award for Best Picture. While some still do not agree that Rocky deserved to win Best Picture, the film and franchise’s legacy has only grown and nearly three decades later, Sylvester Stallone won the Golden Globes for Best Supporting Actor as Rocky Balboa in Creed at the 2016 awards.

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6. Best Picture – Chariots of Fire (1982)

Chariots of Fire is all about surprising wins, so it was fitting when the film ran away with the Best Picture award back in 1982. That year’s awards show was notably crowded with heavy hitting films each with their own distinct appeals, yet no one thought the British sports drama Chariots of Fire had a chance against the epic Reds, the heartwarming On Golden Ponds or even the fan-favorite Raiders of the Lost Ark. Even the filmmakers were noticeably in shock when it was announced that their movie Chariots of Fire had secured the win for Best Picture.

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5. Best Director – Kevin Costner (1991)

Martin Scorsese is a celebrated director but he has to take his fair share of hits when it comes to surprising Oscar losses, and one of the biggest was when he was up against none other than actor Kevin Costner in 1990. While Dances With Wolves was a great film, it didn’t have the same impact that Goodfellas did, and when Costner won for Best Director and Dances With Wolves also took home Best Picture, Scorsese instantly became the “best director not to win an Oscar.” Audiences felt that Scorsese was snubbed and when he finally won in 2007 for The Departed many felt it was in response to the backlash.

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4. Best Supporting Actress – Juliette Binoche (1997)

Back in 1996, no one even seemed to question that Lauren Bacall was going to win the Oscar for Best Supporting Actress. After fifty years in Hollywood, Bacall had finally been nominated for her work in The Mirror Has Two Faces, and since the Academy is known to honor those with lengthy careers it was expected Bacall was set for the win. Instead, Juliette Binoche was named the winner for Best Supporting Actress for her work in The English Patient. Binoche was not expecting the win and Bacall did not hide her disappointment. In her autobiography, Bacall noted that she really wanted the Oscar and went on to blame Harvey Weinstein and his aggressive campaigning for The English Patient for her loss.

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3. Best Picture – Shakespeare in Love (1999)

Everyone in the film industry knows to not be too secure in their film for the year, because dark horses often get released in December, just in time to be up for the following year’s Academy Awards. Back in 1998, Steven Spielberg’s Saving Private Ryan debuted in the summer and it was instantly proclaimed as the sure winner for Best Picture. Unfortunately for them, Shakespeare in Love was released in December, and once again Harvey Weinstein began his heavy campaigning for his film. Again, it was Harrison Ford who was presenting and when he announced that Shakespeare in Love had beat Saving Private Ryan for Best Picture, audible gasps from the audience could be heard. The film also pulled off an upset in the Best Supporting Actress category, as Judi Dench won for playing Queen Elizabeth I, despite her lack of screen time. Spielberg was reportedly so upset by the loss he refused to go backstage after the show for press.

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2. Best Supporting Actress – Marisa Tomei (1993)

Few Oscar wins stunned the audience as much as when Marisa Tomei went home with the Oscar for Best Supporting Actress for her role as Monia Lisa in My Cousin Vinny back in 1993. At the time, the newcomer was slotted in alongside actresses such as Judy Davis, Vanessa Redgrave, Joan Plowright, and Miranda Richardson and was a very long shot to win. When her name was announced even Tomei was shocked, and it was so unbelievable, a conspiracy theory quickly followed. Because so many couldn’t believe Tomei actually beat out the others, a theory soon circulated that the presenter, Jack Palance, wasn’t able to read the name on the card so instead just said the last name on the teleprompter from the nominees which was Marisa Tomei. Things got worse when film critic Rex Reed endorsed the theory by stating that Palance was very drunk during the broadcast and said the Academy conducted a “massive cover-up” after the mistake.

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1. Best Picture – Crash (2006)

From snubs back in 1942 to the Oscars So White controversy of 2016, the Academy Awards have seen plenty of drama and a lot of backlash, and it dealt with quite a lot back in 2006. Even in 2005, LGBTQ was not often represented in Hollywood, so when Brokeback Mountain starring Jake Gyllenhaal and Heath Ledger was released that year, it made a lot of waves in the industry. After it cleaned up at the Golden Globes with four wins including Best Picture – Drama, it was thought to get the same honor at the Oscars. When Crash was instead named Best Picture, many were outraged and speculation about homophobia from voters quickly surrounded Crash‘s win. When Jack Nicholson announced the winner, he didn’t hide his surprise and stepped away from the microphone and said “woah.” Even Crash director Paul Haggis, in an interview with Hitflix, admitted he thought the film didn’t deserve to win, praising the artistry of the other nominees, Brokeback Mountain, Capote, Good Night, and Good Luck and Munich. “You shouldn’t ask me what the best film of the year was because I wouldn’t be voting for Crash,” he said.

Telisa Carter

Telisa enjoys learning and writing about all things entertainment in the world of Hollywood. When she isn't catching up on her favorite TV shows, she likes to read, and obsess over all things football.