The Biggest Academy Award Shockers of All Time
No one saw these coming.
One of the greatest things about the Oscars is the element of surprise. It’s why we throw parties and run betting pools and debate the results for weeks on end. But, even so, every blue moon, there’s a win so unexpected—so surprising that even a night dedicated to surprise couldn’t foresee it—that the country’s collective jaw is left on the floor.
So, to that end, we rounded up all of the most shocking, astonishing, totally out-of-left-field Oscar wins in history. Take a look—and, while you’re at it, maybe reconsider the predictions you have on your roster this year. After all, you never know what could happen.
When Crash beat Brokeback Mountain for Best Picture (2006)
In 2006, Brokeback Mountain did more than make audience members sob in a dark theater full of other heartbroken strangers. It was one of the first critically acclaimed box office hits to explicitly depict a romantic relationship between two men. Every actor in the film gave the performance of their career (at the time), and the entire industry assumed it would easily walk home with the Oscar for Best Picture.
So, when Crash—an underwhelming film that tried to address racism but lacked nuance and insight—took home the award, people were…confused. Even the director of the film, Paul Haggis, didn’t quite understand how he had earned Hollywood’s most prestigious accolade. During an interview with Hitfix in 2015, Haggis commented on the surprise win, saying, “Was it the best film of the year? I don’t think so.” We applaud his honesty.
When Marisa Tomei won Best Supporting Actress (1993)
Sometimes Oscar results are so far out of left field that audiences refuse to believe them. That was the case in 1993, when Marisa Tomei won Best Supporting Actress for her role in My Cousin Vinny. People felt as though both the film and Tomei’s performance were forgettable, and rumors sparked that her name had been read by mistake. This conspiracy has never been confirmed, but the internet refuses to let it go to this day.
When Citizen Kane Didn’t Win Best Picture (1942)
Citizen Kane is regarded by many film historians as the best film of all time. However, back in 1942, the Academy apparently did not agree. Orson Welles’ masterpiece was nominated for Best Picture, but ultimately lost to John Ford’s How Green Was My Valley.
The film wasn’t entirely snubbed, though; Citizen Kane did win Best Original Screenplay that year, and it lives on as the best movie ever in the hearts of movie lovers (and on the pages of film professor syllabi).
When Bob Fosse won Best Director for Cabaret (1973)
Bob Fosse’s astonishing Oscar win has become more and more astonishing over time, as his directorial effort, Cabaret, has failed to remain relevant. His top competition, however, sure has: Francis Ford Coppola, who directed The Godfather, a film of epic proportions that basically every man over 35 can quote in its entirety. Alas, Fosse took the award. (No word on if he left the cannoli.)
When Three 6 Mafia Beat Dolly Parton (2006)
It was completely unexpected for Three 6 Mafia to win an Oscar for their Hustle & Flow theme song “It’s Hard Out Here for a Pimp.” It was also totally refreshing and exciting. The Academy Awards have taken some heat for being overly white-centric, so giving the Oscar to group of black rappers over a white country singer (Dolly Parton was nominated for her song “Travelin’ Thru,” from Transamerica) who was expected to win big. Parton, for her part, took the loss in stride, and congratulated Three 6 Mafia in a public letter. Sometimes surprises are sweet.
When an 11-year-old won Best Supporting Actress (1994)
Most 11-year-olds aren’t able to stay up late enough to watch the Oscars, let alone make history at the event. But that’s exactly what Anna Paquin did, when she became the second-youngest person ever, by winning Best Supporting Actress for her role in The Piano. That feat alone is impressive, but what made it even more so was the the fact that she was up against some seriously stiff competition: Rosie Perez, Winona Ryder, Emma Thompson, and Holly Hunter.
When Shakespeare in Love unexpectedly stole the show (1999)
When Oscar season rolled around in 1999, everyone was expecting Saving Private Ryan to be the big winner of the night. With a Steven Spielberg-helmed, Tom Hanks-led war movie on the ballot, people figured the show was said and done. Little did they know, the night would take a major turn, when announcers began dishing out awards to Shakespeare in Love left and right. The film won a total of eight Oscars that night, including Best Picture, Best Actress (Gwyneth Paltrow), and Best Original Screenplay.
When Rocky won Best Picture (1977)
Because of this very moment, Rocky has been cemented in culture as the the quintessential underdog film. Nobody expected it to win Best Picture, especially going up against instant classics like Taxi Driver and All the President’s Men. But the inspirational film struck a chord with audiences, so the win felts like a victory for both the creators and fans. If Rocky itself wasn’t a solid case that you can win fights with the odds stacked against you, this Oscar moment most certainly was.
When Grace Kelly won an Oscar for her role in The Country Girl (1955)
Grace Kelly winning an Oscar in 1955 wasn’t surprising by any means. It was the same year that she had given two unforgettable performances in two unforgettable Alfred Hitchcock films: Rear Window and Dial M for Murder. But, oddly enough, Kelly won Best Actress for her, um, less iconic role in The Country Girl. The win feels even more perplexing when you consider the fact that it came the same year that Judy Garland had finally been nominated. (Pro tip: don’t bring this one up to diehard Garland fans unless you have a few hours to spare.)
When Leonardo DiCaprio didn’t win, and didn’t win, and didn’t win, and didn’t win, and didn’t win (1994–2016)
In 1994, Leonardo DiCaprio was nominated for Best Supporting Actor for his role in What’s Eating Gilbert Grape. In 2005, he was nominated for Best Actor for The Aviator. In 2007, he was again nominated for Best Actor, for Blood Diamond—and again, in 2014, for The Wolf of Wall Street (which he also nabbed a Best Picture nomination for, since he was a producer on the film). He didn’t win a single award.
Of course, it’s an honor just to be nominated. But, at a certain point, it’s just insulting. Luckily, he broke the bad luck streak in 2016, by picking up a Best Oscar win for his role in The Revenant.
When Adrien Brody won Best Actor (2003)
People weren’t upset about Adrien Brody’s unlikely Oscar win, but they were pleasantly surprised. His performance in The Pianist was generally applauded, but Brody was up against Hollywood heavyweights like Michael Caine, Jack Nicholson, and Daniel Day-Lewis, making his chances to bring home the prize slim to none. He beat all odds when he not only won the award but became the youngest man to ever receive the Oscar for Best Actor, a record he still holds to this day.
When Dances With Wolves beat Goodfellas (1991)
If you’d had to guess who won Best Director in 1991, you’d probably guess that that Martin Scorsese won Best Director for his work in Goodfellas. You’d have guessed wrong, because Scorsese shockingly lost to Kevin Costner, who took the Oscar for Dancing With Wolves in one of the biggest Academy Award upsets of all time.
When Shawshank Redemption lost (1995)
Stephen King’s unforgettable film, starring Tim Robbins and Morgan Freeman, was expected to take all of the big wins of the night. It was nominated for a whopping seven Oscars, and took home a bleak zero. Most upsetting, it lost Best Picture to Forrest Gump. Of course, now, Forrest Gump is a beloved classic. But at the time, its win felt like a complete robbery.
When Chariots of Fire won Best Picture (1981)
Even the filmmakers of this Olympic tale were astounded by its shocking win. There were plenty of worthy Oscar contenders in 1981, including Warren Beatty’s Reds and Mark Rydell’s On Golden Pond. Many were surprised that Chariots of Fire was even nominated, and when its name was called to the Oscar stage, the cast and crew looked around at one another in ecstatic awe. Talk about a gold medal.
That Moonlight vs. La La Land mixup (2017)
It’s perhaps the greatest blunder in Oscar history. (Indeed, the only similar event dates all the way back to 1933, when Frank Capra erroneously walked up to the podium to accept an award that was meant for Frank Lloyd.) But the final category of the 89th Academy Awards sent the entire night into a tailspin. Here’s what happened.
Both La La Land and Moonlight—two commercially successful critical darlings—were nominated for Best Picture. Warren Beatty and Faye Dunaway were presenting the award for the category. But before they went on stage, Beatty was handed the incorrect envelope, and was noticeably confused when he pulled out a card that read “Emma Stone, La La Land.” In retrospect, it was clearly meant for the Best Actress category—which Emma Stone did indeed win for—but, in a moment of confusion, Dunaway declared La La Land as the winner.
Turns out, La La Land wasn’t the actual winner. In the middle of accepting the award, Jordan Horowitz, a La La Land producer, told the audience, “There’s been a mistake. Moonlight, you guys won Best Picture,” and held up the correct card as proof. “This is not a joke.” It sure wasn’t. Oops! And for more blunders from the Academy, check out the 15 Best Picture Oscar Winners Nobody Likes Anymore.
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