5 most shocking Oscar wins ever, ranked

A man holds up an envelope at the 2017 Oscars.
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Usually, you can pretty much predict who is going to win an Academy Award. If you’re a dedicated movie fan, you’ll know who was nominated for a Golden Globe, what film scooped up a lot of Critics Choice Awards, and who took home a SAG Award. By the time Oscar night rolls around, the winners have all but been anointed.

Yet there have been times when not all has happened as predicted. An underdog performer can beat the odds and win or a fan-favorite movie can win over enough voters to take the top prize. In its 96-year history, there have been some surprising victories that have left fans happy or angered. These are the five most shocking wins ever.

Need more Oscar recommendations? Check out how to watch the 2024 Oscars for free, 2024 Oscar predictions, 10 biggest Oscar snubs ever, 10 best Oscar-winning movies ever, 10 most Oscar-nominated movies ever, and 5 great Oscar-winning movies on Amazon Prime Video.

5. Geena Davis wins for The Accidental Tourist (1988)

Geena Davis Wins Best Supporting Actress | 61st Oscars (1989)

1988 was a terrific year for actresses. In the lead category, Jodie Foster won her widely-praised work in The Accused, beating the likes of Glenn Close in Dangerous Liaisons, Meryl Streep in A Cry in the Dark, Melanie Griffith in Working Girl, and Sigourney Weaver in Gorillas in the Mist. The supporting category was just as competitive, with Weaver and co-star Joan Cusack the frontrunners for Working Girl, plus future three-time Oscar winner Frances McDormand (Mississippi Burning) and eventual Catwoman Michelle Pfeiffer (Dangerous Liaisons).

So it was a shock to see Geena Davis win for The Accidental Tourist on Oscar night. While the film had been nominated for Best Picture, Davis had not won a single critics award before the ceremony; heck, she wasn’t even nominated for a Golden Globe, which is usually a reliable indicator of who will win. It’s an OK performance, but it didn’t have the critical or popular support her fellow nominees had during the awards season.

4. Glenn Close loses (again), this time to Olivia Colman in The Favourite (2018)

Olivia Colman wins Best Actress

The World According to Garp. The Big Chill. The Natural. Fatal Attraction. Dangerous Liaisons. Albert Nobbs. Six times Glenn Close has lost the Oscar, but the seventh time looked like it was the charm with The Wife, a middlebrow 2018 drama that received respectable enough notices to push the respected thespian into the Oscar race for Best Actress after a long absence. While she had strong competition from A Star is Born‘s Lady Gaga, it was generally believed that the time finally seemed right to give Close her long overdue Oscar.

It was not meant to be. In an upset, Close lost, but not to Lady G.; both lost to British actress Olivia Colman in the critical hit The Favourite. It was the rare time the Academy actually chose the best performance that year over a sentimental favorite. Colman was terrific and deserved to win for her funny, sad take on the voracious and vindictive Queen Anne. But it was a sad sight to see Close go home empty-handed yet again.

3. Adrien Brody beats Jack Nicholson and Daniel Day-Lewis (2002)

Adrien Brody wins the Academy Award for Best Actor In A Leading Role

2022 saw four legends of the silver screen get beaten by a 29-year-old up-and-coming actor who was then best-known for having his lead role cut to a glorified cameo in 1998’s The Thin Red Line. So how did Adrien Brody, that newcomer in question, beat the likes of Jack Nicholson in About Schmidt, Daniel Day-Lewis in Gangs of New York, Michael Caine in The Quiet American, and Nicolas Cage in Adaptation?

For his work in The Pianist, Brody showcased the holy trinity of Oscar-winning attributes: He lost weight (30 pounds!) for the role; he starred as a real-life person, Polish pianist Władysław Szpilman; and the movie he was in was set during World War II. In addition, he learned to play the piano like Szpilman, broke up with his girlfriend, and gave up his car to immerse himself in the role. Perhaps most importantly, he was great in the film, and the win, while surprising, was also richly deserved.

2. Marisa Tomei wins for My Cousin Vinny and starts an Oscar conspiracy theory (1992)

Marisa Tomei Wins Supporting Actress | 65th Oscars (1993)

There was no way Marisa Tomei was going to win in 1993. Never mind that her brilliant comedic work in My Cousin Vinny was worthy of an award, the prevailing wisdom then (and even now) is that Oscar doesn’t really like comedies. Also, she was up against a quartet of respectable English and Australian actresses, each of whom delivered their own Oscar-worthy performance in roles more designed to appeal to voters than an shaggy comedy starring Joe Pesci as an Eye-talian lawyer defending the Karate Kid on a trumped-up murder charge.

But win she did, and the shock was so great it instantly ignited an Oscar conspiracy theory that persisted for decades. Why? Well, when the previous winner for Best Supporting Actor, Jack Palance, presented the award, some thought the then-74-year-old actor was confused and said the wrong name. How else could you explain Tomei’s improbable win? This conspiracy was somewhat debunked in 2017, when Faye Dunaway incorrectly proclaimed that La La Land had won Best Picture, prompting the Academy’s accounting firm to go onstage and set it right. Speaking of that fateful night…

1. Moonlight wins Best Picture (2016)

"Moonlight" wins Best Picture

Everyone remembers the “big Oscar mistake” when co-presenters Warren Beatty and Faye Dunaway were mistakenly given the wrong envelope and announced that La La Land had won Best Picture. It wasn’t totally outlandish; after all, the Damien Chazelle musical was the frontrunner to win in the category and had already scooped up major awards like Best Director and Best Actress earlier in the ceremony.

But what was overshadowed that night was just improbable and historic Moonlight winning Best Picture actually was both at the time and even today. Indie films without a heartwarming, relatable lead, complete with an all-Black cast and focusing on themes of sexuality, child abuse, and generational trauma, just didn’t win Best Picture. That it did, and that it beat not only its colorful, star-led rival but also more traditional contenders like Lion and Hidden Figures, is surprising enough; that the Academy picked the right movie, one that will stand the test of time, is more shocking than whatever else happened that fateful night.