The most shocking Oscar upsets of all time

Brendan Morrow, Staff Writer

March 12, 2023 at 5:07 AM·15 min read

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To predict the Oscars is to be at least a little wrong every year. The history of the Academy Awards is riddled with upset wins that experts never could have seen coming, from the early days of the ceremony to one recent Best Actor surprise that still has our jaws on the floor. As the 2023 Academy Awards approach, these are the most shocking upset wins in the history of the Oscars:

Robert Donat wins Best Actor for 'Goodbye, Mr. Chips'

Would you believe that Gone with the Wind's Clark Gable and Mr. Smith Goes to Washington's Jimmy Stewart competed against each other for Best Actor in 1940, yet neither of them won?

Instead, Robert Donat took home the award for Goodbye, Mr. Chips, a romantic drama that hasn't exactly had the same kind of cultural footprint as the highest-grossing film (adjusted for inflation) of all time, Gone with the Wind. But Donat managed to defeat Gable despite Gone with the Wind itself earning eight Oscars, including Best Picture, while Goodbye, Mr. Chips won no other awards.

'How Green Was My Valley' wins Best Picture

Winning Best Picture isn't always a good thing for a film's legacy. Just take a look at How Green Was My Valley.

If you've ever heard of the John Ford film, there's a good chance it was in the context of it somehow beating Citizen Kane for the Best Picture Oscar in 1942. That's right, the movie now considered by many to be the greatest of all time wasn't even named the greatest film of the year it was released, surely in no small part due to the influence of William Randolph Hearst, the powerful businessman upon whom the character of Charles Foster Kane was based.

In fact, Citizen Kane won just a single Oscar, for its screenplay, offering awards season skeptics a go-to example of how the Academy doesn't always get it right.

'The Greatest Show on Earth' wins Best Picture

With apologies to Steven Spielberg, who has cited the film as an early influence and featured it in The Fabelmans, The Greatest Show on Earth is now viewed as one of the more puzzling Best Picture Oscar winners ever.

Cecil B. DeMille's circus movie won the top prize in 1953, managing to defeat the favorite, the Western High Noon. These days, The Greatest Show on Earth, which holds a "rotten" 49 percent score on Rotten Tomatoes, is widely considered one of the worst Best Picture winners. Were the vote to be held today, Singin' in the Rain would surely win. But believe it or not, at the time, it wasn't even nominated for Best Picture.

Grace Kelly wins Best Actress for 'The Country Girl'

Another early win that still has Oscar historians scratching their heads came in 1955 when Grace Kelly won for The Country Girl — arguably not even her best film of that year, as she was also in Rear Window and Dial M for Murder — and defeated the frontrunner, Judy Garland for A Star Is Born.

Garland seemed to have such strong odds of winning that although she had just given birth, the network sent a camera crew to her so that she could give an acceptance speech from the hospital when she won. "They said, 'Well, you're going to get the Academy Award. We've got to have some extra sets in here so you can thank [host] Bob Hope when you win it,'" Garland later recalled. "...I thought, 'I've got to win it. I'm sure I'm going to win, because they wouldn't go to all that trouble.'"

Instead, Garland's career ended without her having won a single competitive Oscar — though decades later, Renée Zellweger would receive a Best Actress statue in 2020 for playing her.

Art Carney wins Best Actor for 'Harry and Tonto'

Al Pacino delivers arguably one of the greatest performances of all time in one of the best films ever made, The Godfather Part II. Yet neither Pacino nor his fellow nominee, Jack Nicholson in Chinatown, won in 1975.

Art Carney instead took home Best Actor for Harry and Tonto, a film that has been largely forgotten compared to The Godfather Part II and Chinatown. This is despite the fact that Harry and Tonto only had two nominations, while The Godfather Part II had 11 nods and won Best Picture. The Pacino snub was so shocking, his 1993 win for Scent of a Woman is widely seen as the Academy's attempt to make up for that loss and many others, even though few would argue he ultimately won for his best work.

Beatrice Straight wins Best Supporting Actress for 'Network'

If you thought it was odd that Judd Hirsch was nominated for The Fabelmans this year despite only being in the movie for eight minutes, that's nothing compared to what happened in 1977.

Beatrice Straight won Best Supporting Actress that year for her performance in Network, even though she's only in the movie for about five minutes. Straight has just one big scene, yet she still managed to beat Jodie Foster for Taxi Driver. "I'm the dark horse," she acknowledged in her acceptance speech, calling the win "very unexpected." Straight still holds the record for the shortest performance to ever win an Oscar.

'Driving Miss Daisy' wins Best Picture

Sometimes Oscar rules are made to be broken.

Driving Miss Daisy seemed like an unlikely winner in 1990 given it didn't even receive a Best Director nomination. At the time, no film had won Best Picture without a directing nod since 1932. Despite this, Driving Miss Daisy surprisingly won the top prize, defeating Oliver Stone's Born on the Fourth of July, the film that took Best Director.

This another Best Picture winner that's generally regarded as unworthy of the top prize today, though, especially because a film deemed much more resonant and challenging regarding race, Spike Lee's Do the Right Thing, wasn't even nominated. Ironically, history would later repeat itself when Green Book, another film about race and driving, controversially won Best Picture in 2019 despite not being nominated for Best Director — and it defeated another Spike Lee movie, BlacKkKlansman.

Marisa Tomei wins Best Supporting Actress for 'My Cousin Vinny'

You know a win is shocking when it sparks conspiracy theories that it was announced accidentally.

Marisa Tomei came out of nowhere to win Best Supporting Actress in 1993 for My Cousin Vinny. At that point, she was only a few movies into her career, not the major star she is today. Plus, she faced tough competition with nominees like Vanessa Redgrave and Joan Plowright, the latter of whom won at the Golden Globes (where Tomei wasn't even nominated). Besides, My Cousin Vinny is a comedy, a genre that doesn't always earn Oscar love.

Tomei's victory was such a surprise that a false rumor soon spread that presenter Jack Palance read the wrong winner — years before such a mistake would happen for real in 2017.

Anna Paquin wins Best Supporting Actress for 'The Piano'

How's this for a way to start your career: winning an Oscar for your very first film role … at 11 years old.

That happened to Anna Paquin in 1994 when she surprisingly won Best Supporting Actress for The Piano, her first film, and defeated the favorite, Winona Ryder for The Age of Innocence. She's still among the youngest Oscar winners of all time, second only to Tatum O'Neal, who was 10 when she took home her statue for Paper Moon.

Juliette Binoche wins Best Supporting Actress for 'The English Patient'

Best Supporting Actress sure was tough to predict in the 1990s, as another surprise in the category came in 1997.

Lauren Bacall had film credits going back to the 1940s, but it wasn't until 1997 that she was nominated for an Oscar. So it was widely believed that she would win for The Mirror Has Two Faces, which would also partially be a way to recognize her lifetime of great work. She previously won at the Golden Globes and Screen Actors Guild Awards.

But Juliette Binoche shocked pundits by defeating her for The English Patient, and she seemed just as shocked, admitting in her speech that she "thought Lauren was going to get it, and I think she deserves it." The English Patient was a Harvey Weinstein movie, so this is frequently cited as an example of how the disgraced producer's relentless campaign tactics could net surprise wins.

'Shakespeare In Love' wins Best Picture

But when we reflect back on Weinstein's dominance of the Oscars at the height of his powers, the go-to example is Shakespeare In Love winning Best Picture over Saving Private Ryan in 1999.

Steven Spielberg's war epic was considered the frontrunner, coming into the Oscars looking dominant after top wins at the Golden Globes, Producers Guild of America Awards, and Critics' Choice Awards. But Shakespeare in Love was produced by Harvey Weinstein, who ran a famously ruthless campaign that involved aggressive lobbying and even spreading negative buzz about Saving Private Ryan, seeking to convince voters that the film "was all in the first 15 minutes," as marketer Terry Press later recalled to Vanity Fair.

Weinstein's relentless, ultimately successful push for Shakespeare in Love would help shape the way Oscar campaigns are conducted for years to come, for better or worse.

Marcia Gay Harden wins Best Supporting Actress for 'Pollock'

Kate Hudson seemed to be the Best Supporting Actress frontrunner in 2001 for Almost Famous, and she won at the Golden Globes. If anyone was going to beat her, though, Judi Dench appeared to have the best shot for Chocolat after winning at the Screen Actors Guild Awards.

But then … it's Marcia Gay Harden with the steel chair! Harden swept in out of nowhere with a win for Pollock, a film that received just two nominations at that year's ceremony. It was particularly surprising because Harden wasn't even nominated at the Globes or the SAG Awards, making her the only person in history to win after being snubbed by both of those groups.

Adrien Brody wins Best Actor for 'The Pianist'

If you want to score an upset acting win, try being a young actor starring in a movie with a piano-related title.

Years after Anna Paquin's surprise victory for The Piano, Adrien Brody pulled off an upset by winning Best Actor in 2003 for The Pianist, defeating the favorites, Daniel Day-Lewis for Gangs of New York and Jack Nicholson for About Schmidt. Day-Lewis had already won at the British Academy Film Awards and the Screen Actors Guild Awards, and he tied with Nicholson at the Critics' Choice Awards. Nicholson won at the Golden Globes, so he seemed like the only person who could defeat Day-Lewis.

Instead, Brody swept in to beat them both and become the youngest person to ever win Best Actor at age 29 — and he was so overwhelmed, he famously kissed presenter Halle Berry on stage.

'Crash' wins Best Picture

One of the most shocking Best Picture winners of all time is still among the most controversial.

Brokeback Mountain was considered the Best Picture frontrunner going into the 2006 Oscars, having racked up eight nominations, the most of any film. It also already won at the Golden Globes (where Crash wasn't even nominated for Best Picture), the Critics' Choice Awards, the Producers Guild of America Awards, and the British Academy Film Awards, and on the night of the Oscars itself, Brokeback's Ang Lee also won Best Director.

But Crash came out of nowhere for the win — presenter Jack Nicholson mouthed "whoa" after reading it — quickly sparking accusations that homophobia in the Academy prevented voters from getting behind the acclaimed gay romance. The studio's strategy of sending a DVD of Crash to every single member of SAG also may help explain it, as the acting branch is the Academy's largest. Either way, the upset has largely come to define Crash's legacy, and it's still cited by critics as among the least deserving Best Picture winners.

Alan Arkin wins Best Supporting Actor for 'Little Miss Sunshine'

Can a movie be so bad that it derails an actor's campaign for a totally different film?

That was the theory behind Eddie Murphy's shock loss for Dreamgirls in 2007. The comedian was considered the frontrunner that year, having already won at the Golden Globes, SAG Awards, and Critics' Choice Awards. But in the end, he surprisingly lost the Oscar to Alan Arkin for Little Miss Sunshine.

So what happened? Well, just a few weeks before the Oscars, Murphy starred in the critically reviled comedy Norbit, leading to a theory that the movie was so bad, it swayed Academy members away from voting for him for Dreamgirls. We'll never know if that was truly the case, but Murphy reportedly stormed out of the Oscars after his loss. To this day, he has still never been nominated a second time.

'Moonlight' wins Best Picture

La La Land being incorrectly announced as the Best Picture winner in 2017 was such a shock, it's easy to overlook how much of a surprise Moonlight winning would have been even without the gaffe. Damien Chazelle's musical was the overwhelming Best Picture favorite, having won at the Golden Globes, Critics' Choice Awards, the Producers Guild of America Awards, and the BAFTAs, and it tied the record for most Oscar nominations of all time — and that's not to mention that, as a movie that paid tribute to Hollywood, it had Best Picture winner written all over it.

Moonlight, meanwhile, was a far more intimate drama about a gay Black man that was the critical favorite, but seemed too small and quiet to go all the way at the Oscars. Besides, its only major precursor win was a Golden Globe for Best Drama, a category in which La La Land didn't compete. Host Jimmy Kimmel even had a joke in his monologue suggesting no one in the Academy actually watched Moonlight.

But the shock Best Picture victory signaled the birth of a new, more modern Academy open to expanding its horizons beyond what we traditionally view as Oscar fare, and after Brokeback Mountain's loss a decade earlier, the Academy's embrace of a story about a gay man was particularly meaningful.

Olivia Colman wins Best Actress for 'The Favourite'

Some Oscar campaigns are dominated by the narrative that one performer is overdue for a win, as was the case with Glenn Close in 2019. At that point, Close was on her whopping seventh Oscar nomination without a single victory, so wasn't it time she finally be recognized?

Close was sweeping the season that year for her performance in The Wife, winning at the Golden Globes, SAG Awards, and Critics' Choice Awards (in a tie with Lady Gaga). So pundits were stunned that the Academy ignored her yet again by giving the award to Olivia Colman for The Favourite, whose only major win before the Oscars was at the BAFTAs. She was just as stunned, delivering one of the most hilariously overwhelmed Oscar speeches of all time and even telling Close on stage, "This is not how I wanted it to be."

Four years later, Close has still never won an Oscar, making her the most nominated actress in history without a win.

'Parasite' wins Best Picture

So much was working against Parasite. For one, prior to the 2020 Oscars, no non-English language film had ever won Best Picture, and the thinking was it would be difficult to do so because there already exists the Best International Feature Film category. Plus, a movie traditionally needs at least one acting nomination to win Best Picture, and no member of Parasite's cast was nominated.

Besides, the World War I film 1917 was on a roll, having racked up wins at the Golden Globe Awards, Producers Guild of America Awards, and British Academy Film Awards. But Parasite was such a phenomenon that it overcame the odds and made history, likely in large part due to support in the actors' branch, as the film won the top prize at the SAG Awards.

Years after Moonlight, a non-English language film winning continued to prove the Academy is now more open to rewarding different types of films that may never have had a chance before — something that continues to be the case in 2023, in which the frontrunner is a sci-fi movie that involves hot dog fingers and butt plugs.

Anthony Hopkins wins Best Actor for 'The Father'

One of the biggest locks going into the 2021 Oscars appeared to be that Chadwick Boseman would win Best Actor. He tragically died from cancer the year before and was sweeping the season for his posthumous performance in Ma Rainey's Black Bottom. Sure, Anthony Hopkins beat him at the BAFTAs for The Father. But that seemed more like a case of Brits having a bias toward a Welsh actor who has literally been knighted by the queen.

Few seriously doubted Boseman would lose at the Oscars — especially not the telecast's producers. In what turned out to be a disastrous move, they rearranged the show to announce Best Actor as the final category, after Best Picture. It was highly unusual, and the hope was to end the night on a tear-jerker with Boseman's widow accepting his award. But it massively backfired after Hopkins won instead … and he wasn't there to accept, nor did he Zoom in, as he wasn't even awake at the time.

At best, it was a bizarrely anticlimactic ending to the Oscars, and at worst, it was a cynical ploy to manufacture an emotional TV moment from a man's death that was borderline offensive. But at least it proved one thing once and for all: the producers truly don't know the winners beforehand.

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