Oscar night is the Super Bowl of Hollywood, a talent contest, and a popularity contest all in one. It’s the only night when red carpet glamour meets nail-biting tension as stars anxiously wait to find out if they’ll hear their names announced. Guesses abound, front-runners are apparent, and yet sometimes the Academy sneaks up and pulls the rug out from under all of us. These shock victories and snubs aren’t only surprising to audience members at the time; they reverberate through the annals of cinema for decades. Below is a decade-by-decade rundown of the most startling Oscar upsets, from recent surprises to golden-age head-scratchers.
10. Mikey Madison Upsets Demi Moore (Anora, 2025)
The ink isn’t even dry on this upset, and it’s already in the books. At the 2025 awards, rookie Mikey Madison shocked the globe by taking Best Actress for Sean Baker’s independent drama Anora over odds-on favorite veteran Demi Moore. Madison, who was clearly shaken, brought things back down to earth by stating that she intended to celebrate by, of all things, cleaning up after her puppies. In her acceptance remarks, she highlighted the worker world depicted in the film, promising to be an ally and advocate. With Anora also winning Best Picture, Madison’s victory seemed like a reminder that occasionally the Academy chooses heart over hype.
9. Olivia Colman Over Glenn Close (The Favourite, 2019)
Awards chatter for months positioned Glenn Close as the lock of the season. Finally, after six losses without a win, her tragic turn in The Wife was her much-awaited crowning glory. In walked Olivia Colman. With her quirky, fragile turn as Queen Anne in The Favourite, she staged the upset of the decade, leaving the viewers agog and Close without an award yet again. Colman’s surprise victory was one of the few bright spots for The Favourite, which lost in nearly all of its other categories. Sometimes, Oscar night really is about the element of surprise.
8. Marisa Tomei Stuns in My Cousin Vinny (1993)
Comedies rarely get Oscar love, which made Marisa Tomei’s Best Supporting Actress win for My Cousin Vinny even more jaw-dropping. She outshone industry heavyweights Vanessa Redgrave and Judy Davis with her side-splitting, show-stopping Mona Lisa Vito performance. The upset was so shocking that it sparked a surreal conspiracy theory—that presenter Jack Palance’s poor reading of the wrong name was actually an error. (For the record: rubbish. Tomei had earned that statuette.) Her victory was evidence that a flawlessly executed comedic turn is every bit as deserving of an award as high drama.
7. Crash Edges Out Brokeback Mountain (2006)
Few of the Oscar selections have been as contentious as this one. Ang Lee’s Brokeback Mountain was a critical favorite and was expected to sweep Best Picture. Instead, the Academy stunned the globe by awarding the award to Paul Haggis’ ensemble piece Crash. Even Haggis himself conceded later on that it wasn’t the greatest film of the year. The reaction was immediate, and for some, this controversy continues to be a reminder of the Academy’s reliance on playing it safe rather than acknowledging real cultural touchstones.
6. The Moonlight/La La Land Blunder (2017)
If you saw this happen live, you’ll never forget it. La La Land’s Warren Beatty and Faye Dunaway also got it wrong in announcing Best Picture, dispatching its cast and crew to the stage for acceptance speeches, only to have producers come out with minutes to tell us Moonlight had been the actual winner. Disorder broke out, headlines burst, and the moment became an instant pop culture icon as “Envelopegate.” Aside from confusion, however, Moonlight’s win was a galvanizing moment for independent, diverse storytelling, and an indication of how the tastes of the Academy were changing.
5. Shakespeare in Love Over Saving Private Ryan (1999)
Steven Spielberg’s Saving Private Ryan was deemed unbeatable: a graphic war epic that the critics and audiences loved. But Miramax’s Harvey Weinstein waged one of the most intense Oscar campaigns in history, bombarding voters with viewings, parties, and unrelenting promotion for Shakespeare in Love. Overwhelming the odds, the romantic comedy-drama won Best Picture, leaving Spielberg’s classic in its dust. The surprise didn’t merely stun the industry but transformed the way Oscar campaigns are conducted, demonstrating that politics and marketing can occasionally trump artistry.
4. Driving Miss Daisy Wins Without a Director Nomination (1990)
When Bruce Beresford’s Driving Miss Daisy won Best Picture, everyone raised an eyebrow not only because it trounced big guns like Dead Poets Society and Born on the Fourth of July, but because Beresford himself hadn’t even been nominated for Best Director. The movie became part of an extremely select group of films that won the highest award without their director receiving accolades. Not until the Argo in 2013 would another movie duplicate the feat. It was one of those puzzling Oscar anomalies that still generate controversy decades later.
3. Art Carney Edges Al Pacino (Harry and Tonto, 1975)
Al Pacino’s work in The Godfather Part II is the stuff of legend, widely regarded as one of the greatest in the history of film. But on Oscar night, the Best Actor prize went instead to Art Carney for his affecting performance in Harry and Tonto, portraying an older widower on the road with his cat. Carney’s performance was sweet and affecting, but nobody thought he could outsuspense Pacino at the height of his powers. The shock confounded critics and viewers alike and has come to be regarded as one of the oddest acting victories in Academy history.
2. How Green Was My Valley Over Citizen Kane (1942)
It’s surprising now, but Orson Welles’ Citizen Kane, frequently cited as the greatest film ever made, lost Best Picture to John Ford’s maudlin drama How Green Was My Valley. Though Ford’s picture was respected during its time, it hasn’t stood the test of time in the same way that Kane has. The shocker has since become a symbol of the Academy’s sometimes fleeting taste, although history has ultimately had the last laugh: Citizen Kane is still a masterwork, whether or not it won an Oscar.
1. The Greatest Show on Earth Outshines High Noon (1953)
Cecil B. DeMille’s circus spectacle was big and gaudy, but few thought it should be Hollywood’s highest honor. But in one of the most notorious Oscar choices ever, it won Best Picture over the gritty, taut western High Noon and the timeless romance The Quiet Man. To this day, pundits cite this upset as evidence that the Academy occasionally honors spectacle over substance. It was a genuine three-ring circus of a choice, and the classic demonstration of how utterly unpredictable Oscar night is.
Oscar night is as much about the upsets as it is about the sure things. These moments, occasionally delightful, occasionally maddening, remind us that the Academy isn’t always predictable, and that’s part of the fun. Whether it’s a treasured underdog coming through or an inexplicable winner that leaves fans scratching their heads, the upsets are what keep folks glued to their screens year after year.