Cover Sean Baker, winner of the Best Picture, Best Directing, Best Film Editing, and Best Original Screenplay for “Anora”, in the press room at the 97th Annual Oscars (Photo by Jeff Kravitz/FilmMagic/Getty)
Sean Baker, winner of the Best Picture, Best Directing, Best Film Editing, and Best Original Screenplay for “Anora”, in the press room at the 97th Annual Oscars (Photo by Jeff Kravitz/FilmMagic/Getty)
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Real surprises are few and far between at the Academy Awards, but sometimes things just don’t go as expected
The Academy Awards is a night where cinematic dreams come true—but for every ecstatic winner, there are just as many crushed hopes. While oddsmakers and industry insiders can usually predict the night’s biggest victors, every now and then, an upset sends shockwaves through Hollywood and ignites a firestorm of reactions online.
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At the 97th Academy Awards, the biggest shocks of the night came courtesy of Anora, an underdog indie film that defied expectations and walked away with a historic trophy haul. Directed by Sean Baker, Anora was initially seen as an arthouse favourite but not a frontrunner in major categories. However, in a stunning turn of events, the film claimed top honours, including Best Picture, which it won over films like Emilia Pérez, The Brutalist and I’m Still Here. The film’s lead actress, Mikey Madison, also delivered one of the night’s most emotional moments as she won Best Actress, besting established stars and cementing her place as one of Hollywood’s rising talents.
In honour of Anora and its shocking Oscar sweep, here’s a look back at the biggest, boldest, and most controversial Oscar upsets of all time.
1. Mikey Madison wins over Demi Moore (2025)
Anora was a slow burner all season long, managing only to get some momentum nearing the Oscars. Madison’s Oscar for Best Actress, winning over sentimental favourite Demi Moore, who would have taken home her first Oscar for her performance in The Substance, and even over the wildcard choice Fernanda Torres for I’m Still Here.
This was supposed to be Demi Moore's year. Not only was this “popcorn actress” getting some much-deserved credit, but she was making a point for mature women everywhere. Some say that her surprise loss to a 25-year-old was the theme of The Substance playing out in real life.
Also read: 6 underrated Demi Moore movies you need to appreciate
2. “Brokeback Mountain” Loses to “Crash” (2006)
This upset was so bad, the Academy had to spend years pretending it didn’t happen.
The smart money was on Brokeback Mountain, a groundbreaking, deeply moving and groundbreaking love story that dominated awards season. But then, the Academy crowned Crash, a preachy, heavy-handed race drama that, in hindsight, aged like room-temperature milk. Even the ceremony’s producer later admitted they “probably got it wrong.”
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3. Glenn Close (again and again and again)
At this point, it’s performance art.
Glenn Close is one of the greatest actresses of all time, and yet she has zero Oscars. The closest she ever got was in 1989 for Dangerous Liaisons, but the Academy gave Best Actress to Jodie Foster for The Accused. Flash forward to 2019, and everyone assumed Glenn was finally getting her due for The Wife (she did, after all, win Best Performance in a Motion Picture – Drama at the Globes). However, Olivia Colman (The Favourite) pulled off one of thsoe last-minute Oscar upsets.
Even Colman was so shocked that she apologised to Close in her acceptance speech.
4. “Saving Private Ryan” gets steamrolled by “Shakespeare in Love” (1999)
Steven Spielberg’s Saving Private Ryan was a technical and emotional masterpiece, but it went home without Best Picture, thanks to a legendary (and now infamous) Oscar campaign by Harvey Weinstein. He turned Shakespeare in Love, a charming but decidedly non-war-epic film, into the frontrunner with aggressive lobbying and some strategic schmoozing.
Did Shakespeare in Love deserve the win? Probably not, and given what we know now about the disgraced producer’s alleged harrassment of Gwyneth Paltrow, it’s now even harder to watch. But it did teach us all a valuable lesson: never underestimate a determined person's ability to rig the game. Spielberg has three Oscars to his name, but this loss is one of the most unforgettable Oscar upsets to this day.
5. Eddie Murphy’s Oscar dreams shattered (2007)
Bad timing killed Eddie Murphy's Best Supporting Actor hopes. Eddie Murphy was the clear favourite to win Best Supporting Actor for Dreamgirls. He had already won the Golden Globe, the BAFTA and the SAG Award. But then, Norbit happened.
Yes, just weeks before the Oscars, Murphy’s critically reviled comedy about a man in a fat suit dropped, and suddenly, Academy voters weren’t so keen on handing him a statue. Alan Arkin (Little Miss Sunshine) ended up taking the prize instead, and Murphy left the ceremony right after losing.
To be fair to the comedy legend, the Academy has handed out Oscars to actors who've done some questionable work simultaneously. Sandra Bullock won her Oscar for The Blind Side and a Razzie for All About Steve in the same year. Eddie Redmayne got a Razzie for Jupiter Ascending a year after he clinched his Oscar for The Theory of Everything.
6. Lauren Bacall loses to Juliette Binoche (1997)
Lauren Bacall had been Hollywood royalty since the 1940s. By 1997, she was considered a lock for Best Supporting Actress for The Mirror Has Two Faces. But then, in a shocker, the award went to Juliette Binoche for The English Patient. Bacall, visibly stunned, did not bother pretending to be happy. The camera caught her giving the kind of side-eye that could curdle milk. She did smile and applaud later, though.
7. Chadwick Boseman’s posthumous loss to Anthony Hopkins (2021)
Everything about the 2021 Oscars suggested that Chadwick Boseman was going to win Best Actor for Ma Rainey’s Black Bottom. The ceremony even restructured its entire running order so that Best Actor was the final award of the night, severely implying an emotional, posthumous win. Then they announced Anthony Hopkins (The Father) as the winner.
Hopkins wasn’t even at the ceremony. Covid-19 was still at its peak and the Academy did not allow the 83-year-old to join via Zoom. Rumour has it that Hopkins was asleep. So the festivities just… ended. No speech. No tribute. Even Hopkins himself was so stunned he later recorded a belated acceptance speech from his living room.
8. Marisa Tomei’s win sparks a conspiracy theory (1993)
Did Marisa Tomei really win? Or did Jack Palance just say the wrong name? Tomei’s surprise win for My Cousin Vinny over established legends like Vanessa Redgrave and Joan Plowright was so shocking that people started a conspiracy theory. Rumours swirled that presenter Jack Palance, who was in his 70s at the time, accidentally read the wrong name and the Academy was too embarrassed to correct it.
The truth? Tomei won fair and square, and the Academy eventually shut down the gossip. But even now, some sceptics still whisper about this Oscar upset.
9. Beyoncé loses Best Original Song (twice)
If Beyoncé can lose, no one is safe. She's had not one but two Oscar upsets.
Beyoncé has been snubbed by the Academy twice in the Best Original Song category. First, in 2019, when “Shallow” (A Star Is Born) beat “All the Stars” (Black Panther). And then, in 2022, when “No Time to Die” (Billie Eilish for James Bond) won over Bey’s “Be Alive” (King Richard). At this point, Beyoncé deserves an honorary Oscar.
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