The Academy Awards have long been regarded as the pinnacle of cinematic achievement, celebrating the best in film each year. However, the Oscars are not without controversy, and sometimes, the winners leave audiences and critics alike in shock. Over the years, there have been some truly unforgettable upsets—moments when the expected winner was left empty-handed while an underdog walked away with the golden statue. Here’s a look at five of the biggest upsets in Oscar history.
1. Shakespeare in Love Defeats Saving Private Ryan (1999)
Few Oscar upsets have been as talked about as Shakespeare in Love winning Best Picture over Saving Private Ryan. Steven Spielberg’s war epic was widely considered the frontrunner, lauded for its intense realism and emotional depth. However, the romantic period comedy-drama Shakespeare in Love, bolstered by an aggressive awards campaign by Miramax, managed to secure the top prize. Many believed the win was driven more by industry politics than merit, making it one of the most controversial decisions in Oscar history.
2. Crash Wins Best Picture Over Brokeback Mountain (2006)
Brokeback Mountain, the groundbreaking love story between two cowboys, was heavily favored to win Best Picture in 2006. The film had dominated awards season, winning at the Golden Globes, BAFTAs, and Directors Guild Awards. However, in a shocking twist, the Academy awarded Best Picture to Crash, a racially charged drama that, while critically respected, had not generated nearly the same level of acclaim. Many saw the decision as a safe and conservative choice, snubbing a film that tackled LGBTQ+ themes at a time when Hollywood was still hesitant to embrace such narratives.
3. Marisa Tomei Wins Best Supporting Actress (1993)
Marisa Tomei’s win for My Cousin Vinny remains one of the most infamous upsets in Oscar history. Competing against veteran actresses such as Vanessa Redgrave, Joan Plowright, and Judy Davis, Tomei’s lighthearted performance in a comedy seemed like an unlikely choice for Oscar gold. The upset was so shocking that rumors circulated that presenter Jack Palance had mistakenly read the wrong name. However, the Academy later confirmed Tomei’s win was legitimate, solidifying her place in Oscar lore.
4. Moonlight Wins Best Picture—After La La Land Is Announced (2017)
No Oscar moment has ever been as chaotic as the infamous mix-up during the 2017 Academy Awards. La La Land was first announced as Best Picture, and the entire cast and crew were already giving speeches when it was revealed that Moonlight was the winner. While the mix-up was a mistake, the upset was still monumental—La La Land was the presumed frontrunner. At the same time, Moonlight, a smaller indie drama about identity and self-discovery, defied the odds to claim victory.
5. Adrien Brody Beats Out Daniel Day-Lewis (2003)
In one of the most unexpected Best Actor wins, Adrien Brody won the Oscar for The Pianist over Hollywood heavyweight Daniel Day-Lewis (Gangs of New York). Brody’s performance was praised, but few believed he had a real shot at winning against Day-Lewis, a revered method actor. His shock was evident when he planted a now-famous kiss on presenter Halle Berry.
These Oscar upsets prove that surprises can always happen, no matter how predictable the awards seem.
