The Academy Awards remain the most prestigious film prizes in the world, with millions tuning in every year to watch the ceremony. But with such an important event, controversy and surprise are never far away. Over the decades, some Oscar decisions have left audiences and critics scratching their heads. Here are our top three most unlikely winners in Oscar history.
One of the most unforgettable moments came during the 2017 ceremony, when La La Land was mistakenly announced as Best Picture before the mix-up was corrected live on stage. The actual winner turned out to be Moonlight. While Damien Chazelle’s romantic musical seemed to have “Oscar winner” written all over it, the Academy went in a different direction. Out of its 14 nominations, La La Land still walked away with six trophies, but losing the biggest prize was shocking. Moonlight’s triumph was historic, and its social and cultural relevance may have tipped the scales. As Mahershala Ali, who won Best Supporting Actor for the film, explained: What excited me was that these were people who I grew up seeing. But I’ve never seen the camera pointed at them. And I have seen versions of these people, but the ones that really feel authentic and who are well-rounded and fleshed out. Like sure, you have someone who may deal in some type of criminal element. But he could also be a really good father.
Another infamous upset happened in 1999, when Shakespeare in Love took home Best Picture, beating Steven Spielberg’s Saving Private Ryan. Most expected Spielberg’s World War II drama to dominate, but producer Harvey Weinstein campaigned relentlessly for his film. He pushed his cast into an exhaustive press tour and targeted Academy voters with aggressive lobbying, effectively changing how Oscar campaigning worked. His strategy paid off: Shakespeare in Love collected seven Oscars in total, including Best Actress for Gwyneth Paltrow, who later reflected: To be in a movie of this caliber, it’s really exciting. And there were so many things about it that just were incredibly appealing to me. And it was nice to get to play different people, which is kind of a fun actor thing. But it’s even nicer to be part of a script that is this good.
Finally, our top pick for the most unlikely win has to be Crash over Brokeback Mountain in 2006. Critics and audiences alike widely believed Ang Lee’s groundbreaking love story would take home Best Picture. Even Crash’s own director, Paul Haggis, admitted that he thought Brokeback Mountain was the better film. Yet Crash won, likely due to its ensemble structure and central theme of racism, which resonated with voters and ended on a more hopeful note. Sandra Bullock, who appeared in the film, emphasized the importance of its message: This is an important story to tell. And the timing is perfect because it’s allowed us to get comfortable again, and to feel like we might be safe, and we’re not. We’re not safe from ourselves. We’re not safe from our prejudices or others’ prejudices. It’s rare when you read something that inspires you to leave your home and rectify the situation, and I just wanted to be a part of it.
The Academy Awards will no doubt continue to produce moments of triumph, heartbreak, and controversy. As the next ceremony approaches, we can only wonder what unexpected choices might be waiting.
