Biggest Oscar Upsets In History — Moonlight defeating La La Land at the 2017 Oscars remains the most famous Best Picture upset in modern memory. A brief envelope mix-up crowned the wrong film before the correction stunned the theatre.

La La Land entered with fourteen nominations and overwhelming guild momentum. Moonlight's win rewrote the biggest Oscar upsets in history playbook for small indie films beating genre revivals.

Orson Welles's masterpiece lost Best Picture to How Green Was My Valley at the 1942 Oscars. It remains the foundational auteur shock on every biggest Oscar upsets in history list.

Crash defeated Brokeback Mountain for Best Picture in 2006 while Ang Lee still won Best Director. Split-vote theories keep this among the most debated biggest Oscar upsets in history.

Parasite became the first non-English-language Best Picture winner at the 2020 Oscars. Bong Joon Ho's sweep ranks among the biggest Oscar upsets in history for global cinema.