1942 – Citizen Kane
It’s surprising to know that “Citizen Kane” a film that constantly lands atop greatest films list, lost the Oscar to “How Green Was My Valley”. “Citizen Kane” was directed, produced, co-written, and starred Orson Welles who is said to have based the film off the life of William Randolph Hearst, the newspaper magnate. It is theorized that due to Hearst’s extreme distaste for this film, he influenced the Academy and that is why it didn’t win the Best Picture Oscar.