Barry Fitzgerald was nominated in both categories for his performance in Going My Way in 1944 (current rules prevent this.) He won Best Supporting Actor, losing the Best Actor Award to his costar Bing Crosby. The Oscars weren't the only awards group to confuse his status, as he won Best Actor from the New York Film Critics and Best Supporting Actor from the Golden Globes (although to be fair, the New York critics didn't start awarding a Best Supporting Actor prize until 1969). No other performer has won the Oscar and New York Film Critics award for the same performance in different categories although Valerie Perrine came close in 1974 for Lenny, winning the critics' award for Best Supporting Actress and an Oscar nomination for Best Actress.

Due to the wartime metal shortage during World War II, Fitzgerald (along with all the other Oscar winners of the WWII era) was given a plaster Oscar. He accidentally decapitated it with a golf ball while practicing putting in his living room. His studio paid for a replacement, and he was given a gold Oscar after the war.