The Great Dictator (1940)

Charlie Chaplin plays both Adenoid Hynkel, dictator of Tomainia, and the Jewish barber mistaken for him. Released in 1940, while the United States was still neutral, it mocks Hitler to his face: the ranting speeches in mock German, the rivalry with Mussolini's stand-in, and the famous dance with a balloon globe that ends when world domination bursts in his hands. The slapstick is gentle and the closing speech drops the joke entirely for a direct plea, which divides viewers. Chaplin later said he could not have made it had he known the full horror of the camps, and that context makes its comedy feel braver rather than naïve.