In 1940, Paramount released "The Three Stooges" short "You Nazty Spy!". At that point in time, the U.S. had not yet entered what would become World War II, and the pro-Hitler German American "Bund" was strong after its largest rally the year before in New York City.
In the short, the Stooges portray three simpletons recruited to lead a dictatorship in "Moronika", with Moe as the Hitler character, Curly as the Goring character, and Larry as the Goebbels character. Their flag was a pair of twisted snakes resembling a swastika, their slogan was "Moronika for Morons" (like Hitler's "Germany for Germans").
As a further dig, the Stooges, who were all Jewish, threw in a variety of Yiddish in the dialogue.
Some powerful congressmen who were either pro-Hitler or pro-neutrality were incensed at this short, but Paramount went ahead and released it anyway, resulting in Moe being the first American actor to portray Hitler in a released film production.
The Stooges were a remarkable trio. One of the high points of my life was meeting Larry Fine. He was in a wheelchair from a stroke, but still had his sense of humor.