Charlie Chaplin made the Hitler mocking film, "The Great Dictator", in 1940 using his own money because none of the Hollywood studios were comfortable irking the Germans as they had financial relations with them. The film is said to be one of the greatest works of Charlie Chaplin.

The Interview Has Renewed Interest in Chaplin’s The Great Dictator, Which Is a Great Thing

One of the few good things to come out of this L’Affaire Interview has been a renewed interest among both the media and viewers in Charlie Chaplin’s 1940 classic, The Great Dictator. With some reason: If The Interview offers a cautionary tale in what happens when you satirize existing world tyrants, The Great Dictator is perhaps the poster child of satirizing existing world tyrants. Chaplin’s film, released before the U.S. had entered World War II, took direct aim at Adolf Hitler. In it, Chaplin played both the Tomanian despot Adenoid Hynkel (the film’s humorously named Hitler surrogate) and a Jewish barber who, after years in a military hospital, returns home only to discover that he’s now living in a brutal, anti-Semitic police state.

Source: https://www.vulture.com/2014/12/charlie-chaplin-great-dictator-history.html