The Great Dictator (1939)

Directed by Charlie Chaplin

It escaped no one that the infamous leader of Germany had a very similar appearance to one of the most popular entertainers of the day.  So what was Chaplin's reaction?  To make fun of him mercilessly of course.  Chaplin later said if he had known the true horrors of the Nazi regime he wouldn't have treated the subject as lightly as he did.  However, you have to give him a lot of credit for being one of the few voices openly criticizing the Nazis at this time.  It is a brilliantly made movie with some hilarious moments.  Some scenes are now more moving than intended knowing the ultimate fate of the Jews.