1940. dir. Charlie Chaplin, starring Charlie Chaplin, Charlie Chaplin, Jack Oakie, Reginald Gardiner, Paulette Goddard.
Seen it before? No.
OK, so, you know how Charlie Chaplin looked sort of like Hitler? Well, apparently Chaplin himself realized this, and thus the idea for this 1940 comedy. Chaplin plays a dual role: he is a Jewish barber who fought in WWI and suffers from amnesia, and he is "Adenoid Hynkel", the raging ant-semitic dictator. (A title card at the beginning announces that any resemblance between the barber and Hynkel is "purely coincidence", surely a veiled Take That at Hitler's rumored Jewish ancestry.)
It's partly comedy, and partly dead-serious drama about the plight of the Jews in Nazi Germany. The comedy parts are reminiscent of Duck Soup, but not quite as funny. Bonus points for timeliness though, and the guy who plays the Mussolini stand-in was a riot.
At the end of the movie, the barber and Hynkel have switched places, but Chaplin pretty much abandons both characters to deliver a pro-democracy monologue directly to the camera, On Deadly Ground style. It must have been pretty shocking at the time, considering the US wasn't at war with Germany yet. It's great that he took the opportunity to denounce fascism, but it sort of derails the movie. Also, the economy is still in a depression, and since when does making speeches about hope and change actually fix anything?
Position on the list: 95
Fake language alert: Esperanto is used for the signs in the Ghetto. All the German is obviously fake also.