Commando Duck (Jack King, 1944)

Donald is a soldier whose mission is destroying a Japanese airfield. The Japanese soldiers naturally spot him instantly and all manner of mayhem ensues...

The short is a classic example of the many war-time propaganda cartoons made during the war and it contains many elements you would never see today. Amongst those is the overt racism which shows the Japanese as caricatures.

Der Fuehrer's Face (Jack Kinney, 1942)

Here we have an anomaly for its time and for that matter any time. It's original title was Donald in Nutziland but due to the enormous popularity of the song in it the title was changed to that of the song.

This short comes as something of a shock. Donald Duck is a nazi in it! Hitler, Mussolini and Hirohito are all featured as characters and Donald works at assembling cannon shells. It's impossible to imagine this being made today and it's no coincidence that it's never been publicly shown since it's original release.