Here's a list of the ten best Donald Duck cartoons from a real fan. And if you've never seen Donald's only Oscar-winning short, Der Fuehrer's Face (1942) you can watch it on YouTube.
The Disney and Warner Bros characters used to get Oscar nominated a lot in the Animated Short category. In the past couple of decades the closest thing we have to a perennial in that category is Wallace & Gromit or Pixar as a studio, if that counts, though their characters don't repeat.
You know what I think is a crying shame as animated short films go? That Who Framed Roger Rabbit (1988) didn't really become a franchise. Disney made three short films with the characters after that blockbuster hit: Tummy Trouble, Rollercoaster Rabbit and Trail Mix-Up though none were nominated at the Oscars. They had the misfortune of arriving in that stretch of a dozen years or so when there were never more than 3 nominees in that category.*
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