Every year, we go to the movies to see these, and nearly every year, the best one is robbed by a flashier but less substantive Disney puddlemuck. Last year, the best one wasn't even nominated but was merely "commended." Even though it depicted Louis XIV's court as fat chickens! And the best of the nominated ones did not win. But this year, I'm confident that the Academy's insipid judgments will coincide with mine, because "World of Tomorrow" is so self-evidently excellent that no one can deny it. I don't know if it's better than the best of all short animated films (which did win the year it was nominated), "La Maison en Petits Cubes," but it's pretty close.
One of the strengths of this bizarre and charming genre is that the time constraint requires you to compress details, and the result is usually something like a visual parable. For some reason, this results in many films about, basically, mortality. Maybe animators just ask themselves, "If I had nine minutes in which to convey one point, what would be the most important thing to tell people?" and always answer, "Death." "World of Tomorrow" fits squarely into this tradition of cartoons meditating on mortality, but Hertzfeldt has the courtesy to offset all the moments when you'd otherwise cry with a joke, so that you end up not crying at all, and not knowing how one short movie comprised almost entirely of stick figures and floating lines and circles can be simultaneously so funny and so sad.
On the other hand, the Oscar winner might be "Prologue," because wow drawing so good that it doesn't even seem to matter what the point is.
UPDATE: But then I watched Hertzfeldt's long animated film, It's Such a Beautiful Day, and it was totally unremarkable.