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Cuphead's ancestor - DrakeVagabond - 10-12-2017
The character that became Cuphead descended from a 1936 Japanese propaganda animated film where a man with a teacup for a head morphs into a tank. The Moldenhauers emulated the animation because they found it strange, and "right away it stuck". The brothers had previously tried a kappa in a tophat, characters with a plate or fork for a head, and about 150 different designs.
Source:
https://www.webcitation.org/6RWo1L6fT?url=http://killscreendaily.com/articles/where-did-cuphead-come/