Donald Duck, Chip and Dale - Out of scale
Chip 'n Dale first appeared in the cartoon Private Pluto (1943), though they did not have their names or distinguishing characteristics. Pluto has been assigned to guard a pillbox where the two chipmunks are storing their nut supply, with the large gun being used as a nutcracker. Chip 'n Dale did not get their names (or the traits that separate them) until the cartoon Chip an' Dale (1947) where they antagonize Donald Duck. They continued to appear in animated cartoons, usually annoying/terrorizing Donald, until the mid-1950s.