Mary Poppins, 1964
This Disney classic likely stood a better chance with the Academy, given that it was also a musical starring an effortless charming British actress (in this case Julie Andrews). Perhaps the fact it was a Disney film based on a children’s book, about a governess who brings magic into the lives (literally and figuratively) of a troubled family, was held against it, because Ms. Poppins actually grossed more money than My Fair Lady that year.