Best of the Academy Awards: Introduction and Rules

So my first series in the post-Oscar lull, is compiling my Best of Oscar Winners. Compiling all the winners of the Academy Awards from the various categories from the first ceremony up until this year's winners, I will then pick which one I think is best in a head to head category for each category. I will first present all the possiblities in each category, then narrow down to 10 to 15 finalists depending on the category (for example, there are only 11 Animated Feature winners, so 15 is not possible). Here are some of the groud rules:

1) It must be an Oscar winner, not a nominee.
2) It will feature the current categories, but will include all previous names of categories, as well as Special Achievement winners in older ceremonies.
3) If categories were once separated (Like Art Direction and Original Score), they are now combined.
4) Will most likely not do Doc. Feature, Foreign Language Film, or the Shorts, unless I get on a movie watching spree, as I simply do not know enough of them to make it a fair competition.
5) These are my personal preferences, so it is obviously subjective.