Saw Milk last night, Slumdog today. Doubt a week ago.
Enjoyed both movies, but really made me wonder how the hell could anyone compare these to say which is the better film?
I found Slumdog by far the most enjoyable, but in no way would i say that equates with the best example of its craft.
Or am i putting too much thought into what is essentially a popularity contest? 
I presume you mean Oscar films, not Emmy films.
You could ask this question of every category in every creative award in existence. People often do. There is no answer. You either accept the fact that people like giving awards and receiving awards or you don’t.
This. It’s not like the Academy comes to an agreement and they all say, “this is the best.” They vote. Winner wins.
Bear in mind that the purpose of the Oscars is not, at heart, to reward the “Best” of any category. Even they know it’s often an impossible call. Hell, George Clooney said so while he was accepting an Oscar.
The purpose behind industry awards - Oscars, Grammys, the awards your local radio stations hand out to each other - is to garner publicity for themselves. The Academy Awards bring a huge amount of attention onto the movie business, and that means money for the movie business. It gets people paying attention to movies, wanting to rent movies and go see movies.
The same way I compare wines: I hold up both of them side by side and whoever has the prettiest label gets to come home with me.