He will never be....
I fully expect to be accused of being part of the generation that "just doesn't get it," but in all honesty, I don't get Sinatra.
Musically, at least. Sure, the guy's persona was on par with the Most Interesting Man In The World. But vocally? People swoon over Sinatra as if he is the patron saint of baritones, and I just don't get it. It's not bad to listen to, not at all...but I've heard far more talented vocalists and don't get all the hype from a vocal point of view.
Classic era, classic music, classy pimp of a guy. Just don't know that he should be considered a vocal god amongst much better vocalists.