Louis and Frank
I've got a much bigger soft spot for Louis Armstrong than I do for Frank Sinatra. My Sinatra love comes from his acting (From Here To Eternity's one of my favorite films of all time, and he's just breath taking in it) than from his singing career. I think for the most part, he spent more of his career over the hill than on top of it, so to speak. But Louis Armstrong... the guy was just amazing from birth to death. There's a bunch of early recordings from his first trip to Paris, playing in clubs, and you realize that the guy just plain knew where music was going, and how to ride that wave. Equal parts soulful and technical, Louis represented all of the potential of Jazz and Blues music, much of which, I've always felt has gone untapped since. He managed to be very much his own man, not letting his race, his bizarre voice, or his odd look stop him from taking his place as one of, if not the, greats in the history of music. That indominable spirit is so clear in every note he plays and every word he sings... So much so that you can actually see that rarest of things on the face of Frank Sinatra in the below clip... respect.