I just had a conversation with one of my loan officers about Frank Sinatra. In my experience, you either get Sinatra or you don't. I've talked to people who just don't understand his appeal, and if they don't get it, you really can't explain it to them. Sinatra was simply the coolest man on the planet.
I've long believed that I was born in the wrong era. I was supposed to be at the Sands in '64, hanging out with Frank and Dean and Sammy and Joey, drinking a martini and snapping my fingers as the orchestra locked in on a groove. And I love the word "dame". A dame, the way Sinatra used the word, was a unique woman, a woman who had a sense of her own power even before feminism came along, who could hold her own with any man verbally - what my father refers to as a "feminine tomboy", with wit and brilliance thrown in. Lauren Bacall was the quintessential dame of that era, and it's not a coincidence that she was the woman who named them the Rat Pack.
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I didn't get "it" with Frank until my senior year of college ... then it just sort of dawned on me one day while I was listening to "Fly Me to the Moon."
I still don't get the Beatles. At least, not on the gut level.
Eon: I am in the same position as you, but with a variation. I often thought that the Beatles were the worst interpreters of their own music. I also felt that starting with stuff like "I Am the Walrus", they were thumbing their nose at their fans. "We can record any old nonsense, and you twits will line up to buy it".
My favorite Sinatra is, oh, probably the stuff he did with Nelson Riddle. I grew up on it, and even at the age of 6, I "got" Sinatra.