I don't know if this is of any help but, there were 3 major periods in Sinatra's career. Most people seem to like the Nelson Riddle years. As for me, I prefer the Count Bassie period.
Sinatra - good vs great
I don't have a lot of exposure to Sinatra, but my first CD was "The Reprise Collection: The Very Good Years." It's (well, they are) an awesome performance. Even the tunes I don't particularly care for have me tapping my toes. It seems to be very involving. Based on this - I was surprised that I liked it as well as I do - I bought a copy of the Captiol Singles collection. (This is the 4-CD set, not the mammoth 21-CD version!) The new set is nice, but it's nowhere near as involving, and I can't really put my finger on why. Some of the tunes are the same. It was done earlier in his (later) career, so I doubt that it's just that he had "figured it out" - he had long ago done that. Anyone know why this one CD is so much more enjoyable than the other set?