Listening to this straight after In The Wee Small Hours, it sounds very much like an attempt to reproduce the concept of the earlier album - except that instead of losers in love, this is for winners. As a result, it is a much brasher, less subtle affair. It is also a less consistently-themed whole, but the famous songs - including those mentioned above, along with "It Happened In Monterey", and "Makin' Whoopie" (an entire song about sex! In the fifties!) - are so well-known that this is probably the more famous album. I think that's a shame.
Not that this isn't also excellent, but repetition of the same clichés spoils it a touch. The way that Sinatra slides up to notes is uniquely his, of course, but he does it so much - and clearly deliberately, because it's not hard to hear that he can hit a note dead on when he wants - and with such foghorn-like tonality, that it does start to wear thin. He sounds strained when going for the big notes and the joviality can sound forced. I think he's much better at quiet songs.