Story goes, Sinatra was growing disillusioned with his lack of creative control while signed to Capitol Records. So in 1960, he founded his own label, Reprise, with the lofty goal that any artist signed to Reprise would have 100% artistic control and own the rights to his/her music outright. Technically, though, he was still under contract with Capitol until 1962, so he ended up recording albums for both labels simultaneously, occasionally cutting the same song for separate releases, literally days apart.
During this period, Capitol also began re-releasing his late 50s hits on compilation albums to milk the cash cow while it could. Not to be one-upped by Capitol, Sinatra recruited Riddle to re-record some of his old favorites for release on Reprise; Sinatra's Sinatra was one of those releases. (The gimmick to beat Capitol: the re-recordings were in stereo–still a bit of a novelty at the time.)
Anyway, the reason I prefer the 1963 cut is because it swings a bit more. It's looser. Sinatra's delivery feels more playful and even more assured than the Swingin' Lovers version, which is saying a lot, because the '56 version is considered a defining performance.
And it's probably sacrilege to say this, but I prefer Dick Nash's ebullient trombone solo to Milt Bernhardt's original. Nash's take just has a little more flash and feels a little brighter. (Sinatra and Riddle actually had wanted Bernhardt on the '63 session, but the musician was booked for another recording.)
Long and short, it's a commanding, timeless performance that illustrates why people will still be fans of Ol' Blue Eyes in 2063 and beyond.
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