Did any singer swing it before Sinatra? Not that I can find in ten minutes of internet research, and if that's correct, it's difficult to see how Riddle even thought to make this swing, but then he did it with so many old songs. It was part of his genius.
I can't say I connect much emotionally with the song but it doesn't really matter -- the singer, arranger, and musicians have created a jewel (though it's a minor one in comparison with some of the other songs from Swingin' Lovers) which holds up to hundreds of listenings. Frank and Nelson do their classic thing, amping it up the second time through, with Frank modifying the lyrics to add intensity, changing this:
Stars and steel guitars and luscious lips, as red as wineto this:
Broke somebody's heart and I'm afraid that it was mine
Stars, guitars, lips red as wineIt works. I'll leave it to someone more musical to describe what Riddle and the musicians do, but it works, too.
Broke somebody's heart and I fear that it was mine