There is so much to say about Sinatra. I use him constantly as an example when working with singers, not opera but musical singers. One can, and should, learn a lot from the white king of jazz, the short guy with the lazy voice. (I think he was my height, and also the same Fach (baritone).)
I make a distinction between receiving music as just sound, and receiving it as a package (sound, plus visuals plus thoughts about the music / song / artist). Admittedly Frank is somewhat of a package for me, which doesn´t mean that I don´t enjoy him also as just sound.
I must mention also what I call the Sinatra-effect; namely that (many) songs sung by Sinatra are so heavily associated with him that if someone else sings the song — My Way, New York, New York, Strangers in the night — the (adult) listeners think “Ah, a Sinatra song”.
He had a talent (genius) for making definitive versions of songs. He was almost a thief in that way, and that is what I admonish my singers to also be. Sing the song so that you own it, so that it is YOURS. Not like a library book that has to be returned within a month.
Enough pedagogics.
I will point to three darker Sinatra songs here. The first one, since it is Saturday night. “Saturday night is the loneliest night of the week” is a great self-pity song (at least once a week).
The next song I hated the first time we met. What a ridiculous song, I thought, silly organ and all. That was until I read the words, and started to listen to HOW Sinatra sings it. Then aversion turned to deep appreciation.
There is nothing nice or polished or “crooner” about this one. Sinatra sounds raw, naked, almost desperate, a natural fish in these gruesome waters. Ridin’ high in April, shot down in May…
The title of the third song is written on Sinatra´s gravestone, and might be written on mine too. “The best is yet to some” is not really dark but a slick, sophisticated, hard to sing Cy Coleman song with a fantastic arrangement by Count Basie. Try it at home, lovely intervals!
We’ve only tasted the wine / We’re gonna drain the cup dry.