Sinatra was known throughout his entire career for his ability to convey the emotion of a song. Most good singers of the era would sing a song and the feeling you came away with was ‘hey, that guy’s a good singer’. But when Sinatra sang, most of his listeners came away not only with the feeling that the song’s protagonist was truly feeling the sentiment of the song, but also in a way that made his listeners feel they were along for the ride. If the song was lighthearted, cheerful and breezy (Come Fly With Me, for example), his singing of it could transport his listeners into a light, cheerful and breezy mood. You felt you were on that plane to Peru with him. Or if the song was sad or remorseful (One For My Baby) you would feel his sadness and lost love yourself. And if the song was triumphant, as with New York, New York or My Way, he made you feel the same grit and determination that the song’s protagonist was experiencing.
In my estimation Sinatra was and remains the best singer of popular songs who ever lived. I recall watching a special that CBS broadcast on what would have been Sinatra’s 100th birthday that had popular current singers doing renditions of Sinatra’s songs, and reading later that most if not all were terrified at the prospect when first approached – “You want me to do a Sinatra song?”. But they soldiered on and gave it their all anyway, and they came across like I said before – as good singers skillfully hitting the notes. But the emotional reaction within the listener’s mind just wasn’t there.
I think what some see as arrogance in Sinatra’s singing is really just confidence. The impression of arrogance is probably boosted also by his actions in private life, where often his behavior was indeed arrogant. But Sinatra had great respect for music and took it seriously, and the only times I’ve ever perceived arrogance in any of his songs is when the song itself called for it, as was the case with New York, New York and* My Way*, and yet even in these songs he inserts elements of wistfulness and sensitivity that counterbalance the arrogance.
I doubt that I would have liked Frank Sinatra in person. By most accounts he had a sort of Jekyll & Hyde personality and was either generous and charitable, or cruel and hurtful, as the mood struck him. And he seemed like a hard guy to stay on the good side of.
But when it comes to both technical skill and the ability to convey the emotion of a song so as to make the listener truly feel what the song’s about, he is in my opinion head and shoulders above everyone else.
I will say the two I think come closest are Tony Bennett and Willie Nelson. I’ve been a fan of Willie Nelson for a long time. Saw him in concert in the late seventies and to this day I consider it one of the best concerts I’ve had the pleasure to experience. Unfortunately, I think Willie missed the mark with this tune. His voice was part of the problem, as was the incongruity between the style of the instrumentation and the style of his vocals. I gave up on it half way through.