RowBuddy saidMy pick would be Frank Sinatra. He was/still is the most vocally gifted singer of the 1930s till the end of his heyday at the end of the 70's. He was still a good singer up till his death, but nowhere near as good as he was in say the early part of his career and his return in the 60s. Also, he NEVER used Autotuning or ProTools as neither were invented. That was ALL him. Finally, he was very well known for his interpretation of the lyrics and his feeling. You wont find an American Idol or Glee Ham that can SING like that with their emotional range of a rock.
I would put his best decades in the 1940s and first half of the 50s. And he was indeed remarkable. But a question like this requires we define what kind of music we are talking.
The great popular singer of the 1930s was Bing Crosby. But I've always maintained that the voices that resonated best with the public (if you'll forgive the pun) in the early days were those that worked best with the recording and broadcast technology of each era.
I happen to love a rich baritone voice, and in the 1950s it was Howard Keel for me, in those wonderful musicals he did. And of course there are operatic voices, that are just spectacular, they leave me more breathless than the singers themselves.
I occasionally attend private recitals, by the voice students of my partner's sister, a retired opera singer herself. All mature men & women, I love to hear a good voice right in front of me, live and without amplification. Musical talent always astonishes me, I suppose more so because I have none of my own, whether it be vocal or instrumental.
A person can play the piano in front of me, or a violin, or sing, and I am reduced to tears at such beauty & accomplishment. And I suppose jealously, too.