I could bore you all night on this one!
I adore Misissippi John Hurt. I recall saying on another thread that I don't understand all of his "Moaning The Blues", but I find it compelling and deeply affecting. There is a sort of a laugh and a bemused tolerance about the way his voice tells the stories. "Let The Mermaids Flirt With Me" has that melancholy humour down so perfectly.
I am surprised that Billie Holiday's name has not appeared here yet. She could take so many songs which I would normally be indifferent to and really make me care about them. I can't think of anyone who could make "They Can't Take That Away From Me" sound so moving yet uncontrived at the same time. She had a range of only about an octave and fifth - but what she did with it!