Sinatra co-wrote and first recorded this song in 1951 — it’s said to be about his troubled relationship with Ava Gardner. The recording above, from 1957, with an arrangement by Gordon Jenkins, is one of the pinnacles of American popular art. Sinatra brings an emotional intimacy to his interpretation which is devastating, but he also sings beautifully, with a power that suggests he still might turn the hopeless love affair around.
Dylan covers the song on his new album Shadows In the Night with the same emotional intimacy but with a hopelessness and weariness that suggest nothing is going to get turned around — that the singer’s longing is just going to echo endlessly down through time. Dylan’s version is another pinnacle of American popular art.