This version of the song is a classic, and deservedly so.  It’s from 1945, when Sinatra was most appreciated for his crooning — the smooth tones and easy delivery that made him a sensation, mostly with young girls.  You might argue that Sinatra is more concerned here with his star persona as a dream lover than with emotional expressiveness.  You don’t get a feeling he’s really broken about by being alone — more that he’s putting the moves on somebody to rectify the situation.

That’s niggling, though, in the case of such a lovely musical treasure.

Dylan’s cover of the song on his new album is something else again.

This is the voice of a man who’s gotten on a bit in years, who feels his isolation keenly.  His hopefulness is mixed with weariness and with rue.  His voice is not what it used to be, so he can’t use it to project a dream boat image, which makes his wishing and longing all the more poignant.  Dylan’s version cuts deeper than Sinatra’s and is a classic in its own right.

A pitch-perfect interpretation of this lovely song, both musically and dramatically.  Sinatra’s almost conversational tone, wistful and self-deprecating, is backed by a subtle and tasteful arrangement by Gordon Jenkins.  It’s one of the high points of Sinatra’s years at Capitol.

Dylan’s cover of the song on his album Shadows In the Night is nearly as good.  He also sings it in an almost off-hand way, bemused but perfectly sincere when he gets around to the song’s thematic climax, the matter-of-fact declaration of a love that’s never going to change.  Dylan has more miles on the odometer that Sinatra did in 1959, when he recorded the version above, so his interpretation is inflected with a bit more resignation, but both Dylan and Sinatra get to the heart of a miraculous entry in The Great American Songbook.

This is a brilliant version of the song, beautifully sung by Sinatra, but it’s not entirely convincing emotionally.  It’s from the 1956 Capitol album Where Are You? on which Sinatra worked for the first time with arranger Gordon Jenkins.  (He’d done most of his previous work at Capitol with Nelson Riddle.)

Jenkins went for a lush, smooth sound, less jazzy than Riddle’s arrangements.  Sinatra generally used Jenkins for sentimental ballads, closer to the feel of those he did with Axel Stordahl at Columbia earlier in his career.  He follows Jenkins’s lead here, delivering a lush, smooth vocal that favors the musical over the dramatic.

Dylan covers it on his album Shadows In the Night and brings the dramatic, melancholy side of the song closer to home.  It feels very personal.  When Dylan sings the opening line — “The falling leaves drift by the window” — he makes you believe they’re right there in front of him, prompting a reverie, reminding him of very specific regrets.  When he recalls “the sunburned hands” he used to hold, back in a lost summer of lost love, you sense he’s remembering the exact way they felt in his hands.

The falling of leaves in autumn is a familiar metaphor, a cliché, but not in Dylan’s rendition of the song — he summons up an image of real leaves that will eventually have to be raked into piles and burned.

This version of the song was recorded for Columbia Records in 1949, before Sinatra had his amazing breakthrough as an expressive artist at Capitol Records, where he began his legendary collaboration with arranger Nelson Riddle.

At Columbia he was still using his longtime arranger Axel Stordahl, whose backing of Sinatra could be a little syrupy at times.  Still, you can sense here the beginnings of the almost conversational phrasing and emotional directness Sinatra brought to his great work in the Fifties.

Sinatra recorded the song twice more in the Sixties for his own label Reprise after he left Capitol.  One was a decent but uninspired duet with Rosemary Clooney, the other a dreadful, punched-up hipster version which doesn’t convey even a trace of genuine emotion.

It’s easy to overlook how great the song is.  Many people think of it in the versions from the Broadway play and its film adaptation (above), in both of which it’s sung in an overblown operatic style that subverts the simple conversational perfection of the lyric by Oscar Hammerstein II.

Sinatra serves the lyric pretty well in his Columbia recording, but Dylan serves it perfectly in his new version on Shadows In the Night.  He makes it simple — you see a stranger who sweeps you off your feet . . . you need to go talk to her before it’s too late and you lose her forever.  Dylan sings about this as though he’s someone who knows all too well what it’s like to let a golden moment pass you by.

This song has a brilliant title — the lyrics are not quite so inspired, but Sinatra makes you forget that with his emotional commitment to the number.

Dylan covers the song on his new album Shadows In the Night and somehow improves on Sinatra’s version, dramatically if not musically, singing in a persona simpler than Sinatra could plausibly adopt.  The obvious images become convincing in Dylan’s rendition — bewilderment replaces sophistication as the dominant mode of the performance.

Dylan sings in the voice of an ordinary man leveled by a romantic catastrophe, searching about through the clichés in his mind for a way to express his devastation, failing to find it, and all the more bereft for that.

Trev Gibb and band, Newcastle Arena, a few days ago.

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.