This is a kind of synthetic folk song, like “Old Man River” — a Tin Pan Alley evocation of the existential laments found in the black musical repertoire.  “Synthetic” doesn’t mean phoney — it’s more like a paean to the sublime vernacular expressiveness of the spiritual and blues traditions.  You might see it as a form of minstrelsy, in which a white artist wants to say something he or she can’t say in his or her own persona but can say in blackface.

Blackface wasn’t always patronizing — sometimes it facilitated a profound and humble and loving tribute to black style, black culture.  The performance history of “That Lucky Old Sun” has transcended racial boundaries.  The best versions of the song have been done by black artists — Louis Armstrong, Ray Charles and Aretha Franklin — just as the best versions of “Old Man River” have been done by black artists.

Sinatra’s version above is way too white — it’s like an academic commentary on an African-American song.  It doesn’t enter into the black idiom the way the song’s (white) composers entered into it.  Bob Dylan, a white singer who has always had a special feel for the blues idiom, has performed the song a number of times over the years.

Above Dylan sings it back in 1985, when his voice was stronger and sweeter than it is today.  It’s a lovely performance but it’s got nothing on the version that closes Dylan’s new album Shadows In the Night, which is moving beyond my ability to convey, except to say that I’ve listened to it twice and it’s made me cry twice.

Black blues singers regularly performed, but rarely recorded, Tin Pan Alley songs written by white composers.  (Ray Charles, whose musical taste acknowledged no boundaries, offered his version of “That Lucky Old Sun” on an album that also included “Old Man River” and “Somewhere Over the Rainbow”.)  White artists have often been moved to try and sing the blues — with mixed results.  This is all part of the complex conversation of American musical culture.

Dylan’s version of “That Lucky Old Sun” on his new album is one of the most eloquent contributions to that conversation in the whole history of American recorded music.

Thanks to reader Ken for bringing the 1985 performance to my attention!

This is one of Irving Berlin’s most brilliant songs — a lovely melody with deceptively simple lyrics.  The iterated question “what’ll I do?” has a casual feel, but becomes an existential cry of hopelessness, particularly with this line — “When I’m alone with only dreams of you . . . that won’t come true . . . what’ll I do?”  That first ellipsis requires a subtle but perceptible pause to achieve the full impact of the line, suggesting a sudden realization or final acceptance of the unthinkable — this love affair is over forever.

When Sinatra first recorded the song in 1947 he didn’t make use of that pause — he was more concerned with delivering a mellifluous vocal performance than with plumbing the song’s emotional depths.  By the time of the 1962 recording above he’d grown as a dramatic artist and sang the line about as well as it can be sung.  Gordon Jenkins’s arrangement for the 1962 recording isn’t ideal, though — it’s a little overblown, going for emotional effects he should have left to Sinatra.

Dylan delivers a superb rendition of the song on Shadows In the Night.  He knows as well as the 1962 Sinatra how dark the song is and his aged voice gives it an edge that makes it even darker.  He doesn’t go for the pathos in the lyric in any obvious way — his phrasing, like Sinatra’s in 1962, is casual and straightforward, allowing Berlin’s words to take the song where it’s going . . . straight into a terrifying emotional abyss.

A brilliant performance of a magical song — one of the highlights of Sinatra’s years at Capitol, which were pretty much a non-stop parade of highlights.

Dylan sings it on Shadows In the Night with the same emotional commitment Sinatra brought to the song, though Dylan’s vocal doesn’t have the subtle perfection of Sinatra’s, with its mix of masterful musical calculation and dramatic intimacy. This is the one song on Dylan’s album to which Dylan doesn’t bring anything new.  His is just an excellent rendition of an excellent song.

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.