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.


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.


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.



Bob Dylan’s vocal instrument is not what it used to be but it’s still an expressive tool of great subtlety and power — still capable of the raspy lyricism of a Louis Armstrong or the growling fierceness of a Charley Patton.  Armstrong and Patton were of course two of the greatest singers of all time, even though you wouldn’t describe either of their voices as dulcet.  Dylan in his later years has taken his place in their company and his new album Shadows In the Night proves that.

Dylan is no longer capable of the effortless crooning he could pull off when he wanted to in his youth, so there’s something conceptually exciting about his decision to make an album of songs suited to a crooner — songs from The Great American Songbook associated with Frank Sinatra.


In the 50s Sinatra himself moved from sweet-toned crooning to a more conversational and dramatic approach to songs, but his pipes had never been better.  Dylan shows what you can do with a Sinatra song without the pipes — with timing, inflection, breath, total emotional commitment.

Total emotional commitment is the key factor — the sort of embrace of a song’s dramatic meaning that puts the singer in its service without reservations of any kind.  Dylan once said that Sinatra was one of the only singers who sang without a mask — meaning, I think, without the stylistic flourishes that distance a singer from the purely expressive task at hand.  (This wasn’t always true of Sinatra, but it was almost invariably true of the albums he recorded for Capitol in the 50s.)


Dylan sings without a mask on Shadows In the Night.  To call the results astonishing is to put it mildly.  Part of what’s so moving about the album is that Bob Dylan, an iconic rebel, a great though eccentric songwriter in his own right, surrenders utterly to the lyrics and the melodies of songs written for mainstream audiences.  It’s his way of honoring the greatness of these songs, honoring them in the highest way possible by giving them everything he’s got as an artist.

The songs Dylan chose for the album are mostly slow and melancholy numbers — songs of longing and loss.  When Sinatra recorded his best versions of these songs he was a man in the prime of life, which gave his expressions of longing and loss a particular kind of poignancy.  Dylan sings them here as an old man, which gives them another kind of poignancy, the poignancy of longings for things that may never be possessed, losses that may never be recovered.


Dylan has said that he knew he could never measure up to Sinatra’s performance of these songs, but he knew he had something of his own to bring to them — something Sinatra didn’t always bring to them when he grew old, when his instrument began to fail.  In his later years Sinatra got saucy and flip with standards at times — he put on a stylistic mask in that sense.  (Listen to Sinatra’s last recording of “Some Enchanted Evening” done for his own label Reprise, a song Dylan sings so sublimely here — Sinatra’s last version is an upbeat, jazzy rendition that completely eviscerates the emotional burden of the song.)

Dylan, standing shockingly exposed, cuts deep on every track of Shadows In the Night — cuts to the bone, carves these old songs into the fleshy tablets of the heart.  They have an unsettling intimacy — as though Dylan has decided to sit you down in person in the booth of a deserted saloon and tell you how things really are, how they’re going to be.



Singing is often about making pretty sounds, but not always.  Sometimes it’s just about breaking your heart.  When a singer’s instrument starts to fail, when the dulcet tones don’t come so easily, you find out what he or she really knows about singing.  Every breath, every inflection, every hesitation has to count — the way things will count on judgement day.

Bob Dylan knows everything there is to know about singing.  Listen to this album and take a lesson in the art and craft and mystery of it.

Click on the image to enlarge.