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Loss and regret in the small hours: Bob Dylan’s Shadows in the Night

Shadows in the Night by Bob Dylan

A lovely little bauble in Bob Dylan’s vast catalogue, the new Shadows in the Night is both a big surprise and a logical next step.

It’s logical because Dylan has always been a consummate cover artist: from his early days in New York City, when he was pretty much a Woody Guthrie clone (and proud of it) to the cover versions of any number of blues, gospel and rock songs (some standards, many fairly obscure) that he’s played live to the covers-only records he’s made, such as 1993’s World Gone Wrong, Dylan has always made songs by other people his own – to the point that there has sometimes been criticism leveled at him (and which he has angrily responded to) that he’s put his own name on songs that were just slight rewrites of other people’s work.

The surprise here is not so much that Dylan has recorded a bunch of songs from the great American songbook – God knows he’s put his own stamp on just about every other genre – but that he sounds so relaxed and assured doing it. A record of deep feeling but music that often sounds as though it’s barely being played and sung, Shadows succeeds largely because Dylan’s voice is up to the task – which, really, is something that nobody could have expected at this late stage of the game.

Dylan’s voice has long been derided, but in recent years, as anyone who has seen him in concert can attest, his vocals were often little more than a dry, cracking husk, unsteady, weak and, at times, actively painful to listen to. As someone who first saw Dylan in 1978, and who has seen him at least once and often twice every decade since, I can say that the power and vitality of his voice has diminished to a horrific extent over the years, to the point that even some serious fans – as detailed in David Kinney’s excellent 2014 book The Dylanologists: Adventures in the Land of Bob – have suggested that he simply retire to save himself and his fans further embarrassment.

And yet here he sings with a soft, relaxed assurance, his vocals caressing the lovely melodies and sad tales of The Night We Called It A Day, Autumn Leaves, Why Try to Change Me Now and seven more, often sharing the stage with nothing more than Tony Garnier’s bass and Donny Herron’s magnificent pedal steel guitar. Shadows makes good, and then some, on its premise: Dylan doing the great American songbook, jazz-pop tunes popularized largely in the 1940s and ‘50s by such writers as Irving Berlin, Johnny Mercer, Rodgers & Hammerstein, and more.

These are torch songs, come-back-to-me songs, tales of grand regret and heartache, stories of men who have had love, have lost love, and are now wandering the dark corners of their minds and their memories. They are some of the best songs of the 20th century and they simply don’t work – they cannot work – without the singer giving them tremendous empathy and not a small amount of pathos; we have to believe that the guy singing them believes them, and has invested in their stories completely

And, again and again, Dylan is equal to the task. Listen to how he sings “But I miss you most of all, my darling/When autumn leaves start to fall,” or “There wasn’t a thing left to say/The night we called it a day” with the poignant regret of a man who knows the love he lost was the love of his life. Or how he brings to life, in That Lucky Old Sun, a poor man’s knowledge that the only peace and rest he will get is when he’s laid in the grave. Or the rueful, sweet self-examination of a man growing older and lonelier he brings to Why Try To Change Me Now.

Sometimes it’s the singer, and sometimes it’s the song, as the saying goes, and in this case, it’s both: Dylan brings a warmth and empathy to this music that simply cannot be faked, a wonderful intimacy that easily helps us overlook the times, here and there, that the voice goes a little flat, or he just barely misses a note he aims for.

He is, like all great vocal interpreters, marvelously alive in these songs, and they breathe and float with him as he moves through them, one part old friend, one part cypher. He knows the people in this dark landscape of pain and longing, knows them in his bones and the memories of his own life.

He’s leaning in now, and you’re right there with him. He needs to tell you these tales, and you need to listen, before the bartender calls last call and the band packs up and we all have to go home, alone, to our lonely beds and our memories of what once was and what might have been, until the first flecks of grey appear in the east.