Bob Dylan's third foray into songs previously recorded by Frank Sinatra isn't only the largest set of new recordings he's ever released (three CDs, 30 songs), it's also majestic in its own right. Dylan moves through this area – the region of Sinatra, and also of standards songwriters like Irving Berlin, Jerome Kern, Hoagy Carmichael, Richard Rodgers and Oscar Hammerstein – as if it's territory for him to chart and command. Indeed, Dylan has now made more successive albums in this idiom than in any other style since his world-changing mid-1960s electric trinity, Bringing It All Back Home, Highway 61 Revisited and Blonde on Blonde.
That's stunning – and not only because of the album's grand latter-day vision. When Dylan issued his first set of Sinatra-related songs, 2015's Shadows in the Night, the project reflected the history of American music's oldest cultural war; the songs Dylan chose for that album, and a follow-up volume, last year's Fallen Angels, showed how well he understood Sinatra and the rarefied "Great American Songbook" era of Tin Pan Alley and Broadway musicals. When the rise of outsider forms – country music, rhythm & blues, rockabilly – displaced all that in the 1950s, some reacted as if barbarians had stormed the gates. Sinatra was among them. "Rock & roll smells phony and false," he said. Dylan, though, had done something even more radical – maybe worse – and he knew it. "Tin Pan Alley is gone," he said in 1985. "I put an end to it. People can record their own songs now."
With the monumental Triplicate, he's certainly made amends. Though Dylan recently won the Nobel Prize in Literature for his own songwriting – that is, for how he expanded the arts with his use of language – songs have always been much more to him than wordcraft. Music itself carries as much meaning. A song isn't a song without melody, harmony and voice.
Time and again he proves the same thing on Triplicate. Though a handful of songs here are delightful bounces (including the opening track, "I Guess I'll Have to Change My Plans") and some easygoing almost-blues ("That Old Feeling," "The Best Is Yet to Come"), most are downbeat, spectral ballads. In songs like "I Could Have Told You," "Here's That Rainy Day" and "Once Upon a Time" – ruminations on a memory of loss that is now central to the singer's being – Dylan raises devastation to a painful beauty. Other times, he intimates something ghostly. In Sinatra's original 1965 version of "September of My Years," arranger Gordon Jenkins opened with an eddy of strings, invoking the tide that eventually rolls in for everybody. Dylan's band creates the same undertow effect, sounding just as full, with Donnie Herron's steel guitar and Tony Garnier's bowed bass.
When Dylan first decided to sing Sinatra, the idea seemed far-fetched. Did he have a voice left that was possibly up to it? Dylan made plain at the outset of Shadows in the Night, in the opening measures of "I'm a Fool to Want You" – the most defining of all Sinatra songs, and one of his only co-writing credits – he was better than up to it: He did the song dead-seriously, and chillingly. "Smooth" is not a word you would use to describe Dylan's weatherworn voice. But he can wield phrasing as effectively as Sinatra himself.
Dylan uses only a quintet throughout Triplicate, no strings, no big band (though there's a small dance horn section here and there). They re-create the solemn openings to "Stormy Weather" and "It Gets Lonely Early" in all but instrumentation. He's picked his repertoire -carefully and meaningfully here. Of the 50-some albums he released between In the Wee Small Hours, in 1955, and 1970's Watertown, Sinatra made about a dozen exploring loss, masterpieces every one. Dylan culls more than half of Triplicate's songs from those releases – particularly favoring Sinatra's often-overlooked last LP for Capitol, Point of No Return, from 1962.
He closes Triplicate, though, with something Sinatra sang many years earlier: "Why Was I Born," written by Kern and Hammerstein in 1929. It's a torch standard that epitomizes the sort of writing that Dylan killed off, asking the biggest questions – "Why was I born?/Why am I living?/What do I get?/What am I giving?" – on the most personal level. Dylan is no stranger to dejection or hard self-examination. What he understands here is the triumph in surviving that darkness. It's in that survival, and how you put it across to others, that you find out why you were born.
David Crosby sings the praises of Bob Dylan in a original animated video.