Bob Dylan’s Triplicate is the next piece in the perplexing puzzle that is his recent discography

Fans of Bob Dylan know they’re following a seasoned, knowledgeable time traveller. His is a restless, critical artistic mind that surveys his immediate surroundings and determines whether he’s going to engage with contemporary life head on or instead draw on historical precedents that might inform us now. Somehow, his records and their meaning seem eerily prescient.

Since the early 1960s, Dylan has rumbled forth as the most intricate lyricist and boldest singer to compose original popular music. Most musical genres have borrowed from him. But at various stages of his professional life, he has paused to sing the songs of others, usually on a cluster of albums.

The latest iteration includes 2015’s Shadows In The Night and 2016’s Fallen Angels – each stellar, not-quite-big-band explorations of the American songbook. It’s seemingly capped off by the first triple record in his catalogue, Triplicate.

This series of records has been well-curated by Dylan, mixing familiar classics with deep cuts sung, or that might’ve been, by his early hero Frank Sinatra. Triplicate is a little more obscure than the others: The Best Is Yet to Come, As Time Goes By and Stardust are the best-known of the 30 jazz-infused pop songs, but it doesn’t really matter what you’ve heard before.

Dylan, his ace band, a horn section and arranger James Harper imbue new mystery into these old songs, captured live off the floor and organized into three thematic 10-song sequences. Moody and alluring, the album can be enjoyed by just about anyone, anywhere. But for a Dylan fan, it’s the next piece in the perplexing puzzle that is his recent discography.

Released in 2001 on 9/11, “Love & Theft” (a genuine masterpiece) explored America’s history of cultural appropriation, racial exploitation and mechanical production and consumption after the Civil War. On the record’s Bye And Bye, he tellingly sings, “Well, the future, for me, is already a thing of the past.” It’s an almost conspiratorial line maybe we’re living in a some kind of perpetual hindsight simulation. 

Dylan followed up that course with a more current survey he emphatically, perhaps deceptively, called Modern Times. By 2012’s Tempest, his most recent collection of original songs, he employed an unearthly snarl, bitterly growling lyrics like Pay In Blood’s “Another politician / pumping out the piss!”. Even with Obama in office, he had a bad feeling about the cyclical nature of American progress and, well, now here we all are, staring at the humiliated place with uneasy disgust.

Humanity, civility, decorum, empathy, respect and the lack thereof have long been topics that Dylan has explored in his work. Triplicate and its two predecessors address them again, calling back to bygone American eras – ones whose neurotic insecurity bore overcompensated cockiness – and determine that some sentiments may only ever get to rest on shaky ground.

You can hear allusions Dylan has made to some of these lyrics in his own work over the last few decades, which makes the collection all the more revelatory. And he sings as gorgeously and clearly as he possibly can, as if it’s more important to him than ever that we feel his love.

Top track: There’s A Flaw In My Flue

Bob Dylan and his band play the Air Canada Centre on July 5. See listing.

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