Bob Dylan is “dwelling inside his personal hell” on his latest album. But the lament doesn’t come from Dylan’s pen in 2017 but from composer Arthur Schwartz and lyricist Howard Dietz, who published “I Guess I’ll Have to Change My Plan” in 1929 at the start of the Great Depression. Yes, for the third straight album—and this time, on a three album set—Dylan is tapping the Great American Songbook. While that opening track demonstrates a thoughtful curation, one still has to wonder: When will he release his own songs again?

Dylan recently told Bill Flanagan, in an unusually candid interview, that his new triple-album was in some ways inspired by Frank Sinatra’s late-career triple-album Trilogy. But the title Triplicate evokes not literary ambition so much as a business transaction, signed in three places to milk this old American cow as long as its nourishing dugs will allow him.

Though the connection hasn’t been as specifically made since Shadows in the Night, marketed expressly as a Sinatra tribute, Old Blue Eyes’ influence is evident here before Dylan ever opens his gravelly mouth. The opening bars of the arrangement for Dylan’s “I Guess I’ll Have to Change My Plan” come directly from the Nelson Riddle arrangement on Sinatra’s 1957 mid-career masterpiece A Swingin’ Affair.

It’s not the first Triplicate arrangement taken straight from a Sinatra recording; “Day In, Day Out” is based on Billy May’s chart for the 1959 album Come Dance with Me. They’re great arrangements, and, as Dylan is recording them with a live horn section, they have the relaxed mood of an old pro taking the stage at an art deco nightclub. But is that what we want from Bob Dylan? Much less three (or five) albums’ worth?

As Sinatra was then in transition from choirboy crooner to the richer timbre of his mature voice, so Dylan is evidently in the midst of a career change, eschewing his original wit for resonant standards. As his early career stood on the shoulders of folk and blues musicians; here he turns to his pop ancestors.

The elder Dylan now has the voice he always wanted when he was young; all the better to sell the life lived in old blues and folk songs. But as an interpreter of standards, he doesn’t always have the conviction even to sustain a single line; you can hear him lose interest in that opening track: “I went to reach the moon” peaks when he enunciates that heavenly body, but then he slurs the rest, “But when I got there/ All that I could get was the air.”

The vocal drop-off is a kind of interpretation, sure. Could Dylan be invoking the great promise of the moon landing and the subsequent disappointment in the nearly half-century that followed? Continuing the Sinatra homage, “September of My Years” was specifically composed for the 1965 album of the same name, an introspective collection to mark Sinatra’s turning 50. Old Blue Eyes’ voice was fraying then too, and Dylan is a full quarter-century older than that.

On the unfairly-maligned Self-Portrait, Dylan attempted the Great American Songbook on a sprawling album that in some respects was clearly a put-on. Sometimes Triplicate comes off as a lark, but that’s not always a bad thing: “Trade Winds” perfectly suits its tropical arrangement, the kind of unexpected cover that might be delightful in the context of a three-hour career-spanning concert. “Braggin’,” which originated not with Sinatra but with Duke Ellington, is a delightful mid-tempo swing that might have made for a livelier concept album. Sometimes Dylan hits an unlikely ballad on the nose: “My One and Only Love,” which seems like a song to be sung for and by the young, works as an autumnal, world-weary serenade.

Asked why he wanted to release three CDs at 32 minutes each, when the material would have easily fit on two CDs, Dylan replied, “It’s the number of completion. It’s a lucky number, and it’s symbolic of light,” and explained that on vinyl, the shorter albums means better sound for each disc. But you can almost hear his internal gravelly voice crowing, “It’s money, money money money, MONEY!”

There are worse Bob Dylan albums than Triplicate and worse examples of rock stars singing the Great American Songbook. Hell, this may be the best Dylan-does-standards album yet. But as there’s a good chance that Dylan fans thinking about buying this album don’t have all of Frank Sinatra’s classic Capitol-era albums, get any of those first—or get Self-Portrait.

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