Until he started recording standards from the Great American Songbook in 2015, Bob Dylan wasn’t usually brought up in conversations involving Frank Sinatra, the suave crooner known as “The Voice.” After all, Dylan’s own singing voice was once compared with the sound a cow makes when its leg is caught in a fence. Dylan and Sinatra’s music seemed worlds apart. Sinatra’s sound was clean, scored by the best orchestral arrangers; Dylan’s was dirty, with rough guitar playing, piercing harmonica, and a willingness to let mistakes go unchanged. Sinatra’s enormous recorded canon drew heavily on the Great American Songbook, which he helped formalize; the lodestar of our popular music, it defined public taste before being overthrown by rock and pop. Dylan, the rock era’s champion songwriter, mostly sang his own compositions, with words that broke from George Gershwin, Cole Porter, or anybody else who’d ever written American songs.

Their sensibilities didn’t align, either. They represented different things: style, swagger, vulnerability, on the one hand; prophecy, autonomy, mystery, on the other. One connected first with an audience of Greatest Generation teenagers and young adults, a cohort that came home after winning the war—the ones that lived—with lost innocence, and found that its generational singer could change with them, carrying them along out of that first, easy blush of youth and into the world of adult loves and losses. The other connected first with the folkies of the early Baby Boom, earnest college kids and peaceniks blazing the path of what would become the sixties. For them, he was visionary and incorruptible; they would learn painfully as the years passed that his incorruptibility consisted in his unswerving fidelity to music, not politics.

All these years later, Dylan is still at it, but now he is singing songs from an older time—the very songs, with those corny words, that his music had been designed to destroy, as one critic wrote. And at just the moment that he had become immersed in the music of his parents—the father that wanted him to work in the hardware store and the mother who wanted him to go to college—he had won the Nobel Prize in literature, a category-smashing event that sparked lots of commentary, pro and con, and, in typical Dylan fashion, probably had the award-givers regretting the whole damn thing by the time it was over. The Nobel brouhaha obscured a little-appreciated truth: Dylan’s prize-winning words mean the most when he sings them. (“Nobody sings Dylan like Dylan,” as the saying goes.) His songs have been recorded by hundreds, perhaps thousands, of artists, but few artists possess his gift for bringing words to life, insinuating meaning not through shouting or grunting—the rock singer’s crutch that Dylan walks without—but through a mastery of inflection. “He conveys so much, and I’m not sure how,” one non-Dylan fan, a singer herself, once told me.

As it happens, the 52 standards that Dylan has now recorded—on Shadows in the Night (2015) and Fallen Angels (2016), followed by the three-disc Triplicate in 2017—demonstrate some of the “how.” Dylan’s voice is in better form than has been heard in years, and the recordings are clearly not nostalgic tributes but vibrant reworkings of songs from a bygone age.

In his day, Sinatra was lauded for the care and attention he brought to the lyrics of songs. He would read aloud the words before recording, not commencing until he was satisfied that he had found a way in. We can hear that attentiveness on “I’m a Fool to Want You,” widely interpreted as a lament for Ava Gardner, Sinatra’s second wife, whom he divorced. On the 1957 recording, Sinatra sounds tormented, especially on his second time through the bridge that begins “Time and time again/I said I’d leave you,” in which he draws out the word “said,” emphasizing his powerlessness to make good on his vow. Gordon Jenkins’s orchestral arrangement gives the song a cinematic feel. It is a powerhouse Sinatra performance.

In his rendition, Dylan practically growls the song’s opening line, and it seems that any comparison will be a rout. Yet he goes on to show the traits that make him a fascinating singer. Like Sinatra, Dylan puts everything into the song’s memorable bridge but steers his inflective powers more broadly, italicizing certain words for effect, as when he sings, “Then would come a . . . time when I would need you,” a phrase that he sings differently each time.

Matched up with Sinatra vocally, Dylan is the proverbial Volkswagen in the Indy 500, but he brings certain advantages. Sinatra’s recordings of these songs span a quarter-century, from the late 1930s to the mid-1960s, with different orchestras and arrangements and different voices, whereas Dylan recorded them all over a few years’ time, with many of the same musicians and the same basic voice. His approach is thus more consistent, and often more effective when compared with some of the earliest Sinatra recordings, where the young singer is still finding his footing. And Dylan’s lived-in voice sounds ravaged by time and loss in ways that Sinatra’s more polished instrument cannot.

On other songs, Dylan is just more engaged. Sinatra doesn’t seem deeply committed to “Why Try to Change Me Now,” but Dylan gives the song a personal stamp, no doubt taking puckish delight in its title, and in lyrics like “I’ve got some habits even I can’t explain” and in the song’s signature line, which asks, “Why can’t I be more conventional?” Sinatra practically speaks the line, giving it no special emphasis. Dylan doesn’t overplay it, adding only a slight pause before the key word, but we get the winking self-reference to a half-century of spurning habit and expectation.

Sinatra’s technical purity can seem dated in places. On “What’ll I Do,” he is exquisite, bringing his self-described “18-karat manic-depressive” consciousness and “overacute capacity for sadness as well as elation” to a song anticipating lost love. But he also enunciates the syllables like a diction coach, especially on the word “photograph,” which rings oddly in the contemporary ear and distances us from the singer. Dylan’s less formal delivery brings us closer. His voice on “What’ll I Do” has never sounded so tender, and his tenderness somehow expands the song; the way Dylan sings it, one can imagine a broader canvas of losses.

He wouldn’t be Dylan without some paradoxes. Repeated listenings to his evocative “The Night We Called It a Day” cannot reveal why he would invert the referents in the song’s bridge, which Sinatra and others sing as: “Soft through the dark/The hoot of an owl in the sky/Sad though his song/No bluer was he than I.” Dylan sings instead, “Sad though his song/No bluer than he was I,” erasing the lines’ dramatic contrast—the word “though” makes no sense in this formulation—and downplaying the narrator’s suffering. Confusion, or Dylanish subterfuge?

On Triplicate, Dylan’s performances of some signature Sinatra classics—“The September of My Years,” “Stormy Weather,” “I Could Have Told You,” “Once Upon a Time,” “Here’s That Rainy Day”—are particularly rewarding when played back-to-back with the master’s own. “Once Upon a Time,” a gem salvaged from a middling 1962 Broadway show called All American, is a standout of Sinatra’s 1965 September of My Years album. Sinatra’s voice is at its richest and most expressive, and the arrangements, heavy on strings, fit the elegiac quality of the song: “Once upon a time/the world was sweeter than we knew/Everything was ours/How happy we were then.” One imagines what must have flashed across the minds of a generation of listeners in 1965 when Sinatra, who turned 50 that year, sang those words—their youths in the prewar years, the grind and loss and sorrow of the war, the technicolor optimism of the 1950s, all of it now “falling indelibly into the past,” in Don DeLillo’s phrase. (Fifty was old in 1965.) And then to hear Dylan, half a century later, in his mid-seventies, sing the melancholy payoff: “Once upon a time never comes again,” his ragged voice straining for gentleness—the sound of that effort, perhaps, a key to the effect he creates.

Dylan has become a living repository of American folk, blues, and country music, preferring what he, by his own admission, considers archaic forms—but in his recordings of the Sinatra standards, he is not a revivalist but a modernizer. The instrument of Sinatra’s era was the horn; of Dylan’s, the guitar. Dylan’s arrangements avoid orchestral trappings in favor of a small-group combo, with some embellishments here and there—a few horns, a viola, a cello—but mostly he sticks with acoustic guitar, bass, and drums (usually brushes). The Dylan band sounds country on some numbers, jazzy on others. The playing achieves an extraordinary intimacy that the Sinatra string arrangements, at least to my ear, don’t always manage—helped in part by how close-miked Dylan’s vocals are (you can hear him breathe). Sinatra’s accompaniment is the best of its kind—whether it’s Nelson Riddle or Gordon Jenkins or Harry James or Tommy Dorsey—but it can be intrusive, cuing emotions before the singer has earned such responses.

In the difference between Sinatra’s arrangements and Dylan’s one can trace a cultural history of the last half-century or so, in sound, and it is Dylan’s sound, for better and worse, that has won out: roughness over purity, vernacular over formality, suggestive and cryptic over direct and earnest. On Fallen Angels, Dylan records several songs from quite early in Sinatra’s career, several of which had opened with instrumental preludes that take their time before yielding to the singer—“Melancholy Mood,” for one, as well as “On a Little Street in Singapore.” Dylan’s band recreates these intros faithfully, but the different instrumentation is striking. “Singapore,” a slight but alluring romantic song that conjures the exotic, got the big-band treatment when Sinatra recorded it with Harry James in 1939; the horns dominate, and they’re fabulous, but the young Sinatra’s vocal seems almost an afterthought, a reminder of an era when singers were not the stars. Dylan’s band gets inside the song’s distinctive melody, using the rhythm section to powerful effect, and every vocal line is savored. Similarly, “Melancholy Mood,” another Sinatra/James recording, is defined by knockout horns. Dylan’s version begins quietly, with a bluesy intro, led by guitar, that doesn’t give over to the vocal until what seems like the last possible moment. When Dylan does come in, he has much to say—“Melancholy mood, forever haunts me/Steals upon me in the night/Forever taunts me/Oh what a lonely fool am I/Stranded high and dry/with a melancholy mood”—and he delivers it within about a minute’s time. It’s an effective bit of narrative compression, the instrumentation doing a good bit of the work.

Dylan’s band deserves much credit for making this ambitious project seem so plausible, and it serves him well when he squares up against the swinging Sinatra—a taller order than taking him on in the ballads, which make up the vast majority of the 52 songs. On Triplicate, though, Dylan branches out, ready to evoke the toe-tapping Sinatra holding a cigarette in one hand and a Scotch in the other. But “The Best Is Yet to Come” will probably convince few non-Dylanites. His gravelly tones don’t seem to fit here: it’s as if a rooster got loose in the ballroom. “You came along and everything started to hum,” he sings, and everything is humming—the band, certainly, but not the vocalist, who is too rough for this party. On the other hand, hearing Dylan do “I Guess I’ll Have to Change My Plans” and “Braggin’” (not recorded by Sinatra) can only be described as guilty pleasures. Who thought they would ever hear Dylan sing: “Why did I buy those blue pajamas/Before the big affair began?/My boiling point is much to low/For me to try to be a fly lothario,” or “Braggin’ ‘bout your fishin’/’Bout your horseshoe pitchin’/Bet you always keep the score/Talkin’ ’bout your mettle/That’s the kind they peddle/Down at the five and ten cent store”? Dylan’s cragginess wears well with these more lighthearted songs, even adding to the effect, and he lets his band strut.

For many, Dylan’s singing will always be alien and nonnegotiable; no amount of “character” or nuance can redeem that voice, the great interloper of our popular music. By these conventional measures, it’s hard to say that Dylan’s performances “beat” any of Sinatra’s, but Dylan’s compelling vocalizing breathes new life into these often-gloomy standards, and his arrangements render them in a more contemporary sound, bringing them all back home from the black-tie dinner and the Broadway show—not “covering” the songs but “uncovering them,” as he put it, “lifting them out of the grave and bringing them into the light of day.” Whether this is a good or a bad thing probably depends on whether you prefer Dylan or Sinatra—that is, if you feel the need to choose between them. Dylan was never one of those people. It’s “all music, no more, no less,” he once said. He really meant it, and you can hear it.

Photo by Keystone/Getty Images  (L), Christopher Polk/Getty Images for VH1 (R)


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