AS BOB DYLAN sneaks into “I Could Have Told You,” the Carl Sigman and Jimmy Van Heusen number Frank Sinatra sang on 1959’s Look to Your Heart, he pulls against his band and time slows down. The steel guitar slithers in, and at first it sounds like a parody, a pretense of nostalgia — the Great American Songbook as insurmountable cliché. But then Dylan reveals a surprising, sunbaked, unaffected voice — reimagining the song with utter respect for its style, the world it evokes, and the skill required to create it. On Triplicate (and its two predecessors, Shadows in the Night and Fallen Angels), Dylan steals back, without so much as winking, the Greatest Generation’s catalog for a rock ’n’ roll audience.

Given our collective assumptions about Dylan’s singing, in which he smothers meandering lyrics with a manic, stylized attack, this vocal turn combines understatement with shock. Dylan, after all, rarely sings this out of character: on his classic material, he stretches out simple questions into menace, with elastic timings and vowel-bending distortions (“Can this really be the … end?”). Instead of imposing himself on Sinatra’s material, Dylan unexpectedly and quite thrillingly steps out of the way, allows the mood to gather around him, and gently massages these songs into a purr. Though the singer just turned 77 (born May 24, 1941), his recent efforts to echo the sounds of his parents’ radio — the sonic world his voice helped overturn — showcase some of his most distinguished singing and punctuate his catalog in a way nobody would have thought necessary.

Dylan’s sessions at Capitol Studios in Hollywood beginning in 2015 (before he won the Nobel Prize for Literature) stand as the most unexpected move in a career of reversals and double takes. He pulls a stylistic thread and a quilt of history unravels: since his days as King of Folk (alongside Queen Joan Baez), Dylan has played the gleefully unreliable teller of his own story. In any given song, on any given record, he’s commenting on where he’s been, where he is, and where he’s going. This proved thrilling early on, when he swerved at warp speed through rock’s asteroid belt. No sooner had he mastered folk did he write a farewell to that oeuvre that still works as an ode to spent innocence (“My Back Pages,” 1964). Once Dylan started singing rock ’n’ roll on Bringing It All Back Home (1965), it was almost as if the music had pointed toward his obdurate phrasing all along, in the hidden moods of Gene Vincent’s “Be-Bop-A-Lula,” or the manic stutters in the Trashmen’s “Surfin’ Bird.” Throughout his genre tours (his country, gospel, tough-rock, and soft-rock phases, on down through collaborations with Tom Petty’s Heartbreakers and the Grateful Dead), Dylan’s ambition has proven total: his love for Americana trumps his love of any single genre.

II.

Struggling to explain the travesty of Dylan wearing a sequined jacket on Street-Legal’s back cover in his 1978 Rolling Stone review, Dave Marsh remarked how this abomination only made sense if you understood how badly “Dylan has always wanted to be Elvis Presley.” If tilting his Midwestern Jewish cowboy persona toward Vegas gave pause, Marsh implied, blame it on Elvis and shoot out your TV set. Presley himself always wanted to be Dean Martin (“As Long As I Have You”) at least as much as Marvin Gaye wanted to be Nat King Cole (“It’s Only A Paper Moon”), which proves how far out of touch rock heroes can be with their own strengths.

Dylan conquering Sinatra’s turf finds him honoring the aesthetic and political world he capsized. In the Tin Pan Alley era, figures like Sinatra and Bing Crosby depended on outside songwriters for material. (The hustle for songs and arrangements created intense intrigue among backstage players.) Peter, Paul and Mary’s 1963 rendition of “Blowin’ in the Wind” made Dylan’s name famous before anyone heard him sing; alongside Lennon and McCartney, Dylan turned songwriting into the new benchmark for originality (even “authenticity”); later, even as people complained about his peculiar deliveries, he wound up his own best interpreter. Rock transformed how singers chose and interpreted songs: many found Dylan’s delivery mannered, twisted, uncannily self-conscious in ways that detracted from his lyrics; many respected his songwriting long before they warmed to his utterly original (and complicating) vocal style.

Because Dylan never hinted at smooth sentimentality, people didn’t think of him as a Great Singer until his vocals turned inseparable from his songs’ meanings. Dylan’s voice crooks emotion the way a prism refracts light; he twists vowels like knives thrust into hypocrisy (“You just want to be on the side that’s winning”), and turns inelegant words into cackling poetry by mangling the odd syllable (“You’d know what a drag it is … to be you”).

Audiences splintered over this issue of Dylan’s singing. The simplistic notion that he couldn’t sing followed him around, like the generation gap’s crowbar etched in baritone: where parents heard nasal whining, the rock audience embraced an insubordinate stylist. Mitch Jayne, bass player in the Dillards, once said Dylan’s vocals sounded “very much like a dog with his leg caught in barbed wire.” Trying to explain your affection for Dylan’s singing traced the old critical distinction between the instrument and the musician, the voice and the singer. How could such a great political songwriter (“A Hard Rain’s A-Gonna Fall”) not command respect through his own interpretation of his own songs? Just as quickly, Dylan leapt out ahead of everybody again and applied his vocal gymnastics to blistering rock ’n’ roll, fusing his singing style with his songs’ meanings in ways few performers ever imagine.

III.

Dylan’s equivocal status as a singer (with a quirky yet inimitable voice) comes rushing back when you listen to him sing numbers like “Stormy Weather” and “That Old Feeling.” He sequences these five “albums” the way Sinatra did his during his defining “Wee Small Hours” period with arrangers Axel Stordahl, Billy May, and Nelson Riddle (primarily In the Wee Small Hours, 1955; Songs For Swingin’ Lovers!, 1956; and Come Fly with Me, 1958, many of these from sessions held between 1953–’55). Dylan’s Sinatra move, then, might just fit in with the whole willful Presley Vegas thread, except for how its tantalizing pull creates more tension than even Presley’s lust for Dean Martin. Triplicate underlines Dylan’s Nobel Prize with an air of sage longevity that overturns duds like Christmas in the Heart (2009). That holiday washout stands as the disastrous dress rehearsal for this masterpiece.

When rock ’n’ roll first dented the pop charts with Little Richard and Elvis Presley in 1955, it overthrew “literate” music (written and performed by educated musicians who could read and write notes). Folk musicians of all stripes, starting with R&B and Country-and-Western, and moving on to Woody Guthrie folk, swiftly dominated the charts for the remainder of the decade, upending the established hierarchical structure of the entertainment industry and sending Hollywood into years of perplexity. Sinatra called the new style “the most brutal, ugly, degenerate, vicious form of expression,” a comment blistering with class elitism: nobody with a college degree would ever fall for this stuff — this raw, simplistic, sexually reductive shadow foil to show tunes.

Once again, establishment (literate) culture underestimated the promise of folk and rock, which lends sardonic overtones to Dylan as music’s new “Chairman of the Board.” What’s more, it’s nigh unimaginable to flip the script — to picture Sinatra (or his ilk) ever making a decent album outside the safe boundaries of his more staid genre limitations. Put it another way: Could Sinatra even come close to pulling off a Dylan song? This, too, makes Dylan’s recent material sound slier, more suggestive, more preternatural.

Dylan plays the elderly quixotic with such aplomb that he avoids the genre’s pitfalls: there’s not a whiff of careerism in these numbers, and nothing announces Nobel Winner Sings Frank. We’re left instead with a man alone with his band, singing numbers his subconscious has rehearsed since childhood, with a depth and achievement that almost makes a hundred mediocre albums melt away. Alone in the studio with Charlie Sexton and Dean Parks on guitar, Tony Garnier on bass, and George Recile on drums, Dylan strips the songs of all their pretense and glamour. As Donnie Herron’s pedal steel blows smoke rings around Dylan’s voice, this core material accrues a gentlemanly dignity that mocks the old “urbane sophisticate.” Dylan’s renditions almost make Sinatra sound precious — gussied by strings, glossed by horns, adorned like flashing Vegas neon. By contrast, Dylan sounds naked, crisp, unfeigned — at once subtly deliberate and achingly spontaneous.

A conversation erupts between these sometimes eccentric selections and Dylan’s own material. “It’s Funny To Everyone But Me,” by Jack Lawrence, made famous by the Ink Spots (and then Sinatra) in 1939, sounds like an answer song to “Idiot Wind” — how that lover might respond to Dylan’s scorched-earth tirade. From Dylan’s mouth, “It’s the joke of the century,” sounds less comic than fated. And “When the World Was Young” somehow summons up “My Back Pages,” “You’re Gonna Make Me Lonesome When You Go,” and “Blind Willie McTell” as a humble — and humbling — meditation on the reproaches of history.

Throughout these tracks, the feeling of the song renewing the singer becomes a metaphor in itself: as the Presley audience now joins its World War II parents on the parade grounds of Jung’s collective unconscious, age turns time into a mystical reverie and pretense itself fades into the ether. In Irving Berlin’s “What’ll I Do,” where a young man questions his own existence after the death of a lover, Dylan channels a lifetime of genre-hopping and the rich pageant of singers who pegged their careers to such songs. Like an old radio crackling to life by catching a stray signal from beyond the spheres, it makes Dylan sound wiser than his years — and younger than any song.

¤

Tim Riley is the author of Hard Rain: A Dylan Commentary (1992) and several other books on rock history, and has taught cultural criticism at Emerson College in Boston since 2009. His website is timrileyauthor.com.