Observing the fealties of rock-music enthusiasts, I’ve sometimes been struck by an apparent contradiction in terms. To a fan, which individual musician or group of musicians you follow is often a matter of pure chance: you happened to hear them somewhere and decided to investigate further. But once you’ve attached yourself to the artist in question, your loyalty can easily turn obsessive. So do we say that your liking for your hero or heroes is a profound—sometimes even a spiritual—connection? Or, bearing in mind that you could have developed an equal passion for a quite different performer had you been similarly exposed to their music at a suitably impressionable age, should we dismiss your devotion as an essentially random turn of fate?

Somehow I’m always reminded of this enigma when reflecting on the life and times of Bob Dylan, who celebrated his eightieth birthday this year. In the course of his sixty-year career, Dylan has attracted more than his share of zealous and at times mildly demented followers, many of whom would seem to have clung to the object of their adoration with the tenacity of a pit bull having fastened itself to a trouser leg. His devotees appear to straddle all boundaries of age, class, and mental sophistication. Although Dylan himself, perhaps wisely, has always discouraged the minutely intense parsing of his lyrics, no such restraint is embraced by the paying listeners, critics, and academics who long ago greeted him as the latest all-knowing “youth spokesman” to appear over the horizon.

Perhaps the most obvious example of this last-named category is the now eighty-seven-year-old Sir Christopher Ricks, the British-born professor of humanities at Boston University, who has written a number of erudite books and essays seeking to elevate “the voice of the 20th century” to canonical status alongside Shakespeare, Milton, and Tennyson. In nearly every Dylan song, Ricks finds either “explicit correspondence” to or “structural echoes” of the work of classical poets. Thus the 1969 single “Lay, Lady, Lay,” a slight if mildly engaging air composed of a recurring four-note guitar phrase, becomes an exercise in what Ricks terms “erotolayladylaylia,” whose roots he traces to John Donne’s poetic undressing of his lover “Elegy XIX: To His Mistress Going to Bed.” Similarly, Dylan’s sing-along anthem “A Hard Rain’s A-Gonna Fall” (which its author later revealed had nothing whatever to do with nuclear fallout but was about “the lies people get told on their radios and in their newspapers,” thus anticipating what we would now term fake news) becomes a variation on the seventeenth-century Scottish ballad “Lord Randall.” One could go on. It’s worth dwelling on Professor Ricks, a man of many other sterling qualities, if only to illustrate the widespread infatuation with Dylan that seemed to seize many of the West’s places of higher education around 1963 and that shows no sign of abating some sixty years later.

A Gaunt, Elderly Man in the DoubleTree Inn

It remains one of the sorriest disappointments of a writing life not wholly untouched by shadow that I’ve never had the opportunity to interview Bob Dylan formally, having been consistently rebuffed by his “people,” but as it happens I can at least claim to have locked eyes with the great man on the same number of occasions as his lifelong champion Professor Ricks: once. It happened in the unlikely setting of the DoubleTree Inn in Missoula, Montana, where I was staying with my family in August 2012. It’s a perfectly agreeable place of lodging, if not somewhere you would normally associate with a globally famous rock star. The hotel’s distinguishing characteristics are a wooden carving of a moose advertising its somewhat threadbare gift shop and a faint but discernible whiff of Fawlty Towers at the front desk.

Around three o’clock on a stultifyingly hot Friday afternoon, my eleven-year-old son suggested that we make the short trek down to the vending machine full of invitingly cold drinks and sugary snacks that he’d located in an alcove just off the hotel lobby. Our room was on the third floor. Halfway down the stairs there was a small landing furnished by a brown shag rug and a couple of ill-matched plastic armchairs dipped in stain repellent. A gaunt, elderly man was standing there, quite alone, and he silently looked up at us with dark, bloodshot eyes as we passed by.

In a movie, when you make eye contact with someone either significant or unusual, the camera lingers in close-up, everyone freezes, behaves histrionically. In reality, suddenly confronted with the curious or unexpected, people are silent and inarticulate. Part of my own emotion was one of embarrassment. The stranger on the landing was haggard and generally distressed looking. He was dressed in what appeared to be a thrift-store green nylon tracksuit, a ragged scarf was tied round his neck, and his frizzy gray beard was neither full nor neat. An ill-advised wisp of drooping Zapata mustache completed the ensemble. I find it best on these occasions simply to nod politely and move swiftly on, much as one does when confronted by a politician. The poor chap seemed not to make a fetish of his personal hygiene, I noticed as we brushed past.

By the time my son and I headed back upstairs about three minutes later, the man in the green tracksuit was gone. “Was he a homeless person?” my eleven-year-old asked, with a note of compassion that did him proud, once back in our room. “I would have given him our spare change if he’d still been standing there.” “Either that or Bob Dylan,” I replied glibly, thinking of the latter’s apparent taste for dressing down in public, almost to the point of suggesting destitution.

At that my son silently tapped a few keys on his iPad, consulting the list of forthcoming cultural attractions, such as they were, in our part of Montana. A moment later he gave a noise like a gas-main explosion, and we were both once more hustling downstairs to search for the grizzled-looking man with the Mexican mustache. Bob Dylan was performing at a venue just across the road from our hotel that night. My middle-school-aged son had narrowly avoided offering his pocket money to a multiple award-winning American singer-songwriter and a future winner of the Nobel Prize for Literature.

Of course, by the time we had navigated our way back to the landing, and then thoroughly scoured the hotel’s public areas, Dylan was gone. I don’t know why, but the whole encounter recalled the way in which Rowan Williams, the former Archbishop of Canterbury, once described the Creator Himself to me as a “fugitive presence”; or, on a slightly less exalted note, the basic premise of the 1998 feature Sliding Doors, and others broadly like it, which seek to illustrate the contingent nature of reality. Sometimes an apparently random decision such as whether to go downstairs for a Coke, and then to stop or not to stop to acknowledge a stranger loitering in an otherwise deserted hallway, can have significant consequences. Looking back on it, the whole thing strikes me as a quintessential Bob Dylan experience of its sort: it would seem he’s flesh and blood, just like we are, but that boundaries have been set for his appearances among us.

Latter-Day Dylan

Notwithstanding the recent enforced absence of live concerts, Dylan or his work have been ubiquitous in recent years: movies, CDs, books, exhibitions of his drawings, Victoria’s Secret lingerie commercials (yes, you read right), his extraordinary radio show. Yet he remains an elusive and often prickly sort of American celebrity, one unlikely ever to expound on his troubled path to the top or to invite the representatives of Hello! magazine into his beautiful home.

It appears he enjoys much the same status as a once magnificent but now ruined historical mansion of the sort one might visit out of residual curiosity and respect, whatever its current state of disrepair. With the best will in the world, it seems to me incredible that anyone could enjoy a latter-day Dylan concert on purely musical grounds. The old songs are regularly given new tempos and arrangements, and are often barely recognizable until you hear the chorus, if even then. The new songs are indecipherable. There are no video screens or flares or lasers, or any of the other standard modern rock-concert accessories. This admittedly may be a good thing, but it hardly enhances the consumer experience. Dylan himself rarely if ever directly addresses the audience.

The last time I saw him perform, if it could be called that, I paid a fee well into the three figures for my companion and I to sit in two plastic seats wedged in the upper reaches of a drafty ice-hockey stadium in suburban Seattle. The night’s headliner sidled on without introduction, positioned himself toward the side of the ill-lit stage, from where he appeared to us as a black dot, eschewed any between-song banter, and left the hall after precisely seventy minutes (the mandatory minimum stipulated in his contract, some attendees speculated), declining to return for an encore. At least in the vicinity of our alpine perch, the acclaim was unmistakably tinged with reproach.

And that voice. Incredible. Those of us who ply an occasional living writing about popular music soon come to terms with the fact that many or most of its leading practitioners fall some way short of virtuosity. Even so, Dylan is something special. The late Rolling Stone correspondent Lester Bangs perhaps put it best when he wrote that it was “as if sandpaper could sing.” Even back in the ’60s, Dylan habitually rendered his songs in a catarrhal rattle that could make babies burst into tears and the family dog leap up and begin frenziedly gnawing its own tail. “Grating” was the word Bangs used fifty years ago, a critical verdict the successive decades have done nothing to diminish.

And yet even now there’s something insinuating about Dylan’s early output. Too intelligent to lecture us outright about Vietnam or civil rights, his best songs were always more allusive than didactic. You get a sense from them of what was happening in the wider political landscape of the day without ever quite being able to put your finger on it. Dylan’s first rush of creativity leapt from the joyfully deranged to the apocalyptic, and back again, to produce a kind of 1960s primordial soup combining themes of love, loss, isolation, and faith, and the sense that the new, switched-on view of life took the form of a universality of existence that saw “straight” thinking, including most political opinion from extreme left to far right, as basically insane. It’s in many ways a seductive premise. Put a sufficiently robust backbeat to it and it can be an irresistible proposition. Where Dylan did seek to comment on his times, however obliquely, the results were nearly always remarkable, ascending on the tension between a mainstream American culture embodied by Lyndon Johnson and Barry Goldwater in 1964 and the postwar generation’s own contrasting hopes and fears for the future.

Robert Allen Zimmerman

The Dylan backstory can be quickly recalled. Born Robert Allen Zimmerman to a middle-class Jewish family in the port town of Duluth, Minnesota, he was to fall under the influence of the folk artist Woody Guthrie and then to drift across the country to begin singing and playing the guitar in Greenwich Village coffee bars. In September 1961, Dylan gained public recognition when Robert Shelton of the New York Times wrote, “His clothes may need a bit of tailoring, but when he works his guitar, harmonica, or piano and composes new songs faster than he can remember them, there is no doubt that he is bursting at the seams with talent.”

The breakthrough album was called The Freewheelin’ Bob Dylan, and it emerged at a time of profound national trauma. Released in June 1963 to initially modest sales, it would enter the Billboard chart, eventually reaching No. 21, in the weeks following that November’s events in Dallas. Unlike my peers in the likes of Rolling Stone, I’m always wary of dignifying too many pop-music hits as searingly astute or incisive commentaries on their times, as though that might somehow explain their commercial success. On the whole, it seems to me unlikely that many young Americans would have decided to drive out to their local shopping mall to buy The Freewheelin’ Bob Dylan, or any other album, because of its supposed allegorical insights into their culture. But it would be fair to say that Dylan’s songs, “Blowin’ in the Wind” prominent among them, struck a chord at a time when many people, in all walks of society, were struggling to come to terms with the murder of their charismatic young president. There was, too, the gleeful abandon of Dylan’s up-tempo songs, with their combination of a propulsive beat and mildly surreal, sub–Lewis Carroll wordplay.

Of course it’s axiomatic with Dylan that he would shift guises from record to record and perpetually keep fans and critics guessing about his next move. To call him the precursor to David Bowie as a pop-music chameleon would perhaps be to confer a flattering sense of consistency on a man who seemed to restlessly change his sound with each successive album in search of an elusive balance between the creatively relevant and the commercially successful. There are musicians whose last record is very like their first. Having learned their trade, mastered it for once and all, they practice it with little variation to the very end. Bob Dylan is different. If nothing else, he will be remembered for being fearless in his single-minded pursuit of what he thought his evolving craft required. Having set out his stall as an unvarnished young folk singer, he promptly reinvented himself first as a full-bodied rock and roller and then as a busted-heart country-and-western balladeer on Bringing It All Back Home and Nashville Skyline, respectively.

As if that weren’t sufficient border-jumping, Dylan also found time to cut the subversive, six-minute single “Like a Rolling Stone,” regularly placed at No. 1 on that eponymous magazine’s interminable lists of The Greatest Songs of All Time; to dabble in rootsy Americana with The Basement Tapes; to release a series of records of contemporary gospel music; and then to fall into one of his cyclical dormant periods before reemerging with 1975’s Blood on the Tracks, generally assumed to deal with his acrimonious first divorce but which Dylan himself always insists is not in the least autobiographical or introspective.

The first that the new MTV breed of rock-music fans would see of the spokesman of their parents’ generation would follow on July 13, 1985, when Dylan closed out the U.S. end of the day’s Live Aid marathon at JFK Stadium in Philadelphia. It has to be said that it fell some way short of a triumphant comeback. Dylan and his hastily assembled band, consisting of Rolling Stones guitarists Keith Richards and Ron Wood, apparently couldn’t hear a thing through their malfunctioning stage monitors. The acoustics weren’t much better for those of us in the audience. Dylan promptly broke a guitar string, which expired with an audible, cartoon-like twang, and the necessarily brief rehearsal process had apparently left his sidemen only dimly acquainted with the night’s chosen repertoire.

Grinning sheepishly, the conscience of the 1960s and his two heavily mascaraed cohorts were reduced to scrubbing their instruments like a group of haggard washerwomen halfheartedly wringing out some socks, while Lionel Richie and his all-star ensemble could be heard, and occasionally seen, rehearsing the show’s big finale, “We Are the World,” on the other side of a flimsy curtain billowing behind them. It was what the rawest amateur production might look like at your local high school auditorium. Put another way, you could be forgiven for thinking that you were listening to a Studio Sound Effects recording of a protracted car crash, or watching a slice of the sort of slapstick rock ’n’ roll revue made popular around that time by the film This Is Spinal Tap.

After a further fallow decade or so, Dylan’s next career resurgence appears to have begun in 1997, when he was hospitalized with a life-threatening heart condition. The realization that he was mortal like the rest of us was followed by his release of an unexpectedly good album. Time Out of Mind’s sales of a million or so may seem less than overwhelming when compared with the numbers routinely racked up by his greatest-hits collections, but it was enough to win Dylan a Grammy and to paste his face on the covers of both Time and Newsweek. As happens to most artists who endure long enough, it was critical reappraisal time. Before long, Dylan would climb into an ill-fitting tux to accept an Oscar for his song “Things Have Changed” from the otherwise forgettable film Wonder Boys, before going on to have the morbid good luck to release yet another album—his forty-second—on September 11, 2001. Entitled Love and Theft, like his 1963 offering it appears to have been seized on as a form of musically assisted therapy in those troubled days, because, objectively speaking, little else about it would have warranted its glowing reviews.

In due course Dylan followed this with Christmas in the Heart, a collection of fifteen seasonal songs so perversely eccentric at best, or uniformly awful at worst, that one could be forgiven for wondering if, like a marginally less abrasive version of Don Rickles, Dylan might actually take pleasure in abusing the people who pay money to listen to him. (It should be noted here that all the royalties from the record were donated to the World Food Programme, as well as a variety of other worthy hunger-relief charities.)

The sound of pop music’s most fabulously discordant voice groaning its way through “Hark! The Herald Angels Sing” would appear to have been just the latest stylistic departure for a man whose career has long been distinguished by genre experiments ranging from rock to country, folk, gospel, soul, and blues, with frequent excursions to the world of old-fashioned vaudeville, and most recently as a sort of rhinestone-clad travelling burlesque act. It’s one thing to eschew staid consistency for challenging new work, but for Christmas in the Heart? Surely all but the most devoted of Dylan’s followers would have wished to spare themselves the ordeal of listening to the album and instead to dispense with the middleman by making a donation directly to their nearest food bank.

Domestic Dread

It would be churlish to dwell at any length on Dylan’s private life, or to deny that at one time his drug consumption, promiscuity, and general truculence did indeed portend a cast of mind that would ignite the fires of creativity his admirers claim for him. In November 1965, he married Sara Lownds, with whom he had four children. In her divorce petition of March 1977, Mrs. Dylan remarked:

I can’t go home without fear for my safety. I was in such dread of my husband that I locked doors in the house, to protect myself from his violent outbursts and temper tantrums. . . . He has struck me in the face injuring my jaw. . . . My children are greatly disturbed by their father’s behavior, and the bizarre way he has elected to live.

Among Dylan’s domestic peccadilloes was a reported taste for well-upholstered young women whom his wife and children would periodically encounter at the family breakfast table.

In June 1986 he married Carolyn Dennis, a longtime member of his backing group, and had a daughter by her. Ms. Dennis continued to appear onstage with her husband, and the marriage remained a closely guarded secret until it, too, ended in a somewhat lurid divorce. Dylan’s second wife was to remark enigmatically that “Bob has been a wonderful, active father,” who has “eight or nine children.”

He apparently subscribes to no organized religion, although when praised by an interviewer for his “heroic performance” on Christmas in the Heart, which he supposedly delivered “like a true believer,” Dylan replied: “Well, I am a true believer.”

Once again demonstrating his unerring ability to appear before us at times of crisis, in June 2020, shortly after the global pandemic struck, Dylan released an album called Rough and Rowdy Ways. It was widely praised for its musical diversity and for the absurdist humor of its lyrics. I quote the London Daily Telegraph only to give a flavor of the critical consensus. “The wise old poet has stirred up a cryptic cauldron of truths and clues, philosophy, myths and magic,” the paper wrote. A few months later, Dylan sold his entire catalog of some six hundred songs for a price estimated at between $300 and $400 million.

If Bob Dylan had never existed, critics would have needed to come up with a synonym for the word “Dylanesque” to describe the sort of music represented by his best, caustic, yet perversely enjoyable mid-1960s output. Such things are subjective, of course, but had Dylan spent only four or five years at the top of his creative game, as I believe he did, it was enough to establish his persona as the most elusive, talented, and, in retrospect, influential American popular performer of the second half of the twentieth century.

No other such entertainer has so thoroughly challenged and transformed the commercial laws and artistic conventions of his time. In March 1962, the Billboard pop charts were still dominated by the likes of Connie Francis, Lee Dorsey, and Mr. Acker Bilk’s clarinet, not to mention Bing Crosby and others of his ilk who had begun their professional careers singing through a loud-hailer. Dylan’s eponymous first album, released that month—introduced by a rush of guitar and the line “I don’t know why I love you like I do,” delivered in a mirthless laugh—well and truly kicked open the doors of artistic perception. Even, or especially, as a young man, his best songs were smart enough to be quoted as proverbs.

Not the least of the many enigmas about Dylan is that, having come out of the gate as a much-needed corrective to the sugary melodrama of mainstream American popular music, he’s long since retreated into the role of a sort of touring curator of the otherwise forgotten folk-vaudeville material written for the most part by elderly men at around the time of the Coolidge administration. It may only be recently that he’s approached the status of the originals. One way or another, Dylan has already survived as a working musician some fifty years longer than the most charitable forecast made on his debut. It’s curiously tempting to bet on him lasting a few more.

Christopher Sandford is the author of biographies of Mick Jagger, Keith Richards, Paul McCartney, David Bowie, and other grandees of rock.