Bill Kelly
17 min readSep 3, 2022

BOB DYLAN: THE OUTSIDER COMES HOME

Bob Dylan has been an outsider and I think he still feels like one despite his Nobel Prize and all his fame. He once talked about having been born in Hibbing, Minnesota to a family and environment where he just didn’t fit. He wondered why he was born there. How strange! Obviously, he had to get out. But it was good for him in the sense that otherwise he might have wasted precious time finding out something he always knew: growing into the image of his parents and his society wasn’t all that it was cracked up to be. He had to get on with the discovery.

In the early days of his music career, the many sides of Bob Dylan were just Dylan coming out with whatever part of himself could respond to what was going on. But he was always the same restless person looking for a kind of freedom that is rare in a society in which people are hemmed in by their organizations and by their jobs. Even more dangerous are the boxes that people place themselves in so that they don’t feel alone, so that they have a “solid” idea of who they are, and so that they don’t have to continually grow and shift and change and face the unknown. You could call Dylan’s approach to life at that time a cult of spontaneity.

Instead of planning life and calculating and trying to get the most with the least effort which is what so many people were reduced to, Dylan focused on being present and alive to every new thing as he discovered that big world out there. He was open to what helped him to be more real, more free, and to avoid the chains that bind. His good fortune was to gain the wealth and fame that allowed him to stay clear of all the entanglements that can easily bring a person down: having to make a living, getting the right educational credentials, building a successful career, navigating personal relationships, setting up networks. He didn’t have to work on Maggie’s farm no more; he didn’t need 20 years of schooling just to work on the day shift. He could contemplate and create.

High and Low

Dylan was coming up when the boundaries between high culture (“art”) and pop culture (“commerce”) were beginning to crumble. He brought together the folk artist, the voice of a community, and the Beat Generation writer who shook up the intellectual establishment by leaving behind sterile forms. His center, his only reality, was his experience; abstract ideas, systems, and received versions of reality had no appeal. Dylan and the symbolist poets shared a preference for drugs as a vehicle of visionary experience which let the mind break loose from civilized restraints.

By doing drugs, the young people of Dylan’s generation realized that the world was not as hard, clearcut, and material as they had been taught. There were other channels that the mind could tune into. Dylan was looking to find a language and sound quality that could capture the subconscious world and make it intelligible without falsifying it. It was an exploration of the self to find what felt truer, closer to who one really was, which was what many middle-class youth were after. Don’t focus on externals like money and status; only care about living people, the immediate, what could be experienced. Dylan was helping people who were waking up to themselves to make sense of what was going on.

To the extent that we can believe Dylan’s own account in Chronicles: Volume One, we learn that he started out with a typically American “passion for dumbness.” But when he encountered literature at a place where he stayed, he didn’t hesitate to joyfully devour serious book after serious book on the shelves. Thucydides’ stories gave him chills and the insights into human nature and the use of words struck him as totally contemporary. Beyond history, he appreciated the power of Faulkner and found Balzac funny as well as a fountain of philosophic insight. Dylan also admired the poetry of Byron, Shelley, Longfellow, and Poe, as well as the dark Russian genius of Pushkin, Tolstoy, and Dostoevsky. He even read Clausewitz and renewed the morbid fascination with the military life he once had in Minnesota.

The counterculture included both the New Left, the minority of political activists, and the freaks, the majority faction that was living out a cultural revolution. Dylan could have such an overwhelming influence in this milieu because he found a third way between the sentimental and shallow commercial culture and the remote and largely inaccessible high culture. His music reached a large audience despite being oppositional because young people too were searching for alternatives. The sociologist Herbert Gans in Popular Culture and High Culture maintained that for a time there was an opening between commercial culture and high culture but then the counterculture media was swallowed up by popular mainstream media. Dylan was no longer the voice of a generation as soon as that generation broke up.

What happened? In a place like Berkeley in the late 1960s, Dylan’s “The Times They are a Changin” seemed to broadcast the self-evident truth that “the loser now will be later to win,” But the Reagan era came instead. People found their own mixtures of rebellion and conformity, the simple life and the consumer game, and some were plain exhausted by the backlash they had to face. Meanwhile, Dylan continued on his own winding path which even detoured into evangelical Christianity during the late 1970s and early 1980s. But Dylan has tried to set the record straight by saying that he has always believed that there is a higher power. At the same time, his true religion is his music.

An American Artist

Bob Dylan is very American. After all, he had almost no interest in the musical traditions of other cultures with the important exception of Kurt Weill and felt that American blues and folk were the ultimate music. He also saw Woody Guthrie as the absolute leading edge of music and gave Robert Johnson’s blues credit for helping him get free of the constraints that would’ve held down his own songwriting. Even more to the point, he was intimately connected with traditions of American music like country and western. In fact, many lines and melodies in his songs were taken from earlier musicians, and he reworked them and turned them into something new.

Robert Johnson

His link with the Beats was that he was inspired early on by Kerouac’s hipster notion of looking for kicks and by his lively poetic phrases that sounded like bop. He became good friends with Allen Ginsberg in the mid-1960s. Like the Beats, Dylan was an artist first and a poet of consciousness rather than an activist. He sympathized with outsiders and free spirits who found their own way beyond the well-worn grooves of conventional American dreaming. There was also African-American music: Dylan appropriated the styles and songs of bluesmen like Robert Johnson and blind Willie McTell. He appreciated the undersides of American life — it was where he found free people.

Dylan made country music inviting to listen to even for city people. A song like “I’ll Be Your Baby” was a winner; it had warm and soothing words: “Kick your shoes off, do not fear, bring that bottle over here, I’ll be your baby tonight It was a time when young people were letting down their guard and opening up to the other freaks whom they treated as kinfolk.

The country songs of Dylan’s album Nashville Skyline, though, were hard to place. His voice was so smooth and clear that the emotion seemed less genuine. Interestingly, Dylan himself once said in an interview that his voice suddenly became beautiful because he stopped smoking. He really did write “Love is all there is, it makes the world go around.” How was this different from conventional mainstream love lyrics? Where was the alternative edge that the counterculture loved? Of course, he had the right to come out with anything he wanted. In fact, he did a whole album of “standards” in the 2010s, songs that Frank Sinatra had belted out. But when he sang such songs, it often induced a nostalgia for rock and folk music and the writing of the Beats among his early core following.

No More Finger-Pointing Songs

Dylan was always willing to go off in new directions and take on new challenges. It would’ve been so easy for the young Dylan to keep writing songs that told stories of the suffering of underdogs (“The Lonesome Death of Hattie Carroll”), that promised revenge or comeuppance to the obscenely greedy and power-hungry (“Masters of War”), that empathized with the ongoing tragedy of black Americans (“Blowing in the Wind”), and that punctured the balloon of American hypocrisy and righteousness (“With God on Our Side”). Yet, Dylan stopped mining this vein of pure gold that he had briefly tapped. In “My Back Pages,” he saw his finger-pointing songs as a time of moral absolutism that he had left behind. “Good and bad I defined these terms quite clear, no doubt, somehow. Ah but I was so much older then; I’m younger than that now.”

Recording Bringing It All Back Home album

One thing Dylan recognized was that the people in opposition, the liberals on the side of the good, were just as trapped by their own programs, their own boxes, their own orthodoxies as the people they opposed. He totally supported the ideals of the civil rights movement and felt a personal connection with the people in SNCC who were out there organizing voter rights drives and marching for freedom. But the liberal establishment was another matter. For these privileged people, civil rights was an identity, a badge of honor, an “us” against “them” cause. They were up tight and not personally free. Dylan did not want to be part of a movement or an organization; he would not sing what people wanted and do what the good people were doing.

The Electric Dylan

It was special that after his folk period Dylan went on to open up a rich vein of music that was in sync with the times. He got to the bottom of so much of the 1960s generation’s experience, at least the New York version of it. Although he hated to be singled out as anything more than a performer of songs, he expressed the chaotic world inside many young people.

A few examples will have to suffice, although Dylan poetically and precisely expressed so many aspects of that experience: disgust with mainstream hypocrisy, the lyrical aspects of alienation and life beyond the pale, the feeling of nowhere to go and no place to take refuge, and the relentless negation of what was held up to be sacred. From “It’s Alright Ma” there are the lines, “Although the masters make the rules for the wise men and the fools I’ve got nothing ma to live up to.” It was pretty clear about how he felt to be one small person subject to a vast machine. From “Like a Rolling Stone” an obvious choice is “When you got nothing, you got nothing to lose.” In “Mr. Tambourine Man,” Dylan tells what it was like to be at the end of the rope, “My weariness amazes me, I’m branded on my feet, I have no one to meet, and my ancient empty streets too dead for dreaming.”

And how about these lines from “Desolation Row?” “Yes, I received your letter yesterday, about the time the doorknob broke. When you asked me how I was doing, was that some kind of joke? ” That was how it felt in the desolation of many minds. These may have been fairly common experiences but the lyrics that expressed them were unique. Dylan himself said that the words and images in “Desolation Row” just came through him. To cite one example among many: “And Ezra Pound and T.S. Eliot fighting in the captain’s tower, while calypso singers laugh at them and fishermen hold flowers.”

Who Was This Guy, Anyway?

Dylan had said it all, but he didn’t make it easy for people to idolize him. And that was the last thing he wanted. Yet Scaduto’s early biography pictured him as self-centered and success-oriented, a guy who used people. Maybe the abuse he suffered from fans when he went electric plus the intrusions into his privacy, the stupid questions, and the occasional lunacy of his counterculture admirers were a karmic balancing of accounts. However, in Scorcese’s 2005 documentary No Direction Home, Dylan’s commentary was right on the money when talking about his early music, neither defensive nor full of himself. His weather-beaten face and wry interpretations of the old Greenwich Village scene were a winning combination.

There was a hard edge to many of his songs, “Positively Fourth Street”’ being an obvious example. The nastiness of “It Ain’t Me Babe,” where the edge cuts very sharply, hits very close to home. The singer charges the hapless beggar for love with wanting “someone who will die for you and more.” Some other very fine songs like “Don’t Think Twice” (“You just kind of wasted my precious time”) and “Just Like a Woman” (“She fakes just like a woman”), and “Like a Rolling Stone” displayed an animus against women. Yet, during the same period, Dylan could write “Love Minus Zero” which celebrated the Zen wisdom of the woman he loved.

It was not hard to prefer Joan Baez to Dylan for her antiwar activism and willingness to sacrifice. She was no saint, but she was far more idealistic and concerned about other people than Dylan. Remember how badly Dylan treated her in the mid-1960s when she joined him in Great Britain and he wouldn’t even let her perform on stage. Yet she had given him that chance back when he was still getting established.

Bob Dylan and Joan Baez

But Dylan was not unfeeling. He did a lot for Ruben Carter so he could get out of prison. His memorable song “Hurricane” of the mid-1970s told the story of a black man in New Jersey — what it was like, the injustice he faced. It also revealed his own feelings of shame about living in America, a land where black people are obviously framed and where justice is a game. Compare these feelings with his response to the George Floyd murder by police in 2020: “It sickened me no end to see George tortured to death like that.”

A Mature Wisdom

In 1975, Dylan’s album Blood on the Tracks and songs like “If You See Her Say Hello” showed he had matured and was really singing from the heart. Some of it might be attributed to the breakup with his wife that appeared to have wounded him where it hurts the most. Dylan tries to put on a brave face but the pain comes through, and he is far from getting over the separation and split with his wife. “Tangled Up in Blue” had an attractive sadness, and not just the energy and relentless motion that it shared with earlier Dylan songs. The singer tells the story of the links of destiny between himself and a woman. He keeps moving on, unable to forget her. Their going separate ways was not anyone’s fault; it was just different points of view.

If we go back to the first few years when Dylan and his wife were together, it was the time when he wrote the very long and obscure but haunting “Sad-Eyed Lady of the Lowlands.” Critics liked the song and Dylan once said it was his best song, but what is a listener to make of it? It is about a woman, loosely based on his wife perhaps, an extraordinarily elusive woman whom no one can take the measure of. But what is the singer’s attitude toward her? She has aspects of the inanimate but is also gentle. Do the following lines sum up her relation to the singer?

Now you stand with your thief, you’re on his parole

With your holy medallion in your fingertips now enfold

And your saintlike face and your ghostlike soul

Who among them could ever think he could destroy you?

Then there’s the refrain which acknowledges the woman’s gravity but so much can be read into it because there is so little that is concrete to go on.

Sad-eyed lady of the lowlands

Where the sad-eyed prophet says that no man comes

My warehouse eyes, my Arabian drums

Should I put them by your gate, or sad-eyed lady should I wait?

It ultimately comes down to the sound, Dylan’s inimitable voice, and the atmosphere that these unfathomable lyrics create. The refrain stays in the mind. It might make you reflect on the unknowable mystery of a human being, especially a woman who has so fully fashioned herself, an artist of the self. And you might further imagine what it must be like to intimately relate to such a woman.

The Lean Years

The lean years lasted from 1971 to almost the end of the century as his audience dwindled and the critics put down much of his work. Let’s say that his output was uneven. But Bob Dylan’s Greatest Hits: Volume Three is an enjoyable and rewarding way of getting a snapshot of where Dylan was from 1971 to 1991. “Tangled Up in Blue” and “Hurricane” stand out, however, in the last song “Knockin’ on Heaven’s Door,” Dylan’s music and voice are unforgettable as he evokes the mind of a frontier lawman giving up the ghost in just two short verses.

During the lean years, Blood on the Tracks in 1975 was the highlight album, and the 2019 Scorcese movie Rolling Thunder Revue shows just how dynamic and intense his performances could be during the mid-1970s. This was Dylan at his absolute singing best. He organized a low-key tour along the lines of the traveling carnivals he once saw back in Minnesota. The wearing of masks and costumes and having colorful characters and improvised dialogue was an idea Dylan got from the Italian commedia dell’arte troupes of the early modern period. Until Dylan got distracted by real-life events, it was a remarkable creation with great performances. And a mellow community formed among the musicians and participants, many of them famous and most of whom dropped by only for a while.

The Comeback Album

The iconic rock magazine “Rolling Stone” chose Dylan’s Time Out of Mind as album of the year for 1997. Dylan could still tell stories but the stories he told were bleak. Give Dylan credit, though, for not taking refuge in self-deception and for continuing to search and seek out new experiences. The most powerful song is “It’s Not Dark Yet” which puts it all out there and creates an atmosphere; its mood is stoic. He knows how to get across with simplicity and candor what people often feel but don’t want to face as they move toward the end of their lives. But lines like “I ain’t lookin’ for nothin’ in anyone’s eyes” make the singer sound so jaded.

For those who go through a brutal experience of love for a woman, Dylan’s song “Lovesick” from Time Out of Mind gets it oh so right. In a live performance, Dylan sings softly and wistfully with occasional anguish before desperation ultimately appears. The music is somber and recurring chords suggest inescapable fate. In the instrumental part, guitars cry and mourn and then sound like the crashing of out-of-control thoughts in the mind.

The song is filled with contrasts: the singer’s tired feet and his wired brain, the dead streets and lovers in the meadow, a silence like thunder. There is his innocent childlike love destroyed by a smile as he sleeps. He is so drawn to the woman and yet wants to forget her and wishes he had never met her. And most of all, there are questions. “Did somebody lie? Did somebody cry? Could you ever be true? I wonder about you.” On top of that, he doesn’t know what to do. The pain of separation meets the reality of betrayal; the need for an answer is crushed by the realization that there isn’t any.

Dylan is admirable for focusing on what the pain of transient love is like rather than just blaming the other or hating himself. He clearly understands how sick love can make a person. The album is grim, but it faithfully reports actual experience. To what extent did it represent his?

The Kennedy Assassination

In 2020, Dylan made some waves with the song “Murder Most Foul” about the 1963 assassination of President Kennedy. It was spoken to music, lasting 16 minutes, and there were so many references, predominantly to musicians from a variety of genres, but all of them American. Dylan intended it to be a gift to his fans who had supported him all these years. But what was the song getting across and how is the JFK assassination connected to the musicians whose names he rattles off? There is a little, but not much interpretation of what the event represents. It goes like this: Since Kennedy’s death, it has been the time of the Antichrist and slow American decay. The assassination was the place where faith, hope, and charity died.

Dylan also throws out a lot of cliches which takes away from the solemnity. Maybe JFK is happy where he is now since only the dead are free. It seems like we are all lost here. Yet the accumulation of songs that Dylan mentions can give us comfort. Dylan’s rendering of the assassination is that evil and implacable forces are in control of this nation’s destiny when the chips are down. But they are faceless and nameless, personifying the dark forces of our nature.

The story is spun out of so many associations that it feels like whatever conclusions one draws are the product of one’s own assumptions and preconceptions. The outlook seems pessimistic. We are pawns in a larger game, whether it is being run by a small secret group or is the implacable workings of forces we can hardly comprehend. The listener’s mind might run toward Shakespeare rather than Wolfman Jack as the spinner of the story.

Dylan said in a recent interview: “Every human being, no matter how strong or mighty, is frail when it comes to death.” That fits JFK perfectly: he was at the very height of power and then in a moment he was gone. The message I get from Dylan is that we need to be humble and not too proud or confident of the power and glory we have attained.

“Murder Most Foul” is one more example of Dylan’s willingness to go off in his own direction and do something unheard of.

John F. Kennedy

Containing Multitudes

“I Contain Multitudes” is on the same Rough and Rowdy Ways album as “Murder Most Foul.” It mentions Dylan’s many sides. A line about his being a man of many contradictions and moods is amply borne out by the song itself. It first appears to be a love song since he pronounces “I’ll lose my mind if you don’t come with me” although it is sung a bit tongue-in-cheek. At the end, he says he will only reveal his hateful side to her and unceremoniously tells her to get lost and get up off his knee and keep her mouth away from him. Yet he declares right afterward that his mind is open — he’ll leave no love behind and will play some Beethoven and Chopin piano music. Is this a sign of containing multitudes or the ravings of someone whose hold on the “real world” is tenuous?

A cosmic overtone creeps in: “I sleep with life and death in the same bed.” Dylan compares himself to those notorious bad boys, the Rolling Stones who went right to the edge where what we have lost is redeemed. When Dylan says he apologizes for nothing, although he is all too aware of his many unseemly qualities, he appears at peace. Blake’s Songs of Innocence and Experience is his prototype, and like Blake, he is inhabiting another dimension, one without sequential time: “Everything is flowing at the same time.”

Dylan says he wrote “I Contain Multitudes” in a trance, like many of his recent songs. “The songs seem to know themselves and they know that I can sing them, vocally and rhythmically. They kind of write themselves and count on me to sing them.” He identifies what he writes with his real feelings; he doesn’t have any second thoughts.

In the mid-1960s, who could have imagined this is where Dylan would wind up? Yet the trip from the surreal to the “supernatural” may not be so long and strange after all. Dylan has accessed another level of consciousness which the surrealists pointed to in their automatic writing. Let go of conscious control and access the deep unconscious and be whole.

Bill Kelly

American, 24 years abroad. Interests: philosophy, intercultural communication, spiritual practice, Asia. Author of A New World Arising