Decade of Dissent: Sean Egan on Bob Dylan’s Most Radical Years

An in-depth conversation about the myth, the music, and the man who reshaped a generation.

What happens when the most enigmatic artist of the 20th century crashes headfirst into one of its most turbulent decades? That’s the question Sean Egan tackles in Decade of Dissent, a punchy, insightful new book that zeroes in on Bob Dylan’s wild, brilliant run through the 1960s—a stretch where he didn’t just write great songs, he nudged the culture. From folk clubs to stadium stages, from protest anthems to surreal poetry, Dylan redefined what a musician could be and dragged popular music along with him, often kicking and screaming (popular music, that is). Egan’s take is sharp, passionate, and refreshingly unromantic. He cuts through the mythology and gets to the heart of what made Dylan tick during his most explosive period.

In the interview that follows, Egan gets candid about what drew him to this project, why Dylan’s “going electric” moment still sparks debate, and how the artist’s flair for self-reinvention kept everyone—including his fans (and maybe himself)—on edge. With stories pulled from interviews with key players, including musicians and photographers who were there in the thick of it, Egan paints a portrait of a Dylan who was equal parts genius and chaos agent, navigating fame, influence, and backlash with a mix of calculation and pure instinct. It’s a reminder that behind every reinvention was a real person grappling with the weight of his own legend—sometimes embracing it, sometimes blowing it to pieces.

What makes this conversation especially rich is how Egan balances admiration with honesty. He’s not afraid to question Dylan’s motives, critique the misfires, or highlight how media and fans alike often missed the point. And in doing so, he reminds us why Dylan still matters—not as a frozen symbol of the ‘60s, but as an artist who challenged his time and, in the process, helped define the present.

Evan Toth: How did you come to write a book about Dylan, particularly his 60s output? 

Sean Egan: A few years back I wrote a feature for a magazine on Highway 61 Revisited. I had the privilege of interviewing a lot of the musicians who worked on the album, as well as Daniel Kramer who took that wonderful cover photograph (as well as the cover photograph of Bringing It All Back Home, the previous album). As with any magazine feature, the bulk of the interview material didn't get published because you just can't fit it all into that sort of word length. It’d always been in the back of my mind that this might make a good book one day, or at least the basis of one, not least because I didn't only discuss with the interviewees that one album. This being the sixtieth anniversary year of Dylan going electric, I thought it would be a good time to utilize all that material now. I expanded the subject to take in the entire sixties, because that's the meat of Dylan's work aesthetically, as well as the point in time where he was at his most influential.

ezt: Dylan’s early persona was built on a myth of struggle, yet his upbringing was relatively comfortable. How did this tension between reality and self-invention shape his songwriting, and do you see it as a necessary part of his artistry or a form of calculated deception?

se: It was definitely deception insofar as Dylan invented this poverty-stricken, itinerant persona which was exposed by Newsweek magazine as fraudulent at the end of ‘63. However, his privileged background definitely shaped his personality and his political views. One of the things he detested most about his childhood was the fact that when he did odd jobs for his father – who owned a furniture store – one of the things he had to do was repossess furniture from people who could no longer keep up the payments because they'd been made unemployed. Eventually, this sort of sympathy for the underprivileged and the underdog fed through into some of the greatest protest songs of all time.

ezt: I’ve always been interested in Bob Dylan’s move from folk and protest to seeing and commenting on the world holistically, and providing his songs with a lot of context and ambiguity. Where do you believe he was led in that direction? Today, too, it seems that middle of the road points of view are often criticized, things are very black and white. Do you think that’s just the way the world is, or is it a similar trait indicative of time in the 60s and in the 21st century we find ourselves in?

se: You're basically talking about his transition from what he referred to as ‘finger-pointing’ songs to songs of greater nuance. I think it's something that we all go through in life whereby we stop seeing things in simplistic terms, but for Dylan it was an accelerated process simply because his brain seems to work five or six times faster than anybody else's. He entered wholeheartedly into the protest thing and produced The Freewheelin’ Bob Dylan and The Times They Are A-Changin’ but by the end of that period, which is little more than 18 months, he felt he'd exhausted it, plus he'd grown up a lot even in that short space of time. He just couldn't bring himself to write didactic songs anymore and so he moves onto things that really address the same issues of injustice and inequity but in a far more layered and self-critical way. ‘Desolation Row’, for instance, and ‘It’s Alright, Ma (I’m Only Bleeding)’. Things were indeed very black and white in the 1960s, which was a point in history where there was a vast chasm between the values of the young generation and the middle-aged and the old. We do seem to have gone back to such polarized viewpoints again, although I'll leave that to historians to judge why.

ezt: One of the things you point out in your book is that prior to becoming involved in the folk scene, Dylan really loved rock n’ roll. This maybe serves to question Dylan’s commitment to folk in the first place. Obviously, his changeover from folk to rock caused a stir at the time. What do you know about some of his early rock influences and how they clashed with his folk work?

se: He loved people like Elvis, Little Richard and Buddy Holly when he was a kid and didn't exhibit much interest in folk at all until he started playing in the coffee houses at university. He's also admitted to various people, including his high school sweetheart, that he switched over to folk because that was the only way he felt that he could make it commercially at the time. However, that doesn't mean he didn't fall in love with folk music. He had a vast repertoire of folk songs and of chords and you really can't fake the enthusiasm behind that depth of knowledge. The trouble is that when he moved back to rock and roll it didn't seem to his folk fans to be a matter of returning to his roots so much as selling out, because pop and rock were perceived as banal and vulgarly commercial by the folk crowd.

 ezt: Bringing it All Back Home and Highway 61 Revisited are two of my favorite Dylan albums: there’s a kind of howling freedom on those records that I think many people identify with and find excitement in. In your research, what did you learn about the reception of these two albums during their time? 

se: The reception wasn't as good as it should have been. It might seem to us from this end of history that both those albums, especially Highway 61, were groundbreaking and artistically remarkable but you wouldn't know that judging by the banal comments made about them in the music press. ‘Like a Rolling Stone’, when it was released as a single prior to Highway 61, got some particularly ignorant and fatuous reviews. For some reason, some critics seemed to think there was a string section on it, for instance. Some people were perceptive, though. Some people could see Dylan's new work for what it was, critics like Paul Nelson. Phil Ochs – who wasn’t a critic, he was a fellow folk singer – actually said at the time that it was the greatest album ever made. Of course, that wasn't that difficult to achieve in those days because there’d been relatively few albums made at that point, but there's been a million more made since and I think it's fair to say that Highway 61 is still the greatest album ever made.

ezt: The period between Blonde on Blonde and what became the Basement Tapes was another transition for Dylan, from that of the folkie-turned-rocker into something else entirely. His newest image is one that is still being emulated today: a rock, folk, country blend of introspection, etc. What do people fail to understand about this time in Dylan’s life?

se: The Basement Tapes is a kind of curious interlude because Dylan became a revolutionary by accident. He started recording these quirky songs with his backing band in a basement with musty acoustics and when the rock aristocracy got to hear them because his manager was trying to get cover versions on them it was as though they misconstrued what he was doing as a statement and a counterblast to psychedelia and the studio experimentation that was all the rage at the time. They then started recording their own musty, back-to-basics records. 

You could say that he's sort of gone back to that with the music he's been making since 1997 when Time Out Of Mind came out. There's nothing flash or dynamic about his music now – the instrumentation, I mean – it's all about those sparkling lyrics. It seems to have sealed his reputation, though, because there was a ten year or so period before Time Out Of Mind when he seemed to be creatively spent but now he's sort of settled into this role of grand elder statesman and poet laureate of popular music.

ezt: Dylan’s 1966 accident provided a convenient exit from the pressures of fame. Do you believe he exaggerated its severity as a means of escaping an unsustainable career trajectory, and how did this withdrawal reshape his legend?

se: There seems little doubt that he did exaggerate his injuries and, that being the case, there can only be one reason for that. He became even more of a legend in his absence because in those days celebrities simply didn’t absent themselves from the public sphere on the assumption that if they did the public would forget about them. The pre-internet world, of course, was very different, so he was able to seclude himself without being bothered or exposed and there were actually rumors at the time that he was horribly disfigured or even dead. When he came back with a new album – John Wesley Harding that is, because The Basement Tapes wouldn’t get an official release until 1975 – it was even more keenly received than it would have been otherwise.

ezt: From the underwhelming Nashville Skyline to Self Portrait, Dylan seemed to deliberately undermine his own mystique. Was this self-destruction a form of rebellion against public adulation, or did it reflect a deeper personal crisis?

se: Nashville Skyline was simply a statement that he had other things in his life these days and wanted to concentrate on his own domestic situation rather than the problems of the world. Intertwined with that is almost certainly the desire to get away from the idea that he was the voice of a generation or the conscience of the baby boomers or however else he was perceived. That reached its apex with Self Portrait, which was so bad it was clearly designed to make people go away and stop idolizing him.

ezt: Blood on the Tracks is often hailed as a masterpiece, yet its themes of middle-aged disillusionment may have alienated a younger generation. Do you see this as Dylan’s final break from his countercultural icon status, or simply an unavoidable byproduct of aging?

se: He was simply doing what a lot of artists of his age were doing – exploring his latest situation and, like a lot of people his age, his latest situation happened to be divorce. Of course, not everybody going through that trauma is possessed of his genius and he put together what may be the greatest collection of breakup songs ever written. But yes, it definitely cemented his break from the counterculture or whatever its latest manifestation might be called because rebellion is pretty much the preserve of the young and an album tracing a middle-aged man's divorce is not something that twentysomethings can relate to on a direct basis. He'd moved on and younger people have their own idols closer to their age.

 ezt: Rock journalism wasn’t what it is now when Dylan first came on the scene (or, maybe it can be argued it isn’t what it was after Dylan inspired a deeper read of rock and roll), but how can you describe ways in which Dylan’s music and mythology may have created the height of rock and roll journalism.

se: It would have happened without him, but certainly rock journalism needed to grow up if it were to address songs on Bob Dylan's intellectual plane. You can't write reviews saying, ‘This one is a good one for the dancers’ when you're dealing with something like ‘Like A Rolling Stone’ or ‘Rainy Day Women’. But it's an arresting fact that he released his masterpieces into a world that just wasn't equipped to properly evaluate them. The evaluation has been pretty much retroactive.

ezt: Throughout his career, Dylan has oscillated between reinvention and retreat. Do you believe he has been in full control of his artistic transformations, or has he simply been reacting instinctively to the pressures of fame and history?

se: I think he's a much more calculating and market conscious figure then people have assumed him to be. A lot of people think of him as this gnomic, ascetic figure who’s not the slightest bit interested in market forces or his public image. Having said that I don't think he would have done anything differently in his career, at least in the sixties. He was never concerned back in those days about his sales being jeopardized or about his long-term career because he was very much into his art, even if he always wanted his art to reach as wide an audience as possible.

You can find Egan's book at the usual book-buying places.