The Contradictions of Dylan: A Primer for the Unconvinced

There is perhaps no figure, in all the popular culture of the modern Western world, who simultaneously combines such dizzyingly high critical esteem with such capacity to bemuse and underwhelm those many, many people who do not connect with him. Bob Dylan is an unassailable musician, and yet to many people – and not people from dramatically divergent cultural backgrounds either, but people who often tick all the other boxes of middle-class good taste – people, in other words, who are expected to like Dylan, who learn that they should like Dylan – his appeal is simply a puzzle. They have resigned themselves to being told all their lives that Dylan is a genius, but they know, through often arduous experience, that he simply will not speak to them. This is not because he is so complex or so challenging that they do not understand him (artists who need to be defended on those grounds are rarely worth the trouble). They understand him just fine. They just fail to see what all the fuss is about.

This article grew out of a long series of emails I sent to a friend of mine who falls into exactly that camp. I sought to explain to him, as best I can, what makes Dylan special to me. This was a uniquely difficult thing to put into words; and I knew that it would be that difficult, because it always has been that difficult. This is the thing about Dylan: for those outside the community of his fanbase – outside the circle of those who get Dylan – it can be extremely hard to understand what the big deal is supposed to be. And believe me, I completely sympathise with that. If you, like my friend, are somebody who has always met Bob Dylan with a shrug, I want to start this piece by telling you that I wholly empathise with your hesitation. Dylan can seem dense, alienating, unapproachable, archaic, or simply just tuneless and monotonous. I hear it. I get the confusion. And it is going to be hard to bridge that gap for you. I was raised with Dylan from age ten, and I learnt very early that articulating why he is special, to people who don’t just feel it on their own, is a uniquely challenging exercise in trying to talk meaningfully about art. Honestly, I still haven’t figured it out. And it’s not just me. Dylan admirers routinely struggle to pin down the essence of what it is about him that speaks to them.

Bear in mind that we’re talking about someone who is effectively universally recognised, among people who are serious about modern music, as one of the three or four most talented, most important musicians since the 1940s. Along with the Beatles, no other artist has had so profound an impact on popular song. That’s as close to an objective truth as it is possible to get in talking about art. Dylan has been called the Shakespeare of modern popular music, and although the Beatles probably fit that analogy slightly better, it still goes a good way to encapsulating his significance. So it’s really, really weird and difficult that he is also someone whose talent and style are so idiosyncratic and peculiar, and also so unappealing for those who can’t get into him, that almost nobody can offer a very true explanation, in words, of why he matters. Those who love him can’t articulate why. Those who don’t, can’t understand.

So are you somebody who has maybe listened to a handful of Dylan songs, but never really got the vibe, or never sunk your time into finding out why he’s so revered? Perfect. What follows is my wholly foolhardy attempt to get you on Dylan’s wavelength. I can’t do that by magically imparting to you the feelings that he inspires in me. I can’t just transfer that response from me to you, so that you become attuned in such a way that you know Dylan’s voice, and you find the hairs standing up on the back of your neck as you grasp just how perfect are his choices of wording, his musical twists, his sharp left turns, his jokes, his punches, his mysterious gestures of ineffability and defiance. But what I can try to do is something rather more prosaic and quantifiable. I am going to take you on a chronological walk through Dylan’s career, dropping recommended songs on you at the crucial moments. Then at least you’ll have a sense of why he matters in historical terms, and you’ll have a few inroads into his music to explore. Will you come out of this a starry-eyed convert? Probably not. But what I hope is that you will at least be able to see – perhaps only in theory, but nonetheless with newfound clarity – what it is that I, that we his fans, can see in him.

Without further ado then, let’s think ourselves back more than half a century, into the quirky, quaint little milieu where Dylan took his first steps as a musician. I am talking about the New York City folk scene, in the early ’60s. Think really old school folk music here. Instrumentally, nothing but an acoustic guitar and voices; lyrically, a roughly equal mix of protest songs and love ballads. Dylan is doing much the same very traditional music as everyone else. He does it arguably the best, which is why he becomes a folk celebrity (if you don’t know “Blowin’ in the Wind,” you should; it’s basically the epitome of this school of music), but it still sounds quite archaic to us now. This is still pre-modern popular music. But, there are already hints that this guy is capable of much more sophisticated work. At this point I suggest you go listen to a song called “Don’t Think Twice, it’s Alright” – his first major break-up song.

To me this is one of his most powerful songs. It’s so understated, but so vicious. This is one of the most brutal break-up songs I know, by anybody, and it’s delivered so quietly and easily – which gives it a whole other level of brutality, because there’s that sense that he’s totally cold to how much pain these words will cause. Dylan is capable of brilliantly stylised disdain and contempt; he can be very genuinely nasty. In this mode, he is nastier than most music (hardcore punk, death metal, etc) that more blatantly sets out to be nasty. It’s breathtaking.

And then, in the mid-’60s, Dylan accelerates at a dizzying pace. Within a handful of years his music grows up and expands into what is easily the most complex, adult songwriting anybody has ever created within the trappings of the popular song. Let me slow down for a moment and talk about that word, “adult”. Here – and it is crucial to be aware of this – is the basic reason why people remember the 1960s as the golden age of popular music. It’s not that the best music in the genre got made in this era (although some of it did, and many people still believe it did). It’s that during the 1960s, popular music stopped being entertainment for teenagers and became an art form for adults. (Yes, entertainment and art are the same thing; yes, teenagers can be just as sophisticated as adults; but run with the stereotypical definitions for a moment in order to get this point.) In the ’60s, the forms of music based in early rock, pop, and folk songs grew up suddenly to become an immensely varied musical genre in which an astonishing array of creative and complex new music was being produced. Popular music exploded in a dozen different directions at once. That’s what made people of that generation feel like no music since that time could possibly top what was happening when they were young.

And the thing is, if you had to point to a single individual who was most responsible for expanding and deepening the field in this way, it was undeniably Dylan. There were a handful of others who did almost as much (Lennon and McCartney at the forefront, obviously), but at least in the early and middle part of the decade, it was Dylan who led the way. He just suddenly started making music that was so much more adult (again, go with the stereotypical meaning) than anything that anybody else was doing. And then, others followed in his wake.

So what was Dylan doing? Well, most obviously, he abandoned folk music and picked up an electric guitar (the famous “going electric” moment). Almost as jarringly for those at the time, and more importantly for the music of the future, Dylan moved beyond traditional songwriting forms and started writing vivid, very personal, very poetic songs that were full of crazy, outlandish imagery – the kind of writing that you might have expected to find in Modernist poetry, but that nobody before him would even have thought of putting in a rock song. Musically, these songs were built on a series of weird experimental twists on traditional blues and rock and pop music forms. Most of it was concentrated on a set of three albums that we now call his “electric trilogy,” released within fourteen months of each other in 1965-66 and now regarded by almost everybody as basically a three-part revolution in songwriting. (Imagine any artist today releasing three first-rate albums within fourteen months. Very few musicians have ever just moved so fast as Dylan could at that time.) To get a sense of how this music felt and sounded, one of the best places you can begin is the very first song on the first album in that trilogy, an album called Bringing it all Back Home. That song bears the sly, evocative title “Subterranean Homesick Blues”.

I love its rapid, dense, tight rhyming scheme. It feels like something you’d chant in the playground, and in the other direction it feels almost like a rap. It feels energised and edgy and grimy, and it bears a lyric that conveys more than many novels. In a way, this kind of barbed social observation piece is the much less straightforward, mutant descendant of the folk protest songs that Dylan started out on. And just as his social comment music was growing much less direct, much more deeply insightful, so too did his more personal songs (although this political/personal distinction essentially becomes redundant around about now). Listen to the confessional-yet-arrogant, sexist-yet-vulnerable “Just Like a Woman”. Observe the way he begins with contempt for this woman, then lets us recognise that he’s compensating for the fact that he showed her his need and his insecurity, and now that makes him uncomfortable so he’s taking it out on her – and yet there is also genuine scorn in there. And observe the way the history between them is implied and never directly stated, but we understand so much about it anyway. Songwriting doesn’t get much more masterful than this.

I’m deliberately keeping the number of actual songs I’m giving you at a minimum here, oh my Dylan-sceptical reader. I’m aiming to give you an orientation within which you can then go listen to more of his stuff, if you want to.

Late in 1966, Dylan was in a serious motorcycle accident. This brought his great, scene-changing creative streak to an end. Dylan had a fifty-year career still ahead of him, but never again would he be out on the cutting edge in the same way. I actually prefer a lot of his post-crash music – if you took away everything he made before the crash, Dylan would still have a richer and more wonderful catalogue of work than most other songwriters – but none of it is historically vital in the same way. A good sample from the immediate post-crash period is “All Along the Watchtower,” which neatly illustrates the way he has, superficially speaking, “retreated” to a simpler musical form, an acoustic folk song – but in fact, there is actually a huge amount going on here, strung through this song’s elegant matrix of mythic symbolism and literary allusions. This is characteristic of the next fifty years of Dylan: seemingly less bold and less innovative musical forms, but profoundly sophisticated and powerful songwriting performed within those traditional structures.

And that, to get down to the crux of it, is actually a big part of the secret of his appeal: traditional forms of music that can tap directly into us on a very basic level, but paired with songwriting that might feel traditional, but is actually very modern and very layered. Here’s another example: in the 21st century, Dylan has had a big creative resurgence, and it’s founded in a series of albums of old-style, early-20th-century blues. Old-fashioned blues, played well, is among the most characterful music I know – you can’t deny, the blues just has personality – but I still get bored of it quickly under most circumstances. It’s simply not my music. But that said, I love Dylan’s work in the blues, because he makes it both musically and lyrically so compelling. Go listen to “Thunder on the Mountain”. You can’t point to any specific thing about this song that actually would have been out of place in the 1940s (okay, apart from that reference to Alicia Keys). But taken as a whole, the song would have been completely out of place in the 1940s, because it simply feels so utterly contemporary. This kind of indefinable alchemy is part of what makes Dylan so special.

And that, class, is where I will bring this necessarily brief survey to a close. Discounting “Blowin’ in the Wind,” which I know I mentioned only tangentially, I’ve pointed you to just five select songs to give you a sample of Dylan’s richness and variety. I shan’t hope to have fired every reader of this piece with my own enthusiasm for this often baffling, sometimes unfathomable, but almost always compelling songwriter. But I hope it has given you at least an approximation of an awareness of why Dylan matters, and why those of us who love him find his music so meaningful. This is me signing off, ready to go listen to The Basement Tapes yet one more time.

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