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A journey through Bob Dylan’s songwriting in 10 of his greatest lyrics

Only eight years separate the release of Elvis Presley’s debut single, ‘That’s All Right’ in 1954, considered by many to be the birth of pop culture, and the release of Bob Dylan’s self-titled debut in 1962. From that moment on, the 20-year-old troubadour from Hibbing, Minnesota, began moulding the future of popular arts. 

Now, over half a century later, he is still producing masterpieces, and with each passing one, his influence on the industry has been felt. In short, we can all be glad that he was able to use his Promethean force to wrestle music culture towards an entirely new and interesting direction, and even more blessed that barring the occasional blemish, he has continued in that driving vein since.

Nowhere has his cultural signposting been clearer than with his lyrical content. When others were writing about heavy petting and dancefloor-based courtships or rehashing folk songs as old as time, Dylan propagated societal reflections and introspective poetry like no other. It would seem that every single songwriter following his emergence has seemingly been influenced by him in one way or another. In fact, there’s scarcely a lyricist out there who wouldn’t tout him as a direct influence.

Much like one of Dylan’s favourite writers, Fyodor Dostoyevsky said regarding the explosion of Russian literature: “We all came out of Gogol’s Overcoat”, it would seem that every reverential songwriter after 1962 crawled out from Dylan’s cambric shirt. And it is very much his ‘writing’ that has had them clinging to his gingham coattails forevermore. 

Although the term ‘a soulful singer’ often gets bandied about, he certainly doesn’t possess the vocal skills of someone like Nina Simone, and though his guitar plucking may well be prodigious it pales in comparison to some of the true greats of the six-string, but his writing is near incomparable. His skill even earned him a Noble Prize for Literature in 2016. 

While his songwriting analytic obscure quality of depth and diversity, every artist displays certain patterns to their work, and we’re going to try to weave our way through them. Although Dylan himself would probably tell you, as he has said in the past, that his best line is, “Darkness at the break of noon/Shadows even the silver spoon/The handmade blade, the child’s balloon/Eclipses both the sun and moon,” but for those outside of the folk phenoms own mind, it seems the sort of obfuscated line that prompted the late novelist Kurt Vonnegut to remark: “[He] is worst poet alive. He can get maybe one good line in a song, and the rest is gibberish.” 

Below, we have hand-plucked not only his most gilded poetic gems, but the ones that define him best as a songwriter in his glinting career. 

Bob Dylan’s best lyrics:

Hold no punches: ‘Masters of War’

 “And I hope that you die 
And your death will come soon
I’ll follow your casket
By the pale afternoon
And I’ll watch as you’re lowered
Down to your deathbed
And I’ll stand over your grave
’Til I’m sure that you’re dead.”

Naturally, a song titled ‘Masters of War’ was never going to be a tale of sunshine and rainbows. With Dwight D. Eisenhower’s farewell message of guarding against “the acquisition of unwarranted influence… by the military-industrial complex” still ringing in the air, the song was always set to be a million miles from some sanguine songsmiths hopeful rally cry, but when this final verse lands the bluntest bludgeon in the history of music, it almost shakes the needle off the groove. People caution that hate is a strong word, but clearly, it’s not strong enough for Bob and he still stops you in stone dead with the no-punches-pulled verse to this day. 

“I hope that you die,” is a line that will simply always cut, and Dylan spits it out with as much caustic rage as he can muster. The lyric is neither screamed nor hysterical, it’s just a thing of unflinching fury that lands with the sound of a bowling ball being dropped on the porcelain heads of power. He’s rightfully indignant about warmongering bastards, but at just 21 years old when he wrote this song in the winter of 1962/63, it singled him out as a truly brave incendiary presence in the music industry and one who would need a cholinic if he gave any less of a shit.

Playfulness: ‘Talkin’ World War III Blues’

Half of the people can be part right all of the time
Some of the people can be all right part of the time
But all of the people can’t be all right all of the time
I think Abraham Lincoln said that ‘I’ll let you be in my dreams if I can be in yours’
I said that

It seems timely to follow up ‘Masters of War’ with a trait that dispels the often wrongly held notion that Dylan’s lyrical diction is one of all work and no play. Contrary to his political and spiritual overtures, his lyrics are often playful and humorous.

Only a year on from that debut, at 22-years-old, Dylan was already arriving at one of his most iconic works with The Freewheelin’ Bob Dylan. It is one of the greatest and most influential albums of all time, on which nearly every song is now the sort of classic folk standard that he covered on his first record. Although ‘Talkin’ World War III Blues’ might not be one of the best of the best on the album, this gem of a closing verse and its unique delivery sets out the iconoclastic styling that would champion him the voice of a generation and leave the rest us wondering how he could ever be so bewildered by it – nobody was writing like this in 1963. 

Guy Garvey of Elbow has since described the verse as one of the greatest closers in music and that’s good enough to vindicate its place on this list. 

Pure poetry: ‘To Ramona’

The pangs of your sadness / Will pass as your senses will rise / For the flowers of the city though breathlike, get deathlike sometimes.

Nick Cave once said that songwriting is all about counterpoint. “Counterpoint is. the key,” he explained, “Putting two disparate images beside each other and seeing which way the sparks fly.” With this perfectly exacting point of contrast in ‘To Ramona’, Dylan captures both beauty and the pains of its parting. 

It’s the sort of line that belongs to Charles Baudelaire or some other such gritty poet, but Dylan was among the first to place this reverential wordplay in song. With it, he doesn’t just cause sparks to fly, but whisks up a bonfire of imagery and reveals a more wistful side to his character. 

Stick the boot in: ‘Positively 4th Street’

“I wish that for just one time you could stand inside my shoes 
And just for that one moment I could be you 
Yes, I wish that for just one time you could stand inside my shoes 
You’d know what a drag it is to see you.”

Perhaps one of the greatest songs ever written without an album to call home, the history of the track seems to back up the point that this is Dylan unloading something off of his chest. If there is a better break-up middle finger in music than the lambasting that Dylan offers up on ‘Positively 4th Street’, then it needs to make itself known.

This verse is a searing attack that diminishes even the casual listener to a boot quaking hot second, so lord knows what Edie Sedgewick (who it is thought to be about) felt when she heard it. And the beautiful paradox of it all is that rarely has such unabated disdain existed with such a sweet jangling melody, providing the notion that he’s not even mad, he’s just sorely, sorely disappointed. 

Sum it up in the chorus: ‘Like A Rolling Stone’

“How does it feel
How does it feel
To be on your own
With no direction home
Like a complete unknown
Like a rolling stone?”

Choruses rarely feature in greatest lyric lists, usually because they are the moment when poetry of great depth is sequestered out of necessity for a singalong refrain. Dylan, however, often uses them quite differently and it is a sign of his mastery that they remain catchy all the same. Quite often his choruses are summations of what the verses are getting at.

In ‘Like a Rolling Stone’ wrath and rage have rarely met with such poignancy. Although ostensibly the target was his ex-girlfriend Edie Sedgwick, who departed from high society to be part of the art scene but sadly stepped one toke over the line into the darker side of counterculture, there is a hint of higher power saying there is liberation in the fact you now having nothing to lose. 

If Dylan was the Jesus figure of the counterculture movement, then this was his moment of caustic condemnation in the temple of his own creation, and it proved one thing beyond doubt: hell hath no fury like Dylan scorned.

Literary prose in song: ‘Visions of Johanna’

“But she just makes it all too concise and too clear
That Johanna’s not here
The ghost of ‘lectricity howls in the bones of her face
Where these visions of Johanna have now taken my place.”

There is no doubting that Dylan’s songwriting is utterly unique. There are very few songwriters where you could see their work written down and without having heard the song, have a guess at who penned it. One of the revealing factors when looking at an unknown Dylan piece would be the very singular signifier that nobody writes quite as close to literary prose as Dylan. 

For starters, ‘Visions of Johanna’ has a word count pushing 500, and yet his understanding of rhythm and melody means he can pour them all out without breaking a steady flow. This handy knack means he can utter evocative metaphors like “the ghost of ‘lectricity howls in the bones of her face” with the ease of blackbirds endless chorus of half notes. 

Daring simplicity: ‘I Threw It All Away’

“Love and only love, it can’t be denied.”

In an era that found Dylan crooning with a silky voice that seemed to have power blasted off the old “sand and glue”, he crafted a song suitably sweet to go along with it. However, it was also such an unadorned dose of unarguable profundity that it was sweet but never saccharine, like some sort of spiritual honey. 

Although the melody may be dainty the message is anything but: in an almost daringly simple way Dylan croons out “love and only love,” in a bold entreaty of harmony. This defiant mantra emboldens the melody with a monolithic sense of spiritualism. Subtlety is overrated, as any carpenter and they’ll tell you that the nail sits most flush when it’s been bashed right on the head. 

Biblical overtones: ‘All Along the Watchtower’

“There must be some kind of way outta here, Said the joker to the thief […] No reason to get excited, the thief, he kindly spoke, There are many here among us, Who feel that life is but a joke,

But, uh, but you and I, we’ve been through that, And this is not our fat, So let us stop talkin’ falsely now, The hour’s getting late, hey.”

The deep introspective spiritualism of Dylan’s oeuvre is often shadowed in biblical overtones. They’re many ways to interpret this song but if my opinion is worth a dime, it seems to be about Christ upon the cross and the two thief’s conversing on either side. I could be wrong, but it proves an important point regardless: it is the ambiguity and philosophical scope of such songs that makes them stand out as masterpieces in the world of modern music. 

With ‘All Along the Watchtower’ he provided a message that usurped spiritual vapidness and despondent nihilism that pervaded an era of despair in America. In favour, he presented a note of fullness and forgiveness through an attitude of hope and the joyous conquest over cynicism that comes from looking for solace beyond the despairing insular world of the watchtower.

Deeply personal: ‘Sign on the Window’

“Sign in the window says ‘lonely’, Sign on the door said ‘no company allowed.’”

Perhaps the quality of these lyrics is revealed with a bit more context; 1970 represented a time when Bob was truly despairing of fame and the cursed ‘Voice of a Generation’ tagline. For the album, he intentionally stripped his songs of anything that could be interpreted as some sort of satirical metaphor, and surprisingly such constraints resulted in somewhat of a masterpiece.

The song shines a light on the duality of the turmoil Dylan was facing at the time of writing it: the company that came with fame was bad, but the loneliness of self-imposed solitude was worse. Though on the surface this a very specific notion, in a spiritual sense, loneliness versus the fear of taking the first steps against it is a battle that resonates with a far greater universality.  

Societal perceptiveness: ‘It’s Alright, Ma (I’m Only Bleeding)’

“Disillusioned words like bullets bark 
As human gods aim for their mark
Make everything from toy guns that spark
To flesh-coloured Christs that glow in the dark
Easy to see without looking too far
That not much is really sacred.”

Even when the personal element of his lyrics is removed, and the target of his scorn is something as nebulous as the consumer culture that sells vapid Christian iconography out of the front door and shifts bullets out the back, the scratches can still be felt. The whole song is an unfurling barrage of societies contradictions and a slander of the puppets that parade around it. 

While some verses might be too cryptic for Kurt Vonnegut’s taste this one, however, lands on the nose and bloodies it. “Not much is really sacred,” is the surmise of the entire song and it slips out with the same casual hatred as the rest of the verses. Dylan might have loathed being tagged as the voice of a generation, but he also acknowledges that he had “power and dominion over the spirits. I had it once and once was enough.”