Only six years separate the release of Elvis Presley’s first single, ‘Heartbreak Hotel’ — for many the crystalising moment when the forthcoming tide of musical pop culture became clear — and Bob Dylan bursting out of the Greenwich Village folk scene with his self-titled debut. Not long after that release Dylan, much to his own begrudging, was championed the voice of a generation, but unlike many who fall foul of that title he has continued therein to this day. Dylan personally views the tag as unjust and much of his memoir, Bob Dylan: Chronicles One, laments the crushing pressures that being bestowed with it has besieged upon on his life and songwriting.
Seeing as though Chronicles One was published in 2004 and Chronicles Two remains almost mythically elusive, there is no knowing whether he has changed his mind regarding his loathing of his self-perceived misconstrued legacy, and at this stage, it is unlikely we ever will. The unfortunate fact for Bob Dylan is that there has never been a generation in the intervening decades where championing him as a singular voice hasn’t been relevant. In part this is because every single songwriter following his emergence has seemingly been influenced by him in one way or another, there’s scarcely a lyricist out there who wouldn’t tout him as a direct influence.
Much like one of Dylan’s favourite writers Dostoyevsky said regarding the explosion of Russian literature that “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 stirred them up; though the term ‘a soulful singer’ often gets bandied about, he certainly doesn’t possess the vocal skills of someone like 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, God knows what he has reckoned of his worthiness of that accolade in the years since.
In short, he has had a career spanning over half a century and there has not been a single sustained spell within it that hasn’t offered up a plethora of platitude defying wordplay, here we take an impossibly difficult look at highlighting the most outstanding from each outing. It has to be said, however, that it is not a back catalogue exclusively crammed with crème de la crème; Wiggle Wiggle should have been shot at birth, certain songs have swathes of gibberish disguised as nonsense poetry, and lines like “time is a jet plane, it moves too fast” could try harder, but for the most part, Bob resides in a realm you could only call a league of his own.
As a caveat to this list, covers and compilation albums are not included, of course.
A guide to Bob Dylan’s greatest lyrics:
1. Bob Dylan (1962) – ‘Song to Woody’
“Walkin’ a road other men have gone down / I’m seeing your world of people and things / Your paupers and peasants and princes and kings.”
By far and away the easiest choice on this list owing to the fact that his debut only featured two original songs amidst a slew of old folk standards. That being said his early stylings were already in place and it is this particular couplet that brings them to the fore with crisp clarity. Dedicated to one of his many heroes, Woody Guthrie, the line is a perfect mantra for the beatnik generation of which Bob was one of the figureheads. It’s a line that could just as well have come from the novel that started it all, Jack Kerouac’s, On The Road.
2. The Freewheelin’ Bob Dylan (1963) – ‘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”
Only a year on from that debut, at 22-years-old, Dylan was already arriving at one of his most iconic works. One of the greatest and most influential albums of all time, 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.
3. The Times They Are A-Changing (1964) – ‘Boots of Spanish Leather‘
“Oh, but if I had the stars from the darkest night / And the diamonds from the deepest ocean / I’d forsake them all for your sweet kiss / For that’s all I’m wishin’ to be ownin’.”
When he’s not prying at the fabric of society and the human soul, he is busy examining his own. This particular verse delves into that old classic notion of forsaking all for the only thing that matters, but very rarely has it been done so well and so poetically. Many may have imitated it, but few have matched. He drawls it out and it always tugs on the old heartstrings, jarring in its brilliance amidst one of the most influential albums ever.
4. Another Side of Bob Dylan (1964) – ‘To Ramona‘
“The Flowers of the city, / Though breathlike, get deathlike at times.”
Continuing the tradition of working his name into all his early album titles, Bob cooks up another gem in a truly prolific period. This single couplet captures both beauty and the pains of its parting. It’s the sort of line that belongs to Baudelaire or some other such gritty poet, but Dylan was among the first to place this reverential wordplay in song.
Nick Cave, very much a disciple of Dylan, said songwriting is all about putting disparate images together and letting the sparks fly, here Bob creates a bonfire with a simple single couplet that declared a more wistful side to his character.
5. Bringing It All Back Home (1965) – ‘Subterranean Homesick Blues‘
“Don’t steal, don’t lift / Twenty years of schoolin’ / And They put you on the day shift.”
Although Dylan would probably tell you that the best lines from this record are in that verse of ‘It’s Alright Ma’ about the “child’s balloon, the silver spoon, the sun and moon”, but they’re not all that clear to a layman. Whether that simply makes them a cut above the comprehension of the uninitiated masses or the sort of nonsense that led legendary writer Kurt Vonnegut to tout him as “the worst poet alive” back in 1991, is open to interpretation. Nonetheless, it is a clear trait of this particular record to follow a rambling verse with a punchy closing couplet. In one of his best song he almost raps out these lines and it’s this particular duo that hits with the most jarring truth.
6. Highway 61 Revisited (1965) – ‘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?”
All of his previous records had peaked a lot higher in the UK than they had on his star-spangled home soil, but this one rose to number three and, in many ways, it is fitting that it now resides in the music consciousness as one of the quintessential American records. It’s the album where he, for the most part, went full-fledged electric capturing the political and cultural chaos of an America in turmoil and full-blown transition as he did so.
Thus, the couplet has to come from the eponymous tune of the era for that alone (plus we don’t want letters calling us contrarian and all kinds). It’s not just the poetry of the verses in this track, but the vitriol with which he pours them out, you can’t even see them written down without singing them in that famous screech. Choruses may sometimes seem kitsch in the poetical sense and rarely feature on such lists, but — ‘With no direction home’ — alone holds the weight of thousand verses in a gut-punch of pop concision.
7. Blonde on Blonde (1966) – ‘Just Like A Woman‘
“But when we meet again, introduced as friends / please don’t let on that you knew me when / I was hungry and it was your world.”
As is already clear from all the above, Dylan was operating on a different level in the ‘60s. A matter of months after landing the ultimate American record he arrives with not only one of the finest break-up albums but one the very first and perhaps greatest double-album. Not content with the usual 40 odd minutes you could squeeze on to the 12 inches of an LP, he decided to stretch it over two.
Perhaps the highlight is a sweet and simple song of love falling to its end. “Introduced as friends” is a line seeped in poetical realism regarding the torturous business of moving on and relinquishing what once was.
8. John Wesley Harding (1967) – ‘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 fate / So let us stop talkin’ falsely now / The hour’s getting late, hey.”
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. The song is shadowed in biblical overtones, but these two sections of the opening stanza establish a central message. It is a message that usurpers spiritual vapidness and the meaningless of life that pervaded an era of despair in America, in favour of fullness and forgiveness through an attitude of hope of and a sequestering of cynicism that comes from looking for solace beyond the despairing insular world of the watchtower (perhaps a construct for the cross).
No matter which way you view it, the song is a powerful tirade, with some of the most mystified prose put to song. The message may be ambiguous, but the intent is not.
9. Nashville Skyline (1969) – ‘I Threw It All Away’
“Love and only love, it can’t be denied”
A year off represented a lengthy break for Bob by his ‘60s standards. He was worn out, but when he returned it was with one of his best. Nick Cave said if he could have written any song it would be this and that’s good enough to put it on any lyrical list. The message of the song is daringly simple but as the lyrics suggest there’s no denying the truth of it.
10. Self Portrait (1970) – ‘Quinn the Eskimo (Mighty Quinn)‘
“Come all without, come all within / You’ll not seen nothing like the mighty Quinn.”
It was a critical flop that came just as Bob was getting tired of it all. Though the record comprises mostly of covers and strange compositions, this song (perhaps best known by the Manfred Mann version) incredibly managed to be commandeered not only for a Denzel Washington crime-fighting film, but also by Newcastle United fans to sing in praise of striker Mick Quinn, so if it struck enough of a chord with the terraces of St. James’ then it’s good enough to make this list, ultimately because the record offers very slim pickings elsewhere.
11. New Morning (1970) – ‘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.
Even Bob seemed surprised at what he pulled off. These opening lines shine a light on the duality of the turmoil he was facing: the company that came with fame was a bad, but perhaps the loneliness of self-imposed solitude was worse. Though on the surface about a very specific notion that very few have to endure, 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.
12. Planet Waves (1974) – ‘Forever Young‘
“May you climb a ladder to the stars / And climb on every rung / May you stay forever young.”
Recorded with The Band this song was written as a lullaby for his eldest son, Jesse, and it rings with all the simple truth and sentiment of all the lullabies that have survived long enough to be sung to us as children. It is a sweet song from start to finish but this is perhaps its most magical couplet, amidst a record that’s a bit middling by Bob’s standards.
13. Blood on the Tracks (1975) – ‘Idiot Wind‘
“Idiot wind / Blowing every time you move your teeth / You’re an idiot, babe / It’s a wonder that you still know how to breathe.”
With this record, Dylan was back with a bang and he’d hardly been away. The LP also saw a slight changing in writing style. The songs were more so stories regaled rather than predicaments dissected. Amidst all the loveliness on this album, however, is this standout stanza. It is spewed out bile, that proves for all his wonderful sweet touches and poignancy, he’s often at his best when his pen is moved by rage. This particular passage also has humour and a pithiness akin to punk poet John Cooper Clarke. It’s a brutal tirade that any rapper who be happy to host on a diss track.
14. Desire (1976) – ‘Hurricane‘
“In Paterson that’s just the way things go / If you’re black you might as well not show up on the street / ‘Less you want to draw the heat.”
Any art that brings about some real-world justice is worth shouting about. This song was an integral part of the mounting pressure that led to an all-too belated quashing of an innocent man’s sentence after serving almost two decades in jail for a crime he didn’t commit.
The Rolling Thunder Revue period was musically brilliant, but surely the triumph of justice that it helped bring about is the highlight. The lyrics are as detailed as any good piece of reporting, it’s just a travesty that the message they hold still needs repeating.
15. Street-Legal (1978) – ‘Changing of the Guards‘
“Peace will come / With tranquillity and splendour on the wheels of fire / But will offer no reward when her false idols fall.”
It’s a Dylan pop-rock record and it’s certainly not his best. Nonetheless, he was still able to produce these lyrics that moved Patti Smith to tears. Once again, he resorts to that trait of being biblical, but this time it seems rather more personally allegorical rather than mirroring society.
A hidden gem of a tune with some simply soaring lyrics.
16. Slow Train Coming (1979) – ‘Precious Angel‘
“Precious angel, under the sun / How was I to know you’d be the one / To show me I was blinded, to show me I was gone / How weak was the foundation I was standing upon?”
Bob upped the biblical ante on this record much to the surprise of Mark Knopfler who had agreed to assist with the album and remarked to his manager “all these songs are about God!” Though it might have been a bit alienating to have everyone’s favourite voice of a generation refuse to sing any songs that had not been “given to him by the Lord to sing” it still managed to produce some solid lyrics.
With this ethereal little bit of wordplay Dylan proved if the lord really did give him these songs then amidst all the tunes that tread treacherously close to right-wing fundamentalism, he can also write a decent ditty.
17. Saved (1980) – ‘Covenant Woman‘
“I’ve been broken, shattered like an empty cup.”
More of the same from the born-again Christian phase. In truth aside from an abundance of New Testament imagery, there’s precious little to choose from with this outing.
Dylan simply doesn’t have the voice to pull off the gospel stylings and if anything, it all serves to prove that the power of Bob is in his pen, which sadly has a one-way mind here.
18. Shot of Love (1981) – ‘Every Grain of Sand‘
“I gaze into the doorway of temptations angry flame / And every time I pass that way I always hear my name.”
The last of the Christian trilogy. He’s still waxing lyrical about the lord, but this time with stellar poetry, verbose verse and originality. ‘Every Grain of Sand’ has enjoyed a somewhat mixed life. While an early demo existed in 1980, it was first recorded in Los Angeles in 1981 and released not long after as part of the album Shot of Love.
Fast forward a few years though and the track was given two new leases of life when it appeared on the 1991 on Bootleg Series Volumes 1–3 and, a couple of years after that, it was given an airing as part of the 1997 film Another Day in Paradise.
19. Infidels (1983) – ‘Jokerman‘
“Distant ships sailing into the mist / You were born with a snake in both of your fists / while a hurricane was blowing.”
During his more devout years, it would seem he had been stockpiling secular singles because there’s not only a plethora of poetical hits on the album, but many more inexplicably left on the cutting room floor. The beauty of this song, and Bob Dylan’s ‘80s period, is how mad it all is. There’s a complexity to the verses sang over a jingly reggae tune that somehow works and that’s testimony to his rediscovered originality. This list would be incomplete without a bit of perversely daring mayhem.
20. Empire Burlesque (1985) – ‘Clean Cut Kid‘
“They gave him dope to smoke, drinks and pills / A jeep to drive, blood to spill / They said, ‘Congratulations, you got what it takes’ / They sent him back into the rat race without any brakes.”
Continuing in his ‘80s vein of truly awful artwork, that aesthetic bleeds into the record somewhat and it isn’t all that suiting. The lyrics are a little twee and kitsch in places, but the plus side is that it does add some real urgency to certain lines. His first statement on the post-Vietnam fallout saw him recover his searing view on societies flaws that earned him Spokesman status back in the ‘60s. This might not be as erudite as Masters of War, but it’s a stern point made unflinchingly, it’s just a little strange to have it backed by jive.
21. Knocked Out Loaded (1986) – ‘Brownsville Girl‘
“Turn him loose, let him go, let him say he outdrew me fair and square, / I want him to feel what it’s like to every moment face his death.”
Considered by some critics to be Dylan’s worst outing, the highlight was a song co-written with the playwright, screenplay star and actor Sam Shepard (Paris, Texas). The song, ‘Brownsville Girl’, is almost as long as a play at 11:03, but it is an engaging Western tale and lines like this one could easily have come from the thin mouth of Clint Eastwood.
22. Down in the Groove (1988) – ‘Death Is Not The End‘
“And all that you’ve held sacred, / Falls down and does not mend, / Just remember that death is not the end.”
A highly collaborative effort that sadly seems to result in the worst of both worlds rather than a great meeting of minds. Quite frankly if this record was not attributed to one of music’s greatest ever songwriters then it would have probably ended up on the scrapheap.
The above is a nice lyric but it doesn’t quite capture the magic that Dylan’s is capable of.
23. Oh Mercy (1989) – ‘Political World‘
“We live in a political world / Where mercy walks the plank / Life is in mirrors, death disappears / Up the steps into the nearest bank.”
In his scattergun memoir, this is the record Dylan chooses to skip ahead to, not least because it’s his best ’80s album but by all accounts, it’s a success that Bob and producer Daniel Lanois had to scrap towards. This verse embodies the resurrection of his punchy poignancy that always remains relevant and permeates the record both in personal and wider political tales.
24. Under the Red Sky (1990) – ‘Born In Time‘
“In the lonely night / In the blinking stardust of a pale blue light / You’re comin’ thru to me in black and white / When we were made of dreams.”
The record gets off to a frankly atrocious start with Wiggle Wiggle, one of the worst songs ever, but regains some dignity but the wistful opening to ‘Born In Time’.
From the what-were-you-thinking opener, this Byronic poetry restores some faith in the record.
25. Time Out of Mind (1997) – Not Dark Yet
“Well my sense of humanity has gone down the drain / Behind every beautiful thing there’s been some kind of pain.”
Although the ‘80s did offer some good songs, this album was the most ‘Dylan’ that Dylan had been since Blood On The Tracks. Whilst pushing the boundaries and evolving is essential for all artists who want to establish a lasting legacy, sometimes Dylan pushed himself into uncomfortable terrain, with this record he was back on terra firma and standing tall.
It was lines like these, written and performed with simple sincerity, but a trademark depth of craft that made the album soar.
26. Love and Theft (2001) – ‘Bye and Bye‘
“Well the future for me is already a thing of the past / You were my first love / And you will be my last.”
If ‘Time Out of Mind’ hinted at a return to songwriting form, then it was lyrics like these that reaffirmed his godlike status. Songwriters rack their brains for a lifetime to try and rattle something as on the money and straightforward as this loose in its perfect gilded form.
A thousand songs have hinted at this verse but few have delivered it with such concision and unadorned perfection.
27. Modern Times (2006) – ‘Ain’t Talkin’‘
“In the human heart an evil spirit can dwell / I am a-tryin’ to love my neighbour and do good unto others / But oh, mother, things ain’t going well.”
Dylan is not just a crafter of poetical lines, poignant philosophies or political observations, he is most definitely a master storyteller too. ‘Ain’t Talkin’’ is a macabre tale of plague and suffering written like an old folk song collided with a gloomy Camus novel.
Those biblical overtones he loves feature once again but this time adding a devilish twist to an apocalyptic tale. In comparison to some of his work on his Born-Again Christian trilogy, this tune may well prove that Lucifer is simply a better songwriter than the Lord.
28. Together Through Life (2009) – ‘I Feel A Change Comin’ On‘
“Well now what’s the use in dreamin’, / You got better things to do. / Dreams never did work for me anyway, / Even when they did come true.”
It’s not one of Dylan’s best records of recent times but there’s still plenty here for ardent fans to enjoy and just about enough to interest passing visitors, with dark bluesy stylings handled with subtlety and a light touch.
There’s a reticence to these lyrics that leaves them sounding like more of a lament than a lashing of despair, lending the poetry wisdom that elevates it beyond the reach your usual gloomy songsmiths.
29. Tempest (2012) – ‘Pay in Blood‘
“I came to bury, not to raise / I’ll drink my fill and sleep alone / I play in blood but not my own.”
Sometimes it is hard to fathom how Bob Dylan was ever incredulous that the ‘spokesman’ tag was lauded upon him. His songs may be about many things, but on more than one occasion he has spearheaded public opinion in a protest song.
Amidst all the wordplay, allegories and humour of this record is a ferocious outpouring of rage regarding the financial crash around the time of the record. Bankers may have gotten away with it for the most part but there is solace in the fact that they did not escape The Spokesman’s wrath.
30. Rough and Rowdy Ways (2020) – ‘Murder Most Foul‘
“Play, “Love Me Or Leave Me” by the great Bud Powell / Play, “The Blood-stained Banner” play, “Murder Most Foul.”
Whether it has been protestors picketing his property and calling for him to join them in direct action, critical lambasting’s of his born-again Christian phase or playing through pain as his hand recovered from a motorbike accident, it is clear that Bob has braved hardships in his career and his noble battle through them is proof that he did it all for the love of music.
Nowhere is that notion more abundant than on the finale to his latest effort. The album was record-breaking as he became the oldest artist to reach number one in the UK charts with new material, following a career that began seven decades ago. In that time, he has written a plethora of different songs and it is perhaps here where his rebuttal of the ‘spokesman’ tag gains credence, as even the protest songs are ultimately an exercise in the deliverance of music. These seminal last lines hold all his wit and daring to deliver a career-long message of hope and comfort in creativity.