In the late 1990s David Bowie bemoaned the grand mausoleum of music open to Bob Dylan to pluck his setlists from. Bowie declared that he was “green with envy when [he] heard Bob Dylan’s got about 140 songs he can choose from.” I can assure the late Starman that he wouldn’t be quite so envious if he had to delve into that monolithic back catalogue and emerge clutching only 20 gems from the multitude of masterpieces contained therein. And moreover, vie against a co-worker in the thankless task of ranking them.
However, with more than a hint that such a heavy-handed treatment of such delicately filigreed artworks might not be befitting, we persevered for the sake of interesting discussion and the chance to eulogise perhaps the greatest living songwriter of all time. With added emphasis on the word ‘perhaps’ because we don’t want to make this simple hero-worshipping piece any more divisive than it most likely already is.
Whilst the word mausoleum has already been bandied around a few times in this introduction, Dylan’s back catalogue is also somewhat of an odditorium. Whilst the aforementioned David Bowie might seem like a disparate comparison on the surface, they share a commonality when it comes to a chameleonic songwriting style. They both adhere to the same ethos of “never play to the gallery,” and it could be argued that Dylan even invented this form of creative iconoclasm.
It is an indeterminate ‘I’ll go my way, you go yours’ attitude to songwriting that has admittedly thrown up some tracks like ‘Wiggle Wiggle’ that should have been shot at birth and perhaps our ranking hints that he is at his very best when spewing words over an acoustic. Still, the kaleidoscopic beauty of buttressing brilliantly berserk songs like ‘Jokerman’ with two chords and the perfunctory presence of a simple heartfelt soul is what has made his 59-year music career so beautiful.
In short, Bob Dylan was there at the birth of pop culture, and we can all be glad that he was able to use his Promethean force to wrestle it towards an entirely new and interesting direction. Much like one of Dylan’s favourite writers, Fydor Dostoyevsky, once said about 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.
Now, over half a century later, he is still producing masterpieces. Below we have jostled and butted heads in a bid to bring you 20 of his very greatest, despite the fact the list could be doubled, triple and quadruple without much degradation to the quality of songs at hand. What’s more we’ve ranked them to give your eyes a chance to adjust to the gleaming gems fusioned from the ether into folk-perfected existence. Without further ado let’s get into his top 20.
Bob Dylan’s 20 greatest songs of all time:
20. ‘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.
In 2020 as he approached his 80th year, he turned in yet another masterpiece. ‘Murder Most Foul’ was an embodiment of his entire career, from his profound sense of place within society, to the simple deliverance of music, and lastly his absolute love of the art. The seminal last line to this song – “Play, “The Blood-stained Banner” play, “Murder Most Foul.” – contains all his wit and daring to deliver a career-long message of hope and comfort in creativity.
19. ‘Tangled Up In Blue’
A part of arguably Dylan’s greatest album, Blood on the Tracks, ‘Tangled Up In Blue’ represents one of Dylan’s most enterprising moments, all the while maintaining his notorious drawl. Though the singer had always been open about his feelings, allowing his music to do most of the diarising needed to succeed in the pop world, this track is one of his most open.
Not because it accurately depicts the ending of a doomed relationship, though it does that with the sweetest efficiency, but because he portrays them in a veracious and voicefrous way — through fragmented vignettes. The kind that usually only arrive after the event, but for Dylan’s artistic eye, appeared within a moment’s notice. It provides grounding to one of the singer’s finest efforts.
18. ‘The Man In Me’
After a decade of musical dominance in the 1960s, Dylan found himself retreating from the accursed ‘voice of a generation’ tag that bestowed upon him. For his 1970 album, New Morning, 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 Man in Me’ stands out in the party of Dylan’s back catalogue as a chilled-out presence sipping on a White Russian. If the song was any more laidback, he’d have to play it lying down and he invites you along to bask in this sonic balm. It is a dreamy piece of music, ideal for bathtub escapism (just make sure there aren’t any marmots about).
17. ‘All Along the Watchtower’
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 sequestering of cynicism that comes from looking for solace beyond the despairing insular world of the watchtower.
16. ‘Sign On The Window’
Perhaps ‘Sign on the Window’ is an inclusion that may raise some eyebrows and perhaps I’ll Google will toss this old article back to me and I’ll second guess the inclusion. However, one of the most beautiful things music can do is transfigure itself to a higher level even after a myriad of listens.
Within the depths of lockdown this track moseyed up and warmly declared itself to me as one of the most underrated in Dylan’s back catalogue and I wholeheartedly agreed. 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.
15. ‘Idiot Wind’
With Blood on the Tracks Dylan was back to narrative songwriting with a bang. The songs were more so stories regaled rather than predicaments dissected, and ‘Idiot Wind’ is a ferocious tale of rock ‘n’ roll.
The song 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. There are couplets with humour and mirthful scorn akin the pithiness of the eponymous punk poet John Cooper Clarke. It’s a brutal tirade that any rapper who be happy to host on a diss track, all housed in a rolling earworm of a melody to boot.
14. ‘Lay Lady Lay
Nashville Skyline, the album that features the incredible track ‘Lay Lady Lay’ was a huge departure for Dylan. True, he had ditched folk a long time ago but now it seemed he was also ditching the voice of a generation too. The singer puts on his best croon to bring the album to life and there is perhaps no better showing of this than on ‘Lay Lady Lay’.
Detractors may call this song out for being a little on the cheesy side. After all, what’s rock and roll about pledging to be a dutiful husband? But, in a catalogue of songs that preached about the absurd beauty of love and the heroic nature of war among countless other themes, it feels fitting that at least one of his songs should be about devotion.
13. ‘It’s All Over Now, Baby Blue’
1965’s Bringing It All Back Home is one album that few musicians worth their salt would disagree over. Positively packed with reminders of Dylan’s unfathomable and unfiltered talent, ‘It’s All Over Now, Baby Blue’ has gone on to typify this moment of artistic purity for Dylan. It’s another track that puts Dylan in the centre of a pool of petrol, only to sing: “Strike another match, go start anew”.
In typical Dylan fashion, we are unsure whether he was directing his self-help memos of moving to a burned lover or indeed the fans who were still vying for his folkie blood. The truth is, like all great Dylan songs, it really doesn’t matter. Lyrically robust without feeling flagrantly indulgent, the song remains a cherished piece of his unwavering canon.
12. ‘I Threw It All Away’
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 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. Nick Cave said if he could have written any song it would be this and that’s a good enough calling card to earn its place on any list.
11. ‘Subterranean Homesick Blues’
To open his electric oeuvre on Bring It All Back Home Dylan met his “Judas!” picketers with a fist. Rather than clutch to the safety of a successful formula, Dylan laced this proto-rap song with a flourish of jostling acoustic and electric guitars.
The song is a visceral bludgeon and an incendiary attack on orthodoxy in all its guises. However, what really makes it a masterpiece is that it thrashes about like a mule, kicks the naysayers into touch, and makes them look like Amish arbiters of music in two minutes and twenty-one seconds flat. It has one of the greatest music videos of all time as an added extra, just to ram home that Dylan was rattling culture about like a floating butterfly and a stinging bumblebee in this period.
10. ‘A Hard Rain’s A-Gonna Fall’
The saying goes, “hell hath no fury like a woman scorned,” but perhaps they have never witnessed Bob Dylan penning a song about the ensuing Cuban Missile Crisis. An onlooker who was there when the songwriter began working away at the fantastic ‘A Hard Rain’s A-Gonna Fall’ said the song, “roared right out the typewriter”.
Full to the brim with apocalyptic imagery and the kind of lyricism that only Dylan could muster, the song was recorded in one take and hasn’t spent much time out of the studio since. Covered endlessly, the song remains a vibrant piece of anyone’s set, let alone the man who spawned it.
9. ‘It’s Alright Ma, (I’m Only Bleeding)’
Few songs announce Bob Dylan as quite possibly the most gifted lyricist of all time more succinctly than ‘It’s Alright Ma, I’m Only Bleeding’. Containing one of Dylan’s most prophetic and poetic lines: “He not busy being born is busy dying”, the song ranks as one of the greatest on this alone.
When you add into the mix the body shaking vitriol of the rest of the song and you have a heady cocktail capable of rendering an elephant unconscious. The basic premise of the song is not to trust your establishment, something that Dylan maintains to this day. It was this sentiment that makes the songwriter one of the most widely accredited around.
8. ‘Mr Tambourine Man’
Of course, no list would be complete without one of Dylan’s most famous songs, ‘Mr. Tambourine Man’. Though it would take The Byrds in the sixties and Micherlle Pfeiffer in Dangerous Minds in the nineties, to bring the track the acclaim it deserves, the only aficionados complaining about the songs inclusion in our list are bonafide snobs. The song, assessed separately from Dylan’s mystique stands up to anything else released in the decade.
Wrongly pinned down as a “drug” song by many, the track is more accurately seen as a moment of reflection of writing itself. Built out of moving imagery and non-contexual vignettes, the track does carry similar nuances to the actual feeling of being a little spaced out, but that’s the exact same effect as the best poetry has too.
7. ‘Just Like A Woman’
Penning the ballad on Thanksgiving, Dylan provided the music world with another blueprint for success. The song has been continuously covered ever since it was released on 1966’s Blonde on Blonde with Joe Cocker providing perhaps the nearest to competitor to Dylan’s original. Allegedly written for Dylan’s muse, Edie Sedgewick, the song is a romantic moment in the songwriter’s visceral canon.
It’s a departure for Dylan too. The song is far more romantic than his usual output and is certainly toying with the indulgent saccharine style that soe many pop singers fell victim of. But, what Dylan always possessed was his scything tongue. Singing “she breaks just like a little girl,” was one sharp moment in the track and hinted that even at his most loving, Dylan’s wit was whip smart.
6. ‘Positively 4th Street’
If there is a better break-up middle finger in music than the lambasting that Dylan offers up in ‘Positively 4thStreet’ then it needs to make itself known. For the last verse Dylan penned the absolute searing dirge of, “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,” and it crowned this folk-rock perfection king, and who’s asking?
The song itself is the twin brother of ‘Like A Rolling Stone’. It packs all the same punch and caustic acerbic wit, riding along on a slightly sweeter organ tone. It jangles in along on a soaring syncopated melody and beneath it all is a wondrous vivified indifference.
5. ‘Don’t Think Twice, It’s Alright’
The sheer number of singer-songwriters who have had a go at ‘Don’t Think Twice, It’s Alright’ is a testimony to its brilliance. Where most break-up songs are straightforward laments, Dylan captures duality and complexities with a song akin to postmodernist prose, that leaves you questioning the narrator and protagonist in equal measure.
All that being said, with this song Dylan unquestionably arrives at one of his finest melodies to boot. The plucking is very much in his key, and the solemnity dwells in the wheelhouse of his soul. Many might have had a go at it, but this track is a distillation of Dylan in a very pure form and as such it has never been bettered.
4. ‘It Ain’t Me Babe’
By 1964, Bob Dylan was already considered a folk legend after making a name for himself in the underground Greenwich Village club scene and catapulting into stardom with his first three albums. But with his fourth studio release, Another Side of Bob Dylan, Dylan began to shy away from political ballads in favour of more personal songs about the human experience, which is evident in ‘It Ain’t Me, Babe.’
Although in true Dylan fashion, the song’s meaning has never been explicitly revealed, biographers and fans generally agree the inspiration comes from his 1963 visit to Italy to search for his girlfriend at the time Suze Rotolo, who was studying there. The song, along with the album in its entirety, was recorded on June 9, 1964, in a single all-night studio session, supplemented by “a couple of bottles of Beaujolais”.
It’s a song that certainly has its detractors but they are only likely gathered because of the song’s immense popularity. Covered endlessly by some of music’s heroes, the track remains one of the most potent visions of Dylan’s ability to transcend genre and culture and provide a defining anthem.
3. ‘Hurricane’
The track, a protest song written by Dylan alongside Jacques Levy, details the imprisonment of middleweight boxer Rubin “Hurricane” Carter. In the song, Dylan sings about the acts of racism against Carter and the subsequent false trial and conviction — it is pulsating with intent and purpose.
Convicted twice of a triple murder, Carter served almost 20 years in prison until he was released after a judge subsequently granted a petition of habeas corpus on procedural grounds in 1985. While in prison, Carter was visited by Dylan and was inspired to write his autobiography in which he maintained his innocence. After their meeting in Rahway State Prison in Woodbridge Township, New Jersey, Dylan was inspired to write his song about Hurricane but initially struggled to put his emotions onto paper when the time arrived.
“Bob wasn’t sure that he could write a song [about Carter]… He was just filled with all these feelings about Hurricane,” Levy detailed about Dylan’s approach to the song. “He couldn’t make the first step. I think the first step was putting the song in a total storytelling mode. I don’t remember whose idea it was to do that. But really, the beginning of the song is like stage directions, like what you would read in a script: ‘Pistol shots ring out in a barroom night… Here comes the story of the Hurricane.’ Boom! Titles.”
It’s a song that bleeds authenticity all over the airwaves, propelling Dylan into a realm of storytelling that only Aesop can access.
2. ‘Blowin’ in the Wind’
Few songs can reach the level of mythology that ‘Blowin’ in the Wind’ has. Closer now to theological text than perhaps any pop song has ever been, ‘Blowin’ in the Wind’ now works as a mantra for allowing the troubles of life to flow through you as a breeze passes through cotton. The song may have been written in a matter of minutes, but it still lands squarely on the ground as one of Dylan’s timeless masterpieces.
Sure, if we want to be picky we could refer back to countless other Dylan songs as having perhaps the same artistic value as this one. After all, can the best art be created in seconds rather than hours? But to dismiss the decades-long cultural impact of a song like this would be to refuse to see the whole picture.
The truth is, unlike any other Dylan song, this one has transcended everything we know about rock music. It doesn’t demand attention, it assimilates itself into our environment seamlessly, it doesn’t hang itself on a hook, despite the chorus being one of the most well know around, and it certainly doesn’t need bravado to sell it. The beauty of this song is the same beauty that can be found in the smell of rain, the warmth of the sun and the, yep, you guessed, cool air of the wind. This song, above all else, is the very nature of why we love music — it gives so much more than it takes.
1. ‘Like A Rolling Stone’
An article of this sort really rams home the subjectivity of music. It is a realm with few concrete truths and anything is up for grabs in its rambling undefined discourse. However, every now and again, there is a song that presents itself with such unflinching brilliance and mercurial bravura that every living thing under the sun just has to stand back and regard it. You might not think it’s his best, but any musician, fan or inclined person worth their salt would have that this song is on to something. Dylan loathers, lovers, and indifferentists alike all find something in this track and for that alone it stands out from the subjective stream of music with unapologetic individualism.
Wrath and rage has rarely met with such poignancy, and by the good grace of Dylan and whatever mystic figures of folk fate were weaving his back catalogue in this period, it’s all embalmed in an adrenalised sonic fuzz that figuratively slaps anyone half-listening into captivated submission.
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. This song is a masterpiece and it has no problem telling that to anyone who’ll listen and even those with their backs turned can get caught up in its glorious maelstrom too.
