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Bob Dylan at 80: Exploring his 80 greatest songs to date

“I think a hero is who understands the degree of responsibility that comes with his freedom.” – Bob Dylan. 

For six decades now, Bob Dylan has presided over the cultural landscape of music like a rambling Greenwich Village spawned numen, wayfaring a serpentine path through divine creative pastures and leaving a breadcrumb trail that has shaped the world in his wake. 

From his paid gig at Gerde’s Folk City where a sign was mocked up calling him the “Son of Jack Elliott”, all the way up to ‘Murder Most Foul’ which Nick Cave described as sounding as though “it has travelled a great distance, through stretches of time, full of an earned integrity and stature that soothes in the way of a lullaby, a chant, or a prayer,” Dylan his simultaneously been a timeless connection to the past while illuminating the future. 

There is no doubting that throughout his career there have been peaks and troughs, ‘Wiggle Wiggle’ for instance, is a song that should’ve been shot at birth. However, these lows are the best sort of lows because they have been acquired through the same means as the highs – a daring artistic integrity that refuses to yield to any influence other than his own unfettered muse. He is a songwriter who has cast his line into the stream of floating ether and sometimes he has pulled up an old shoe fit for the ash heap, other times there just haven’t been any fish, but more often than not he has proved himself capable of hauling up great white whales that have benevolently changed music forevermore. 

This has resulted in such a grand mausoleum of song that in the 1990s David Bowie bemoaned the amount of choice he had for a setlist in comparison to Dylan, “I was green with envy,” he said, “When I heard Bob Dylan’s got about 140 songs to choose from.” It is a predicament that has meant that even plucking these 80 songs is not an easy task. Such is the measure of his profuse brilliance that many of the greatest artists of all time have found themselves looking up at his tower of work and marvelling in admiration, amazement and envy. 

The other reason that David Bowie quote is pertinent is because that whilst they might seem like disparate artists 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. When he plugged in and faced a barrage of Judas chants, he exhibited a devil-may-care punk attitude aeons beyond his years and well ahead of its time.

With this profound sense of freedom to freely muse and snatch a semblance of beauty and understanding from anywhere and everywhere, he has inspired generations of songwriters, and as Dylan said himself what can be greater than that: “The highest purpose of art is to inspire. What else can you do? What else can you do for anyone but inspire them?”

This notion has been ratified by near enough every artist to follow in the path of his illuminating introspection, from Paul McCartney who said that when he met him, “I could feel myself climbing a spiral walkway as I was talking to Dylan. I felt like I was figuring it all out, the meaning of life” to the current generation of songwriters like Johnny Flynn who once stated: “Bob Dylan has and Einstein had their own way of perceiving the universe and translating it for us.”

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.

Below, we have compiled a collection of his 80 greatest songs chronicling his career to date. From his derivative but nonetheless, heartfelt debut consisting mainly of covers, to the shackle-shed wisdom of last years ‘Rough and Rowdy Ways’, there are songs worthy of entry from every generation during a career in which Dylan has tossed out masterpieces like a bird taking to flight all while living by the mantra of “All I can do is be me, whoever that is.”

Enjoy the full playlist, below.

Bob Dylan’s 80 greatest songs:

  • ‘A Hard Rain’s A-Gonna Fall’
  • ‘Abandoned Love’
  • ‘All Along The Watchtower’
  • ‘Ballad of a Thin Man’
  • ‘Blind Willie McTell’
  • ‘Blowin’ in the Wind’
  • ‘Bob Dylan’s Dream’
  • ‘Boots of Spanish Leather’
  • ‘Brownsville Girl’
  • ‘Buckets of Rain’
  • ‘Changing of the Guards’
  • ‘Chimes of Freedom’
  • ‘Clean Cut Kid’
  • ‘Day of the Locusts’
  • ‘Desolation Row’
  • ‘Dignity’
  • ‘Don’t Think Twice, It’s All Right’
  • ‘Every Grain of Sand’
  • ‘False Prophet’
  • ‘Forever Young’
  • ‘Gates of Eden’
  • ‘Girl from the North Country’
  • ‘Gotta Serve Somebody’
  • ‘Highway 61 Revisited’
  • ‘Hurricane’
  • ‘I Contain Multitudes’
  • ‘I Dreamed I Saw St. Augustine’
  • ‘I Shall Be Released’
  • ‘I Threw It All Away’
  • ‘I Want You’
  • ‘Idiot Wind’
  • ‘If Not for You’
  • ‘If You See Her, Say Hello’
  • ‘Isis’
  • ‘It Ain’t Me Babe’
  • ‘It’s All Over Now, Baby Blue’
  • ‘It’s Alright Ma (I’m Only Bleeding)’
  • ‘John Wesley Harding’
  • ‘Jokerman’
  • ‘Just Like A Woman’
  • ‘Just Like Tom Thumb’s Blues’
  • ‘Knockin’ On Heaven’s Door’
  • ‘Lay, Lady, Lay’
  • ‘Like a Rolling Stone’
  • ‘Love Minus Zero’
  • ‘Maggie’s Farm’
  • ‘Make You Feel My Love’
  • ‘Man of Constant Sorrow’
  • ‘Masters of War’
  • ‘Most of the Time’
  • ‘Mr. Tambourine Man’
  • ‘Murder Most Foul’
  • ‘Not Dark Yet’
  • ‘One More Night’
  • ‘One of Us Must Know (Sooner or Later)’
  • ‘One Too Many Mornings’
  • ‘Political World’
  • ‘Positively 4th Street’
  • ‘Rainy Day Women #12 & #35’
  • ‘Ring Them Bells’
  • ‘Sad-Eyed Lady of the Lowlands’
  • ‘Shelter from the Storm’
  • ‘Sign on the Window’
  • ‘Simple Twist of Fate’
  • ‘Slow Train’
  • ‘Stuck Inside of Mobile with the Memphis Blues Again’
  • ‘Subterranean Homesick Blues’
  • ‘Talkin’ World War III Blues’
  • ‘Tangled Up in Blue’
  • ‘The Groom’s Still Waiting at the Altar’
  • ‘The Lonesome Death of Hattie Carroll’
  • ‘The Man in Me’
  • ‘The Times They Are A-Changing’
  • ‘Things Have Changed’
  • ‘Thunder on the Mountain’
  • ‘To Ramona’
  • ‘Tombstone Blues’
  • ‘Visions of Johanna’
  • ‘You Ain’t Goin’ Nowhere’
  • ‘You’re a Big Girl Now’