The five best songwriters ever, according to Bob Dylan

Anyone who’s ever considered taking up songwriting is going to end up going through their Bob Dylan phase without realising it.

Despite the questionable stuff he’s released in his later years, Dylan has always been one of the truly great poets of rock and roll and has done everything he could to make sure that he kept up his track record of writing the greatest prose anyone has ever heard. And yet, when looking at some of his idols, it’s no surprise where he gets a lot of his genius from.

Because, beyond being a brilliant musician, what makes Dylan so magical is the way that he’s able to tell a story through his tunes. Most other artists would have normally found a niche and stuck with it, but from the political rhetoric of The Freewheelin’ Bob Dylan to the heartache of Blood on the Tracks, Dylan wasn’t only trying to make the best music he could. He was testing what could be done with the song format when someone decided to take more of a chance. 

A lot of that comes from the folk tradition, but it’s not like he was going to ignore what was happening in the rock and roll scene, either. The best songwriters of his generation started off in the same place he did, and while he might not have known as many chords as his peers, he knew that he was going to save some of that wisdom for when it came time for him to write another one of his classics.

Were all of them going to work? No, but that’s just the nature of the beast. For as much material as Dylan has put out, the classics will speak for themselves years after he’s gone in the same way that people will be singing his idols’ songs when looking back on the legacy of all 20th-century music.

The five best songwriters of all time, according to Bob Dylan:

John Prine

John Prine - 1979 - Musician

In the aftermath of Dylan, there was no shortage of people trying their best to sound exactly like him. Imitation might be the sincerest form of flattery, but when looking at Dylan’s trajectory, chances are he would have much rather had his own sound than worrying about people like Barry McGuire doing their own takes on what he was already talking about. But when you listen to John Prine, you’re getting the kind of folk music that is unlike anything else on this Earth.

While Prine was never on Dylan’s level in terms of popularity, Dylan knew that he wrote songs in a way that nobody else could copy, saying, “Prine’s stuff is pure Proustian existentialism. Midwestern mindtrips to the nth degree. And he writes beautiful songs. I remember when Kris Kristofferson first brought him to the scene. All that stuff about ‘Sam Stone’, the soldier junky daddy, and ‘Donald and Lydia’, where people make love from ten miles away. Nobody but Prine could write like that. If I had to pick one song of his, it might be ‘Lake Marie’.”

But it’s more than just the flowery language that got Dylan’s foot in the door when it came to Prine’s songwriting. Everyone might have been an amalgamation of all their influences, but when looking at the millions of Dylan knockoffs that blossomed into truly great artists, there still isn’t a soul on this Earth who can manage to sing or write at Prine’s level.

Gordon Lightfoot

Gordon Lightfoot - Far Out Magazine

Dylan always took a bit of pride in liking music that was a little bit left-of-centre when it came to the pop charts. Gene Simmons might be one of the first people to say that Mr Zimmerman was among the finest artists to ever pick up a pen, but was anyone really looking at any of Kiss’s lyrics and thinking that they were anywhere on that level? For Dylan, he needed a songwriter who had a little more meat in every song he sang, and Gordon Lightfoot practically made it his mission to make incredibly detailed character portraits.

Although most people would know him for ‘The Wreck of the Edmund Fitzgerald’, Dylan knew that Lightfoot’s catalogue was a virtual goldmine waiting to be stumbled upon for anyone even mildly interested, saying, “I can’t think of any Gordon Lightfoot song I don’t like. Every time I hear a song of his, it’s like I wish it would last forever… Lightfoot became a mentor for a long time. I think he probably still is to this day.”

And Dylan isn’t even the only one holding him in such high esteem. While Lightfoot might not have had the same kind of megahits as his contemporaries, hearing songs like ‘If You Could Read My Mind’ being covered by some of the most well-respected singers of all time, like Johnny Cash, was more than simple lip service. It was doing justice to one of the finest writers of his generation and reminding everyone of the kind of beauty someone could create with only a few lines of prose.

Randy Newman

Randy Newman - Musician - 1975

Not every Bob Dylan necessarily needed to wow all of the musos in the audience. Half of his early career could have been summed up by him playing a bunch of basic cowboy chords, so it wasn’t like everyone was looking for him to make the kind of Steely Dan-style chord progressions in his songs. That’s not to say that he couldn’t still appreciate it when people like Randy Newman came along, though.

While Newman could throw in a million different chords and weave together the most beautiful song ever written, Dylan felt that his lyricism was severely overlooked half the time, saying, “There’s a lot of people who write good songs. As songs. Now Randy might not go out on stage and knock you out, or knock your socks off. And he’s not going to get people thrilled in the front row. He ain’t gonna do that. But he’s gonna write a better song than most people who can do it.” And that shows in every single era that he was writing in.

It was easy to see him fitting right in alongside people like James Taylor when writing tunes like ‘Sail Away’ and ‘Short People’, but the kind of social commentary in his tunes is what kept Dylan coming back for more every time he saw him. He wasn’t trying to be the greatest singer in the world by any stretch, but even when he started working for Disney, Newman gave children’s entertainment some of the most in-depth songs of his career.

Paul McCartney

Paul McCartney - 2021 - Musician - The Beatles -

There wasn’t a single member of The Beatles who couldn’t say that Bob Dylan fundamentally enriched their life. The Fab Four had been fans since the days of The Freewheelin’ Bob Dylan, but there was also a bit of a competition going on whenever Dylan and John Lennon started trading similar songs back and forth in their prime. But even after being in a band with George Harrison, Dylan had to admit that there was something about McCartney that never ceased to amaze him.

Whereas the entire band worked so well together, Macca blew Dylan away every single time he heard one of his melodies, saying, “I’m in awe of Paul McCartney. He’s about the only one that I am in awe of. But I’m in awe of him. He can play any instrument. He can scream and shout as good as anybody, and he can sing the ballad as good as anybody, you know, so… And his melodies are, you know, effortless.”

Even when McCartney wasn’t even working on his tunes, he was thinking about that melodic structure as well, whether that was paying attention to what people like Brian Wilson were doing or turning Harrison’s ‘Something’ into one of the greatest bass lines in pop music history. Although Dylan catered to the kind of songwriters who could tell a story within the span of a few minutes, McCartney has reached the point of being one of the best all-around musicians that rock has to offer.

Woody Guthrie

Woody Guthrie - Musician

Everything that made Bob Dylan one of the greatest songwriters of his time always came back to the world of folk music. Although his electric period showed everyone what could happen when you combine genres, the heart of all his music was to carry on the kind of communal spirit that he heard from some of the greatest musicians from the pre-rock and roll era. And while Pete Seeger managed to be an excellent guide half the time, Woody Guthrie was the one who spoke the kind of truth that Dylan wished he could.

But Dylan’s obsession with Guthrie was about more than the music. On tunes like ‘This Land is Your Land’, the folk icon had the kind of emotional honesty that Dylan would claim as his own only a few years later. Compared to every other musician that he idolised, something about Guthrie felt like a religious experience to Dylan, saying, “I said to myself I was going to be Guthrie’s greatest disciple. [He was] the true voice of the American spirit.”

Even when he was unable to perform, Dylan went to see Guthrie when he was ill to pay his respects to the person who gave him the drive to write the feelings that everyone else might have been a bit too afraid to express back in the day. Dylan may have been one of a kind by rock and roll standards, but the fearlessness in his music had always come from that voice of a generation that fell all too silent years before most had stopped listening.

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