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The one song that defines Bob Dylan at his very best

Tue 14 April 2026 18:00, UK

There’s no real accurate way of describing what Bob Dylan is like to anyone.

Even though there are many people that have been following his music for centuries, there are hardly any moments where even his most hardcore fans can say that they know who the real Mr Zimmerman is underneath all of those musical masks. He does leave a lot of his most emotional moments for when he’s actually singing, but Dylan was more interested in searching for other musical masks out there in the wild.

Because while anyone can get to the top of the charts by trying to match what the biggest names in music were doing, the ones who stick around gave the people what they didn’t know they wanted. There was no real explanation for why a band like The Beatles managed to take over people’s hearts so quickly when they started, and even decades after the fact, there was even less of an explanation for the next biggest name in music to be Kurt Cobain at the height of hair metal.

And while the biggest names in pop follow the same principles, there’s a big reason why Dylan couldn’t recognise himself years after the fact. He liked the idea of constantly evolving every single time he made a new record, but when you look through his collection of classics, he’s not exactly playing the hits the same that he used to whenever he started working on some of his masterpieces.

If you think about it, the fact that Dylan was able to shift things around that much in such a short amount of time makes him even more of a chameleon than David Bowie. Bowie was the one looking to transform his singing style and genre every time he sang, but Dylan was far more interested in having a different approach to the lyrics and the characters that he played in every one of his songs.

So when he sees the version of him that he used to be, Dylan felt that he didn’t even recognise that kind of person anymore, saying, “I see Nat King Cole, Nature Boy – a very strange enchanted boy, a terribly sophisticated performer, got a cross section of music in him, already postmodern. That’s a different person than who I am now.” He may have been strange, but it was exactly what that generation needed to get up off their ass and start asking questions.

The Dylan of old was interested in making musical parables every single time he stepped up to the microphone, and even if he had more of a messianic complex than he really wanted, he could lean into it on occasion. He wanted to fight for what was right, and even when the media tried to get a straight answer out of him, he knew that they were never going to truly get one when they started talking about the meaning behind his songs.

He could still deliver to the audience, but the comparison between him and Nat King Cole is a lot more strange than people realise. Cole’s greatest strength was being able to bring that air of sophistication to everything, but since Dylan was known for dismantling everyone’s notions of what a rock and roll show should be, the version that we see today is even less interested in following conventions, usually trying his best to keep the audience on their toes every time they hear one of his concerts.

It might sound like a more aggressive way of going about it, but Dylan wasn’t about to try and make songs that were safe for the rest of us. He did eventually embrace his inner crooner like Cole when making Triplicate, but when going through his history, the only thing that Dylan could ever hope to do was keep his audience guessing, even if it meant killing off the persona that people loved.