Credit: Far Out / Bob Dylan

The 1945 track Bob Dylan could never get enough of: “That song set me off”

Wed 6 May 2026 20:30, UK

It’s nearly impossible for someone to get a handle on where Bob Dylan is going.

He might not have been the most unpredictable artist in the world in terms of genre, but if you show me a person who claims to know Dylan better than anyone else, I would probably be able to show you a bold-faced liar as well. Dylan didn’t let anyone in to see the true Mr Zimmerman underneath it all, and just when you thought that he had a handle on what he was doing, he was moving on to whatever new sound intrigued him.

That’s half the reason why people hated him the minute that he went electric. He was supposed to be the voice of the people who were speaking about real problems affecting the world, and the idea of that same guy having a Fender Stratocaster in his hands, making the same jangly sounds everyone else was doing, was borderline heresy. But given where the rock and roll world was, Dylan was only proving that he could make the best jangly songs that his copycats were trying to make.

He didn’t claim to be married to a specific style, and looking at how his career unfolded, he was more than happy to switch things up on every other record. No one would have thought that the same guy preaching about the indecency of the world would one day be literally preaching from a pulpit on Slow Train Coming, but even in his born-again era, Dylan only needed a few years before moving on to something else.

And while his period in the late 1990s began one of the most intriguing runs of albums in his catalogue, most people didn’t know what to make of him going for easy listening on Triplicate. Here was someone known for going against the grain, so making songs that even the most sheltered grandmothers of the world could appreciate was going to be a bit of a leap compared to everything else.

But that’s only because Dylan genuinely loved this kind of music. He fell in love with how these songs were arranged, and he felt that everything he needed could be found in a tune like ‘Ruby My Dear’ by Thelonious Monk, saying, “Has any of it inspired me as a songwriter? Yeah, ‘Ruby, My Dear’ by Monk. That song set me off in some direction to do something along those lines. I remember listening to that over and over.”

But like any other Dylan switch-up, he was bound to get a few clapbacks from people wondering what the hell he was doing. Roger Waters had no problem calling it one of the worst things that he had ever heard from Dylan, but anyone who was going into the record looking for something new and exciting was probably listening with the wrong mentality whenever they turned on this massive collection.

This was an example of Dylan trying out something new, and while the rest of the world wasn’t as enthused with what they heard, it wasn’t about them liking everything. Dylan wanted the chance to make music that served as a love letter to that era of music, and if Self Portrait taught his fans anything, it was about being patient with him as he went through some of the more questionable pieces of his catalogue.

Because while there’s no reason to think that Triplicate is going to go down in history the same way that Blonde on Blonde is, Dylan needed to get the right songs out of his system so that he could pave the way for something greater. Sure, some of his records are going to be more than an acquired taste, but none of the critics should matter when he has the right amount of passion behind what he’s singing.