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“Pop entertainment means nothing to me”: The only pop star Bob Dylan ever liked

Sun 3 May 2026 4:00, UK

Bob Dylan’s musical opinions vary. Some of his favourite artists are obvious and expected, like his love for Hank Williams or the great blues players, while some seem to make no sense at all, like his later obsession with Machine Gun Kelly.

Either way, Dylan clearly has a lot of opinions when it comes to songs, so much so, in fact, that instead of delivering the long-promised follow-up to Chronicles or any kind of traditional memoir, he turned into a music journalist and released The Philosophy of Modern Song.

In the book, he meanders through music, touching on some of his favourite songs and artists, musing on what makes music good or a band or sharing memories of particular songs. He does our job pretty well, and if he weren’t in his 80s, he’d be putting journalists everywhere at risk. But even despite sharing so much about his musical opinions, they still feel mythical and baffling. They also feel flimsy, as in one interview, he’ll tear down The Beatles, in another, he’ll big them up. There’s the sense that you can never quite take what he says as anything set in stone.

Take, for example, Dylan’s opinion on pop music, shared with veteran writer Paul Zollo. “Pop entertainment means nothing to me. Nothing,” he spat. That would seem definitive, right? Emphasising the “nothing”, that quote could be clipped right there, and the line could be that Bob Dylan, folk legend, rock pioneer, musical god, hates pop. But then the artist instantly complicates things, offering up an exception.

“You know, Madonna’s good. Madonna’s good, she’s talented, she puts all kind of stuff together, she’s learned her thing,” he says. Suddenly, it’s clear that obviously not all pop is bad in his books. His opinion had a crack in it, and that crack comes in the form of Madonna’s first records, with Like A Prayer being released as the last album before this 1991 interview.

And so the opinion changes to Dylan doesn’t hate pop, it’s just that he could never make it. “It’s the kind of thing which takes years and years out of your life to be able to do. You’ve got to sacrifice a whole lot to do that,” he said, seemingly actually having really major respect for artists like Madonna who put in the effort to make something special.

Perhaps the actually sonics don’t really do much for his more folk and rock adjacent ear, but in reality, rather than writing all pop off as trash, it’s clear that the reality of Dylan’s take is that while it might not be for him, he recognises the level of strife that goes into the theatrics and artistry of pop, and the effort it takes to craft a song.

Madonna stands as the pinnacle of that, both to Dylan and arguably to the entire pop world. Here we have a star who has not only reinvented the pop world with her engagement with the queer community, her inspiration from the NYC art world and her connection to people like Basquiat. No one could ever argue that Madonna is stupid or vapid, as clearly, her pop music comes from a place of great intelligence and genuine knowledge.

With her various references, both musical and visual, as well as her knack for crafting timeless earworms, she’s the gold standard of pop stars, and while he might not be listening on repeat, Dylan still has to recognise and respect that game.