“She’s talented”: the pop star Bob Dylan couldn’t help but praise

The relationship between Bob Dylan and the mainstream has always been at arm’s length to a certain degree.

There are more than a few times where he has crossed over and made the kind of tunes that could work on the radio, but even after bowing out of the pop world sometime after the 1970s, it’s not like the rest of the audience forgot about him. Everyone was endlessly fascinated as to where he would go on every single record, but Dylan felt much more comfortable working outside the pop framework.

Then again, Dylan’s approach was never about getting chart success. It probably didn’t hurt to have some of the most highly-regarded songs of the 1960s in his back pocket every single time he performed, but the model that he was using wasn’t about the biggest hits. He wanted to carry on the tradition that Woody Guthrie had been doing with his music, and that meant thinking outside the box and making the kinds of tunes that suited how he was feeling at any given moment.

And when you look at where pop music was headed around the early 1980s, Dylan probably found the best time to get off that merry-go-round. It’s impossible to think of him doing any of the strange choreographed dance moves that everyone else was doing on MTV, and even if he was making a dramatic turn into Christian music, the idea of him making a video for ‘Man Gave Names to All His Animals’ would have been unintentionally hilarious.

But most of the biggest names in music at the time weren’t always about Dylan’s model for songwriting. Michael Jackson wasn’t going to be making the same kind of social commentary Dylan was making just yet, and Prince was slowly turning rock and roll inside out by making more funky material, but Madonna seemed to have some of the most inspired visuals that anyone had ever seen.

By which I mean that they pissed everyone off whenever she sang. No one was quite ready for a pop singer being this overtly sexual since the days of Elvis Presley, and by those standards, ‘The Material Girl’ made ‘The King’ look like a choirboy. She was looking to test the boundaries of anything and everything that she was doing whenever she worked, and while that would have been a big turn-off for Dylan, he felt that she was the one person who seemed to understand her role as a performer.

Dylan wasn’t going to suddenly start making covers of ‘Vogue’ or ‘Papa Don’t Preach’, but he felt that Madonna was one of the few pop stars out there that had him interested in where she was going, saying, “Pop entertainment means nothing to me. Nothing. You know, Madonna’s good. Madonna’s good, she’s talented, she puts all kinds of stuff together, she’s learned her thing … But it’s the kind of thing which takes years and years out of your life to be able to do.”

And that kind of momentum that Madonna had from working all those years is what makes her just as relevant today as she was back then. She wasn’t going to have the same kind of draw that modern pop stars do, but when you listen to some of those tracks from back in the day or even the more modern stuff like ‘Hung Up’, she’s constantly pushing herself into new areas not unlike what Dylan has been doing ever since the 1990s.

She probably doesn’t have a song like ‘Murder Most Foul’ under her belt or anything, but that’s not what she signed up for when making her classics. She wanted the chance to get people dancing, and even if she was a bit more risque than the average pop star, she was going to do everything she could to make sure the audience never forgot a second of what he did at every show. 

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