Credit: Far Out / Album Cover
Wed 29 July 2026 20:30, UK
Paul Simon has always shot straight whenever he wrote any of his songs.
Not every tune of his had to be about his actual life by any means, but when you look at the kinds of topics that he was talking about, you could definitely tell how he was feeling when he wrote a song like ‘50 Ways To Leave Your Lover’ compared to the jubilation all across records like Graceland. But even if Simon took a lot of inspiration from the rougher parts of his life, he wasn’t shy about talking about the moments where nothing could possibly go wrong, either.
In fact, that’s half the reason why Simon had a problem with his own singing a lot of the time. He was nothing if not sincere throughout every single one of his songs, and since so many of his greatest tunes revolved around him having his usual laid-back demeanour to every single one of his songs, it was hard for him to take on any kind of character that sounded sarcastic in any of his songs the same way that someone like Bob Dylan could.
But sincerity isn’t a bad thing, either. If anything, it’s a lost art in the world of songwriting, and there aren’t many people who were doing what Simon could do back in the day. There was hardly any other artist who would have been willing to make the trip to South Africa and work with world musicians to flesh out their songs, but Simon would do anything if it meant that he could learn something new about how someone approached their craft.
Because when you look at some of the biggest hits that he had during the first half of his career, they were something a bit more naive about what he was singing about. Simon and Garfunkel didn’t shy away from singing about serious topics every single time they worked on one of their records, but compared to the wild political songs from around that time, they were definitely on the softer side of what rock and roll was supposed to sound like.
Simon never claimed to be on the same level as someone like Led Zeppelin, but when you listen to how he and Art Garfunkel sang together, there was never any sense that they were trying to make anything too cerebral for their fans. Their music was a lot more approachable than most other folk artists, and while Simon did cringe a little bit at some of his songs from back then, he couldn’t help but smile when thinking back on those times.
Yes, the songs themselves were more than a little bit dumb back in those days, but compared to his solo career, Simon credited Simon and Garfunkel for giving him some of the greatest years he ever had in the music industry, saying, “There’s something naive and sweet-natured and I must say I like that about it. They’re not angry. And that means that I wasn’t angry or unhappy. And that’s my memory of that time: it was just about idyllic. It was just the best time of my life, I think.”
Further reading: From The Vault
That doesn’t mean that Simon necessarily likes everything that he made around that time. He has said numerous times that he would rather play anything else than ‘The 59th Street Bridge Song’, but even that tune has a bunch of moments that feel a lot more carefree than some of the more serious subject matter that he would get into when working on records like Hearts and Bones later down the line.
The reality of being a rock and roll star hadn’t quite kicked in yet, and while Simon would have a lot more great songs to come after he left the duo, he was never going to forget those good times that they had together. He may not want to play some of those songs again, but there’s also a good chance that no one else could have been able to write with that much of a carefree attitude later in their career.
