
The guitarist Paul Simon knew was out of his league: “I can’t”
Not every artist is looking to be the world’s gift to instrumentalists. The best musicians of their generation are usually the ones who know their capabilities and end up going above and beyond their limitations to make something that no one else thought was possible.
Although Paul Simon was already one of the best acoustic players in the folk rock scene, and distinctly underrated outside of that niche, he knew that nothing could make him sound as good as one particular great. But maybe even that modesty is why he’s such a good guitarist, imbuing his playing with sincerity and nuance rather than showing off.
Simon is perfect when it comes to harmonising the major scale and that gives his songs a distinct sound and feel. As the Grammy-winner Steve Earle said in praise of Simon, “He’s like a craftsman on another level.”
His ability to perfectly pair his words with just the right note is a phenomenal skill. “He obviously works and works and works at it, because he learned it in the Brill Building,” Earle told Rock Cellar. “But he also genuinely had one foot in Greenwich Village too, because of the age he was, and he understood it and he listened to all those records and he learned to play guitar like that.”
Considering what he did with Simon and Garfunkel, though, Simon deserves far more attention than he receives for his picking technique. Despite his reputation as a delicate player who is known to keep a steady pulse throughout a tune, that metronomic playing is what defines tunes like ‘The Sound of Silence’, almost providing a subtle heartbeat for him and Art Garfunkel to lay their heavenly harmonies over the top of.

Even when working with African musicians during Graceland, he was always willing to bend his usual technique to suit whatever the song needed. The title track, for instance, was based on that travelling beat that most people know from montages in movies, but hearing the musicians interpret it in their own way led to the song taking on a much more fluid beat than something Simon could have come up with on his own.
That’s before getting into his chord work, as well. Looking through a tune like ‘50 Ways to Leave Your Lover’, Simon was never content to play the same thing twice, which normally meant twisting chords around and throwing in upper extensions to make the whole thing sound closer to a jazz take on a pop song rather than the customary pop fare on the radio.
As much as Simon knew about the intricacies of guitar, he felt that Django Reinhart was still the gold standard for what someone like him could live up to. Even though he only had use of two of his fingers on the guitar, the beauty that Reinhart got out of the instrument can’t be overstated, usually taking a few chords and turning them into the kind of jazz that took most people years to figure out despite having full use of all of their fingers.
While Simon was still fresh out of Simon and Garfunkel when making his debut solo record, he knew that he couldn’t match what Reinhart did when working next to jazz violinist Stephane Grappelly, saying, “Hobo’s Blues’ we did with Stephane Grappelly, the French jazz violinist.” Humbly admitting that he knew the legendary strummer was required to craft that Reinhart-like sound that was out of his league.
As Simon continued, “Originally, I just wanted Grappelly to play. I can’t do what Django Reinhardt did on guitar when he played with Grappelly. So we made up a chord structure, and we just wound up doing this jam.”
But the beauty behind jazz is that jamming spirit, and when listening to the recorded version of ‘Hobo’s Blues’, it’s easy to hear both of them listening to where the other is going. After all, jazz is meant to be like a conversation between players, and hearing Simon interpret Reinhart’s style in his own way is a breath of fresh air compared to where he had been on Bridge Over Troubled Water.
Yet, it is perhaps the finest measure of Reinhart’s ability that even guitarists from disparate genres were inspired by him. The heavy metal hero Tony Iommi called him an inspiration, Jeff Beck said Reinhart was “superhuman”, and Jerry Garcia said he hadn’t heard such personality-filled playing “anywhere else.” So, no wonder Simon thought he couldn’t compete and turned to, Grappelly, his closest companion.
Then again, this wasn’t a case of trying to match what Reinhart had done in his prime. It was a matter of broadening his musical palette, and with only a handful of chords and Grappelly there with him, Simon managed to internalise that jazz vocabulary with ease