(Credits: Far Out / GAC / General Artists Corporation / Columbia Records / Alamy)
Tue 27 January 2026 0:00, UK
A lot of people fantasise about their favourite artists of an era coming together and collaborating, but if your two icons in the 1960s were Frank Zappa and Paul Simon, then you’d be forgiven for thinking that it was perhaps off limits.
Obviously, there’s not much linking the two artists stylistically, with Zappa being a jazz-rock oddball known for his satirical jabs at the rest of the music world, and Simon being best known for writing some of the most earnest folk songs of the era alongside his then-partner, Art Garfunkel. To think that this would work in any way is a long stretch, and not something that many people would have been demanding.
At the same time, there was nothing stopping the two from being fans of each other, but you also wouldn’t bet on it either. Zappa was known as something of a crotchety snob who was very particular about the music that he listened to, and who was very outspoken when he didn’t believe something was of any merit, while Simon outwardly appeared much more reserved and gentle with his comments about the work of his contemporaries.
However, despite the unlikelihood of the two ever crossing paths, let alone working alongside each other, fortune can sometimes strike in the most wonderful and unpredictable fashion, and in 1969, Zappa would find himself teaming up with Simon and Garfunkel in rather fortuitous circumstances.
While Zappa claimed from his own accounts that the meeting happened a couple of years earlier, it was at the tail end of the decade when he and Simon met in Manny’s Music Store, an instrument shop in New York, and Simon ended up inviting his new acquaintance over to his house for dinner later that evening, where things took an unexpected turn.
According to Zappa, the entire evening was peculiar from the get-go, which, given Zappa’s predilection for out-there behaviour, says a lot about how perplexed he was by the situation. “As I walked in the door, Paul was on his hands and knees in front of what appeared to be a Magnavox stereo,” he recalled. “He had his ear right up to the speaker, listening to a Django Reinhardt record.”
Garfunkel would then arrive later, and the three would end up discussing Simon and Garfunkel’s early years performing as Tom and Jerry, and it was at this point that things took an even more peculiar spin, with Zappa making a proposition.
“I said, ‘Well, I can understand your desire to experience the joys of touring once again, and so I’ll make you this offer,’” he began. “‘We’re playing in Buffalo tomorrow night. Why don’t you guys come up there and open for us as Tom and Jerry? I won’t tell anybody. Just get your stuff and go out there and just play only your old stuff, no Simon and Garfunkel tunes.’ They loved the idea and said they would do it.”
While the audience at the show was stunned by the fact that they’d not only been treated to a performance from Zappa, but Simon and Garfunkel in disguise as their former selves, it was surely a sequence of events that nobody could have predicted, and a rather special moment in the history of rock where two seemingly opposing forces converged for a memorable spectacle.
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