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Back in the 1960s, before the phrase “diss track” became popular, musicians were already taking subtle-and sometimes not-so-subtle-swipes at each other through their songs. One notable example involves Paul Simon and Bob Dylan, two legendary singer-songwriters whose relationship had its rocky moments.
The story dates to 1964, when Paul Simon and Art Garfunkel performed at Gerde’s Folk City in New York’s Greenwich Village. Among the audience was Bob Dylan, along with music critic Robert Shelton from The New York Times. According to Shelton, during the performance, Simon and Garfunkel shared a laugh over something unrelated to the music-a moment that reportedly infuriated Simon.
Years later, Simon disputed Shelton’s version, clarifying, “I wasn’t furious. But I was hurt. Here was someone laughing during my performance-especially someone I admired.”
The following year, Simon released a track widely seen as a sharp parody aimed at Dylan, titled “A Simple Desultory Philippic (Or How I Was Robert McNamara’d Into Submission).” The song originally appeared on Simon’s 1965 UK-only solo album, The Paul Simon Songbook, and later featured on Simon & Garfunkel’s 1966 album Parsley, Sage, Rosemary and Thyme. The lyrics took a clear jab at Dylan, with lines like:
“I knew a man, his brain was so small / He couldn’t think of nothing at all / Not the same as you and me / He doesn’t dig poetry / He’s so unhip, when you say Dylan / He thinks you’re talkin’ about Dylan Thomas…”
Despite the cutting tone, Simon later downplayed the song’s seriousness, describing it as playful. “I was having fun,” he said, noting his enjoyment in crafting a quirky title and incorporating a nod to his favorite comedian, Lenny Bruce. The phrase “How I Was Robert McNamara’d Into Submission” was a direct tribute to Bruce’s style.
Simon’s feelings about Dylan were complex. In a 1972 Rolling Stone interview, he praised Dylan’s early work, highlighting songs like “Blowin’ in the Wind” as melodic and rich, and acknowledging Dylan’s influential role in shaping the folk genre.
However, Simon was less enthusiastic about Dylan’s later material, expressing a clear preference for the Simon & Garfunkel original of “The Boxer” over Dylan’s cover. Still, he admitted to feeling flattered that Dylan chose to perform one of his songs.
Interestingly, despite their ups and downs, Simon and Dylan toured together in 1999, suggesting they eventually reconciled. Yet Simon revealed in 2011 that he never enjoyed being compared to Dylan, candidly admitting, “I usually come in second. I don’t like coming in second.”
He credited Dylan as a major influence in Simon’s early career, saying, “‘The Sound of Silence’ wouldn’t have been written if it weren’t for Dylan.” But Simon also noted that as his own music evolved beyond folk-especially around the time of The Graduate and “Mrs. Robinson”-he felt they had moved in different directions.
The tale of Simon and Dylan offers a fascinating glimpse into the competitive, sometimes contentious, but ultimately respectful relationships among music legends during a transformative era in American music.