Paul Simon Hated Being Compared to Bob Dylan, but He Wished He Could Sound More Like Him in 1 Unique Way

Paul Simon and Bob Dylan both rose to prominence in the 1960s with similar styles of music. Naturally, people drew comparisons between the two musicians, which Simon resented. He was competitive and didn’t think he and Dylan were a match on a philosophical level. Still, he attempted to emulate one unique feature of Dylan’s voice. He said he was never able to achieve it, though.

A black and white picture of Bob Dylan and Paul Simon playing guitar onstage together.
Bob Dylan and Paul Simon | Larry Hulst/Michael Ochs Archives/Getty

Paul Simon didn’t appreciate the way Bob Dylan put people down

Simon always admired Dylan, but he began to take issue with the “Tangled Up in Blue” singer when he drunkenly laughed all through a Simon & Garfunkel show. Though writer Robert Shelton, who was with Dylan, insisted it wasn’t malicious laughter, it hurt Simon’s feelings.

“I wasn’t furious,” he said, per the book Paul Simon: The Life by Robert Hilburn. “But I was hurt. Here was someone laughing during my performance — especially someone I admired.”

Simon believed that Dylan had a problem with putting people down, which set them apart as musicians. 

“Unfortunately, I’m always being compared to Bob Dylan,” he said, per the book Homeward Bound: The Life of Paul Simon by Peter Ames Carlin. “Our philosophies are different. He is always dumping [on] people more than I do. It’s really easy to put somebody down. The biggest thing Dylan has going for him is his mystique.”

Paul Simon wished he could emulate 1 feature of Bob Dylan’s singing 

Simon considered himself highly competitive and wanted to be seen as an artist in his own right. Because of this, he resented comparisons to Dylan.

“I usually come in second to (to Dylan), and I don’t like coming in second,” he told Rolling Stone (via The Guardian). “In the beginning, when we were first signed to Columbia, I really admired Dylan’s work. The Sound of Silence wouldn’t have been written if it weren’t for Dylan. But I left that feeling around The Graduate and ‘Mrs. Robinson.’ They weren’t folky anymore.”

Still, he wished he could emulate the irony and double meaning that featured in Dylan’s songs. 

“One of my deficiencies is my voice sounds sincere. I’ve tried to sound ironic. I don’t. I can’t,” he said. “Dylan, everything he sings has two meanings. He’s telling you the truth and making fun of you at the same time. I sound sincere every time.”

The two musicians toured together

Though Simon had problems with Dylan, the two musicians toured together in 1999. They alternated as headliners and played several songs together. Before embarking on the tour, they met at Simon’s apartment to play music together.


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“We were singing folk songs,” Simon said, per Rolling Stone. “Some were obscure, some were better known. It was just two acoustic guitars and it sounded great. But as we got closer to the show, it became apparent what people wanted to hear was us singing each other’s songs. So that’s what we did.”

Together, they performed songs like “The Sound of Silence,” “Knockin’ on Heaven’s Door,” and “Forever Young.”