A “Drained” Bob Dylan Nearly Quit Music Altogether in 1965: Behind the Writing Session That Changed Everything

Bob Dylan’s legendary career took off fairly quickly. However, the hit singer/songwriter behind tunes like “Lay Lady Lay” and “Knockin’ On Heaven’s Door” had a few years to contemplate whether or not he was actually going to make it in the music industry; and if he even wanted to. Surprisingly, Bob Dylan almost didn’t make it and was ready to quit in the 1960s. But one particular writing session changed everything.

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The Freewheelin’ Bob Dylan was released in 1963, shortly after the artist turned 22 years old. It was a legendary piece of work that pulled Dylan from the small folk venues in Greenwich Village into international stardom. He was considered a pioneer of political folk-rock music after that record was released. He toured Europe, and all looked well for the rising star. Unfortunately, Dylan didn’t feel great about it.

Why Did Bob Dylan Almost Quit Music?

Dylan struggled from 1963 to 1965. He blew off The Ed Sullivan Show, was criticized for comments he would make during live sets, and felt that he no longer was welcomed in the folk-rock and political music scenes that formed his identity as a musician. According to Dylan himself, he was ready to quit singing altogether.

“I was going to quit singing,” Dylan said of that period in his career. “And I was very drained, and the way things were going, it was a very draggy situation. I was playing a lot of songs I didn’t want to play. I was singing words I didn’t really want to sing. It’s very tiring having other people tell you how much they dig you if you yourself don’t dig you.”

After wrapping up a tour in England in 1965, that urge to quit music entirely hit hard. He even told his manager he was ready to quit. Bringing It All Back Home was just released and met with lukewarm reviews, and his fans were mad about the introduction of the electric guitar to his sets. Luckily, though, everything changed that very year.

While slinking away from the public eye into Woodstock, New York, Dylan got to writing. According to Dylan, the initial “script” for Highway 61 Revisited was 10 (or 20, depending on which interview you read) pages long. That massive tome of written songs included the foundation of “Like A Rolling Stone”, Dylan’s biggest career hit to date.

“I’d never written anything like that before and it suddenly came to me that was what I should do,” Dylan said of the song and the art of songwriting in general.

Dylan finished the song up, recorded it, and released it in 1965. It hit no. 2 on the Billboard Hot 100 and stayed on the charts for 12 weeks. And, of course, the rest is history.

Photo by Michael Ochs Archives

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