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‘The Freewheelin’ Bob Dylan’: Inside His First Classic

Dylan broke with folk orthodoxy, recorded his own songs and made a masterpiece

“I wrote a lot of songs in a quick amount of time,” said Bob Dylan of the creative explosion that resulted in his second album, 1963’s The Freewheelin’ Bob Dylan. “I could do that then, because the process was new to me. I felt like I’d discovered something no one else had ever discovered, and I was in a sort of an arena artistically that no one else had ever been in before ever.”


Dylan’s second LP was not only his first genuine masterpiece, it was also a landmark in the very way that popular music was created. After writing just two songs on his 1962 debut, he wrote 12 of the 13 songs on Freewheelin’ – including such classics as “Blowin’ in the Wind,” “A Hard Rain’s A-Gonna Fall” and “Don’t Think Twice, It’s All Right” – permanently altering the relationship between singer and songwriter. And he did so with a collection of compositions that displayed a dizzying range, from blistering social commentary (tackling such topics as civil rights and nuclear holocaust) to nuanced romance, from comic talking blues to melancholy heartbreak.

When the Beatles were first given the album by a French DJ, they could listen to little else. “For three weeks in Paris, we didn’t stop playing it,” said John Lennon. “We all went potty about Dylan.”

Unlike his debut LP (and unlike most of his albums to follow), Freewheelin’ was a project that Dylan, just 20 years old when recording began, took his time with. Where Bob Dylan was cut in just two days, this album was crafted over no fewer than eight separate visits to the studio, spanning a full year from April 1962 to April 1963. Over the course of those months, he continued to revise and refine the song selection, trying desperately to keep up with the breathtaking, high-speed evolution of his writing.

Though the world didn’t know it yet, Dylan had been writing songs nonstop since arriving in New York in 1961. “He was writing all the time, at night sitting in the clubs,” says Peter Yarrow. “You’d see him reading a newspaper, and then the next day he wrote a song about what he had read.”

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The album was also informed by the constant influx of new experiences and ideas affecting Dylan at the time – a burgeoning political awareness, his first trip overseas, the entrance of Albert Grossman as his manager. Above all, though, Freewheelin’ revealed the impact of his girlfriend Suze Rotolo, depicted huddling with Dylan on a snow-covered Jones Street for the album’s iconic cover. (“The cover’s the most important part of the album,” he would say to his friends.) 

Rotolo was studying art in Italy during most of the album’s creation, and Dylan’s longing, even his anger, during her absence impacted many of these songs. Also crucial was the effect of Rotolo’s activist family on Dylan’s worldview; both of her parents were members of the American Communist Party. Suze “was into this equality-freedom thing long before I was,” he said.

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