Bob Dylan moved to New York with the intention of establishing himself as a musician. He succeeded, but not without some difficulties. He did not make a strong impression upon his arrival; no one was very impressed with his singing or guitar playing, and he struggled to find places that would hire him to play shows. They saw it as an act that could clean up a room, not draw in the audience.

Bob Dylan struggled to find work when he moved to New York
Dylan moved from Minnesota to New York to follow in the footsteps of his hero, Woody Guthrie. Upon his arrival, he was quickly noticed by his fellow musicians. According to musician Dave Van Ronk, Dylan looked like “the scruffiest fugitive from a cornfield I think I’ve ever seen” (via The Ballad of Bob Dylan: A Portrait by Daniel Mark Epstein). His approach to the harmonica was haphazard and untrained. Still, Van Ronk said he found Dylan impressive.
“His singing had the same prisoner-free delivery as his harmonica playing,” he said. “We were impressed.”
However, not everyone felt the same. He dressed poorly and did not sing or play guitar as well as his peers. He brought a nervous energy to the scene. Because of this, he struggled to find work.
“He was too raw,” Van Ronk said.
According to Epstein, many club owners wouldn’t even let Dylan play for free.
“He was the kind of act you would do near closing time to empty a room,” Epstein wrote.
Has this vision of Bob Dylan’s music ever changed?
Van Ronk’s recollection of Dylan’s early days in New York proves one thing: he was always a divisive artist. He may no longer have trouble finding places to perform, but people have long questioned Dylan’s appeal. His writing is rarely questioned, but his singing voice is.
Dylan has grown as an artist since his early days in New York — he was mostly trying to look like Guthrie in the early 1960s — but the way people see him hasn’t changed all that much. On the contrary, it shows Dylan’s strength as an artist. Despite certain opinions about him, he managed to establish himself as one of the most influential musicians of all time with his songwriting.
Bob Dylan helped establish New York’s folk music scene
Dylan moved to New York in the early 1960s in order to succeed as a musician. According to Van Ronk, he was lucky to have done this. While there were a number of folk musicians in the city, few, if any, could make a living from their music alone.
“I heard it said. . . that he came to New York to ‘do’ but that’s *** bullshit,” Van Ronk said. “When he came to New York, there was no big folk music scene.”
Dylan grew up as a musician thanks to the artists he met while living in New York. He also helped make the city, and Greenwich Village in particular, a hub of folk music.