Bob Dylan couldn’t even play free shows when he moved to New York: ‘He was too raw’

Bob Dylan moved to New York with the intention of establishing himself as a musician. He did so, but not without some challenges. When he arrived he didn’t make a strong impression; No one was very impressed with his singing or guitar playing, and he struggled to find places that would hire him for shows. They saw it as an act that could clear a space, not bring in an audience.

A black and white image of Bob Dylan wearing a hat and playing guitar in front of three microphones in a club in New York.
Bob Dylan | Sigmund Goode/Michael Ochs Archive/Getty Images

Bob Dylan struggled to find work when he moved to New York

Dylan moved to New York from Minnesota to follow in the footsteps of his hero, Woody Guthrie. When he arrived, he quickly set himself apart from his fellow musicians. According to musician Dave Van Ronk, Dylan looked like “the worst-looking escapee from a cornfield I’ve ever seen” (via The Ballad of Bob Dylan: A Portrait by Daniel Mark Epstein). His take on the harmonica was messy and untrained. Still, Van Ronk said he found Dylan impressive.


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