A black and white picture of Bob Dylan wearing a hat and playing guitar in front of three microphones at a club in New York.

Bob Dylan moved to New York with the intention of establishing himself as a musician. He succeeded in this, but not without some challenges. He didn’t make a strong impression when he first arrived; nobody was very impressed with his singing or guitar playing, and he struggled to find places that would hire him to play shows. They saw him as an act that could clear a room, not bring in audiences.

A black and white picture of Bob Dylan wearing a hat and playing guitar in front of three microphones at 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 from Minnesota to New York to follow in the footsteps of his hero, Woody Guthrie. When he arrived, he quickly stood out to his fellow musicians. According to musician Dave Van Ronk, Dylan looked like “the scruffiest-looking fugitive from a cornfield I do believe I had 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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