In early 1961, Bob Dylan arrived in New York City in search of a career in music. He found a community in the city that offered to teach him and give him a couch to crash on whenever he needed one. When he first arrived in New York, though, many of his future friends had no idea what to make of him. His appearance and dedication to music, despite a lack of experience, puzzled them.
1. Bob Dylan’s appearance stood out to his new friends in New York
Dylan arrived in New York as a 19-year-old seeking out his idol, Woody Guthrie. Like Guthrie, he wanted to make his way in the city. While musician Ramblin’ Jack Elliott described him as “cute,” many others took note of Dylan’s scraggly appearance.
“[Dylan] was the scruffiest-looking fugitive from a cornfield I do believe I had ever seen,” musician Dave Van Ronk said, per the book The Ballad of Bob Dylan: A Portrait by Daniel Mark Epstein.
Later that year, a Cambridge club owner offered a similar assessment.
“I vividly remember Bob Dylan coming in as a really scrawny, shabby kid,” Paula Kelley told WBUR. “He’s the only person I’ve ever seen with green teeth.”
2. His handshake was slightly off-putting
Though Dylan had a scarecrow quality that surprised many of his new acquaintances, they couldn’t help being impressed by his musicianship.
“His singing had the same take-no-prisoners delivery as his harmonica playing,” Van Ronk said. “We were impressed.”
When Van Ronk went to introduce himself to Dylan for the first time, he took note of his “famous dead-fish handshake.”
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Since that early point in his career, a number of other people have met Dylan’s limp handshake with surprise.
3. New York club owners didn’t think Bob Dylan seemed prepared to play shows
Dylan’s biggest problem when he arrived in New York was his experience level. He’d performed with bands in high school and played in coffee shops during his short-lived college career. Beyond that, though, he was relatively green. Club owners immediately noticed his youth and nerves and refused to hire him.
“Nobody wanted to hire Bobby,” Van Ronk said, per the book Down the Highway: The Life of Bob Dylan by Howard Sounes. “He was too raw.”
Many places wouldn’t even let Dylan perform for free, worrying he would drive away crowds. Others didn’t like that Dylan, a 19-year-old from Minnesota, seemed to be adopting a persona that didn’t fit him.
“I wasn’t crazy about Dylan’s music,” club owner Manny Dworman said. “To me he looked like some young kid trying to pretend he was a weather-beaten [folk musician].”
4. He was a difficult student
Another trait that prickled more established musicians was that Dylan sought to learn from them but didn’t want to accept their teachings.
“He was unteachable!” Van Ronk said. “He had to reinvent the wheel all the time. Any number of people tried to show him finger picking of the guitar, but he just seemed to be impervious. He had to work it out for himself, and he did eventually. He became a reasonably good finger picker. But I can’t claim any credit for it. You could almost say he could not acquire anything except by stealing it. That is to say he would watch, and if you tried to explain to him, he would [affect a lack of interest].”
Still, many of the other New York artists couldn’t help but be charmed by Dylan. It wasn’t until he found success that his behavior became less acceptable to them.
