Bob Dylan wears a cowboy hat and holds a guitar while standing in front of a microphone.

Bob Dylan has been a famous musician for six decades and, according to his road manager, he hasn’t had a good time doing it. Dylan’s longtime road manager, Victor Maymudes, admitted that Dylan doesn’t take much pleasure out of his immense success. He said that over the years, Dylan grew more “miserable.” It seems that his dedication to privacy is what has kept him in the industry at all.

Bob Dylan wears a cowboy hat and holds a guitar while standing in front of a microphone.
Bob Dylan | Harry Scott/Redferns

Bob Dylan’s road manager said success made the musician bolder

Dylan’s first big success came with the release of The Freewheelin’ Bob Dylan in 1963. Though he never liked fame — his collaborator and girlfriend Joan Baez said fans terrified Dylan — Maymudes said that success emboldened the musician. He said that Dylan was extremely timid, even in the early 1960s.

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