Bob Dylan’s Road Manager Said the Musician Was ‘Miserable as F***’

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.

“He wasn’t like that later on,” Maymudes said, per the book Down the Highway by Howard Sounes. “The success, the power that he engendered through the years, made him [bolder].”

Bob Dylan’s road manager admitted that success also made him miserable

Success also grated at Dylan’s nerves. Though he loves music, the privacy he values became harder and harder to maintain with fame. Dylan’s defense mechanisms don’t do much to endear him to the people around him.

“Does he have any compassion?” Maymudes said. “Questionable.”

Dylan also rarely saw anyone outside of the people who worked with him, something one of his childhood friends also noted.

“He does not see people regularly,” Maymudes said. “He is not a friendly guy.”

Maymudes also said that Dylan never seemed to grow comfortable with his success.

“He’s crankier now by far,” Maymudes said ahead of Dylan’s 60th birthday. “No, he’s miserable. He’s miserable as f***. He’s doing the best he can with his life. He is forced to live a weird kind of life because of the impact he’s had. All his fears and phobias are enlarged by success. It didn’t help him overcome them, it made everything worse.”

His privacy has kept him in the music industry for decades

For someone who doesn’t like his chosen field, Dylan remains exceptionally involved in it. With the exception of a pause during the coronavirus (COVID-19) pandemic, Dylan has toured without stopping since the 1980s. He loves music, just not the fame that comes with it.

Dylan has been able to continue working as a musician because of his dedication to his privacy. He has given many interviews over the years but avoids discussing anything too personal, like his romantic relationships, home life, and friendships. As Maymudes said, though, he isn’t close to many other people, which is likely at least partly intentional on Dylan’s part.

Dylan’s childhood friend, Louis Kemp, said the musician handles his private life better than any other celebrity he’s seen.

“He doesn’t like to bring his family into [the public eye],” Kemp said, adding, “He has always kept it private, as much for their protection as anything. He figured out how to deal with it all better than anybody else I have ever seen who became famous.”

If Dylan hadn’t figured out a balance between his private and public life, he might have retired years ago.