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Though they both had reputations for their prickliness, Bob Dylan and David Crosby got along. Crosby got to know Dylan when The Byrds covered “Mr. Tambourine Man” in the 1960s, and they maintained a friendly relationship. While Crosby liked and admired Dylan, he admitted that he was challenging to get to know. He believed that Dylan liked being a mystery to others.

David Crosby and Bob Dylan play guitar and sing into the same microphone.
David Crosby and Bob Dylan | Jeff Kravitz/FilmMagic, Inc

Bob Dylan said David Crosby was a ‘colorful’ character

Crosby has feuded with many of his friends and collaborators over the years, and Dylan recognized that he could be unpredictable. Still, he liked him.

“Crosby was a colorful and unpredictable character, wore a Mandrake the Magician cape, didn’t get along with too many people and had a beautiful voice — an architect of harmony. He was tottering on the brink of death even then and could freak out a whole city block all by himself, but I liked him a lot,” Dylan wrote in his book Chronicles: Volume One, adding, “He was out of place in The Byrds. He could be an obstreperous companion.”

David Crosby said Bob Dylan was hard to get to know

Though Crosby had known Dylan for years, he had a hard time getting close to the musician. Dylan deliberately kept people at a distance and was unwilling to offer up much personal information.

“He’s friendly, but he’s not out front. He doesn’t let you in,” Crosby told Stereogum. “You’ll say, ‘Bob, where do you live?’ And he’ll say, ‘Well, you’re looking at a man that has no home.’ He’d be telling you about life instead of telling you he lived in Malibu. He’s not an easy guy. To this day, he’s not an easy guy.”

Though Dylan has been famous for decades, he maintains an air of mystery about him. Crosby said he is this way with friends too.

“He doesn’t welcome you in with open arms and show you who Bob is,” he said, adding, “He likes being mysterious. He likes being oblique. And he’s smart enough to pull it off. He’s a very interesting guy to be friends with. Very interesting.”

The ‘Tangled Up in Blue’ singer reportedly lives an isolated life

One of Dylan’s childhood friends got to know Dylan closely in their years of friendship. He said Dylan is different in private than he is publicly,

“I would say Larry and I were his best friends, sure,” his friend Louis Kemp said in the book Down the Highway by Howard Sounes. “My friend is Bobby Zimmerman, and I don’t relate to him as Bob Dylan — that professional persona … I was never a fan. I was a friend of Bobby Zimmerman, and that’s a whole different relationship from what most people have.”

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Kemp and Dylan had a falling out in 2001 and did not remain in close contact. According to Kemp, this is typical for Dylan.

“Most of the people around him are employees,” Kemp said.