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To the public, Bob Dylan is an enigma, but the musicians who know him well say he has a solid sense of humor. Dylan takes his music seriously, but he also brings humor on stage and into the recording studio. He also likes to mess with the artists working with him. Here are three artists Dylan has purposely tried to throw off while playing together and their reactions. 

A black and white picture of Bob Dylan, one of the biggest musicians of the 1960s, wearing a suit jacket.
Bob Dylan | Evening Standard/Getty Images

Bucky Baxter: Bob Dylan embarrassed 1 of his backing musicians

Guitarist Bucky Baxter joined Dylan on tour in the 1990s. Just before playing a song, Dylan abruptly told Baxter to switch instruments.

“One night around that time, at Hammersmith, he was about to go into [his 1963 classic] ‘Don’t Think Twice, It’s Alright,’” Baxter told GQ. “He said, ‘Hey, Bucky! Play mandolin on this.’ I am not really a mandolin player; I could only play in certain keys.”

Baxter tried his best, but Dylan stopped him in the middle of a song to tease him in front of the audience.

“Halfway through, he stops the band, turns to the audience and points to me,” Baxter said. “He says: ‘He isn’t playing, he’s miming.’ And then: ‘Should I fire him?’ The whole audience yells, ‘Yeah!’”

Afterward, an angry Baxter confronted Dylan, who was unperturbed.

“I went to see him afterwards. I was really pissed off,” Baxter said. “He said: ‘Forget it — I was just foolin’ with ya.'”

George Harrison: Bob Dylan rushed him through recording

In 1989, Dylan was recording with former Beatle George Harrison and decided to pull a similar prank. Harrison told producer Don Was not to let him get away with it.

“Bob’s messing with him,” Was said on Southern Accents Radio, per Yahoo. “He moves the engineer, Ed Cherney, out of the seat, and he sits in the engineer’s chair. He’s working the remote control. George Harrison says, ‘Don’t let him do what he did to me last time, which is he just recorded me one take, and that was it. I didn’t get to fix the thing.’ I said, ‘Okay. Yeah. Sure. No problem.’”

Dylan heard Harrison say this and rushed him into the song with little instruction.

“Bob, of course, hears that, and he’s going to do the same thing,” Was said. “George hasn’t even had a chance to tune up or to hear the song. He doesn’t even know what key it’s in. Bob fast forwards to the solo and is like, ‘Go.’ He hits it into record. George figures out what key it’s in.”

Though Dylan would have kept the imperfect solo, Was and Harrison convinced him to try another take.

Tom Petty and the Heartbreakers: Bob Dylan’s spontaneity was beneficial for the musicians

In 1986, Tom Petty and the Heartbreakers joined Dylan on tour. Dylan tossed them into songs with little warning and expected them to keep up with his improvisations. Unlike Baxter and Harrison, though, Petty saw this as a learning opportunity.

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“I learned so much from Bob Dylan,” he told The Daily Telegraph in 2012. “He gave us a kind of courage that we never had, to learn something quickly and go out on stage and play it. You had to be pretty versatile because arrangements could change, keys might change, there’s just no way of knowing exactly what he wants to do each night. You really learned the value of spontaneity, of how a moment that is real in a concert is worth so much more than one you plan out.”