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Bob Dylan has been a celebrated musician for decades, but some of his projects have been unsuccessful. Dylan has been touring for the better part of the past 40 years, but according to his friend George Harrison, he’s always looking for a job outside of the music industry. He’s tried a number of different projects. Here are five that didn’t work out for him.

Bob Dylan stands at a podium with a pile of papers.
Bob Dylan | Lester Cohen/WireImage

A fight over an unsuccessful coffee shop ruined one of Bob Dylan’s friendships 

Bob Dylan and his tour manager, Victor Maymudes, opened a Santa Monica coffee shop together. Maymudes made his daughter, Aerie, a manager, and they decided to rely on word-of-mouth promotion instead of advertising that a celebrity-owned the business. As a result, it began to lose money.

“It was wonderful except for the simple fact that it was still empty and bleeding money with every cappuccino given to the members of the private and exclusive hidden gym,” Maymudes’ son Jake wrote in the book Another Side of Bob Dylan. “Was it my sister’s fault that the coffee shop on paper was a financial failure? Absolutely, of course it was. Was it Bob and Victor’s lack of oversight and management that fueled Aerie’s lack of experience and her inability to curb the downward financial spiral of the cafe? Absolutely.”

The cafe’s failure enraged Dylan, and he violently fired Aerie as the manager.

“My father fought back in defense of Aerie’s unjust treatment, not out of denial of the facts but because of Bob’s sheer abandonment of respect for her,” Jake explained. “Her removal from management of the cafe may have been warranted, but the way it was done was unforgivable.”

As a result of the business, Dylan and Maymudes’ relationship broke apart, and they never reconciled.

The musician’s satire magazine was panned by critics

On top of being a musician, Dylan has also dabbled in visual art. He has welded sculptures and painted, but not all of his pieces have been well received. In 2012, he exhibited some of his work at the Gagosian Gallery in New York. Many of these pieces were Dylan’s creative takes on magazine covers.

“In any event, for his latest efforts Mr. Dylan takes the covers of old copies of Time, Life, Rolling Stone, Playboy and less prominent magazines and tinkers with images, cover lines and much else, in what look like lame endeavors at satire,” The New York Times wrote, adding, “With the alterations ranging from obvious to juvenile to obscure, and the anonymous, deeply familiar format, there is little incentive, visually or intellectually, to remain engaged. The line between naïveté and cynicism is sometimes very thin.”

Bob Dylan sought help for a cologne brand that never made it off the ground

In the late 1980s, Carrie Fisher received a surprise phone call from Dylan. A cologne company had asked him to endorse a cologne called Just Like a Woman. Dylan didn’t like the name, so he asked Fisher for suggestions.

“Do I look like someone who would be wandering around with a bunch of cologne names rattling around in my head?” she wrote in her book Wishful Drinking. “Well, tragically, I did. I did have quite a few ideas for cologne names and so I told them to Bob. There was Ambivalence, for the scent of confusion. Arbitrary for the man who doesn’t give a s*** how he smells! And Empathy — feel like them and smell like this.”

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Dylan liked her suggestions and even pitched a new business venture.

“Well, Bob actually liked those!” Fisher wrote. “And then he said he thought he might like to open a beauty salon, and I said, ‘What? Like Tangled Up and Blown?'”

Ultimately, though, Dylan never had his own cologne brand or beauty salon. 

Bob Dylan was the reason his TV show was unsuccessful 

Dylan almost had a huge success with a slapstick comedy series he developed with writer Larry Charles. They pitched the project to HBO’s president, who greenlit it. Dylan made sure it never saw the light of day, though.

“We go out to the elevator — Bob’s manager Jeff, my manager Gavin, me and Bob – the three of us are elated we actually sold the project and Bob says, ‘I don’t want to do it anymore. It’s too slapsticky,'” Charles said on the podcast You Make It Weird, per Rolling Stone. “He’s not into it. That’s over. The slapstick phase has officially ended.”

It could have been a success, but Dylan didn’t let it get that far.