Bob Dylan Created and Nearly Starred in a ‘Slapstick’ HBO Show, but Quickly Abandoned It

Bob Dylan is revered for his songwriting abilities and his capacity to command an audience during a show. In the 1990s, he tried his hand at a different kind of writing and showmanship. Working with veteran TV writer and producer Larry Charles, Dylan created a slapstick comedy series that the pair pitched to HBO. Dylan would star in the project. As soon as success seemed like a possibility, though, Dylan abandoned the series.

Bob Dylan plays guitar and sings into a microphone during a show in 1991.
Bob Dylan | Michael Putland/Getty Images

Bob Dylan met with comedy writer Larry Charles to work on a show

Charles, who has worked on Seinfeld and Borat, spoke about the time that he teamed up with Dylan to create a comedy series.

“He’d gotten deeply into Jerry Lewis, and he wanted to make a slapstick comedy,” Charles said on the podcast You Make It Weird, per Rolling Stone. Dylan also “wanted to star in it, almost like a Buster Keaton or something.”

They first met at the back of a boxing gym Dylan owned. Dylan’s assistant offered to get them drinks, and Charles ordered an iced coffee while Dylan asked for a warm drink.

“So they bring a hot coffee for him, like a cappuccino, and they bring the ice coffee for me, and they put them together in the middle of the table, and he immediately grabs my ice coffee and starts drinking my ice coffee,” Charles explained. “And I’m watching him drink it, and I’m not touching the other thing. I don’t want the other thing. And finally he almost finishes my drink and he goes, ‘Why aren’t you drinking your drink?’ And I’m like, ‘You’re drinking my drink.’ And he laughed and that broke the ice. It’s like a test. Like, he drank my drink. How would I react?”

It seemed Dylan wanted a partner who would lean into the surrealist world of his proposed comedy.

Bob Dylan and Larry Charles pitched the show to HBO

Charles explained that they wrote the show with a “cut-up technique.” This is also how Dylan writes songs.

“We’d take scraps of paper, put them together, try to make them make sense, try to find the story points within it,” he explained. “And we finally wrote … a very elaborate treatment for this slapstick comedy, which is filled with surrealism and all kinds of things from his songs and stuff.”

Both Charles and Dylan attended the pitch meeting at HBO.

“I probably was having a nervous breakdown and didn’t realize it, but I wore pajamas everywhere I went,” Charles said. “I was so comfortable. It was great. [Bob] shows up for the meeting at HBO in a black cowboy hat, a black floor-length duster, black boots. He looks like Cat Ballou or something. He looks like a Western guy who’s carrying six guns.”

Dylan wasn’t much help in the meeting, though. While Charles pitched the series, the musician stared absently out the window. Still, HBO’s president greenlit the project. Ultimately, though, the series never came to fruition.

“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 explained. “He’s not into it. That’s over. The slapstick phase has officially ended.”

The singer has worked as an actor

The abrupt end to the comedy series did not mark the last time Charles and Dylan worked together. They wrote the 2003 film Masked and Anonymous, in which Dylan starred as a rock star set to put on a benefit concert.

Before this, Dylan starred in the 1987 film Hearts of Fire as another musician. In 1973, he had his first dramatic role in Pat Garrett & Billy the Kid, a film for which he created the soundtrack. He also starred in and directed the film Renaldo and Clara alongside his then-wife Sara Dylan. 

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