Bob Dylan Worked on a Sitcom With Former 'Seinfeld' Writer

Bob Dylan is one of rock and roll's most mercurial figures; he rarely does interviews and even avoids playing many of his biggest hits in concert. 

And while Dylan may appear humorless to some, that's not the case at all, according to former Seinfeld writer Larry Charles who says he helped Dylan pitch a sitcom to HBO that would have starred the legendary songwriter.

Charles described the experience as "very dreamlike" on a recent episode of comedian Pete Holmes' You Made It Weird podcast

Charles says Dylan had apparently been watching a lot of Jerry Lewis movies while on tour and was inspired to start writing one-liners for a slapstick sitcom (via Ultimate Classic Rock).

Somehow Dylan got Charles' contact information and asked for a meeting in the back of Dylan's boxing gym in Santa Monica.

"He brings out this very ornate beautiful box, like a sorcerer would, and he opens the box and dumps all these pieces of scrap paper on the table," Charles said. 

"Each little piece of paper had a line, like some kind of little line scribbled or a name scribbled – 'Uncle Sweetheart,' or a weird poetic line or an idea or whatever – and he was like, 'I don't know what to do with all this.'"

Charles agreed to help develop the show, if only just for the story. The resulting script sounds about as weird as you might imagine...but still not as weird as the eventual meeting with HBO.

"We wrote this very elaborate treatment for this slapstick comedy which was filled with surrealism and all kinds of things from his songs and stuff," said Charles. "So, we say to Bob, 'If you come to HBO with us, we'll definitely sell the project because they won't have the balls to say no to your face,' and he agrees."

So Dylan went along to meet with HBO. But that didn't mean he was going to try and make anyone feel comfortable. 

Dylan showed up to the meeting in all black wearing a cowboy hat, duster and boots; he spent the entire meeting staring out of the office window.

And just like Charles said it would, the show was sold at the meeting. He and their two managers were elated.

But in case the whole thing wasn't Dylan-y enough, Charles says that on the way to the elevator "Bob says, 'I don't want to do it anymore...It's too slapsticky.'"

And Dylan was out.

Charles had gone too far down the road just to give up like that. He says he redeveloped their script into a movie, which became the 2003 drama Masked and Anonymous, which he directed, starring Jeff Bridges, Penelope Cruz, John Goodman, Jessica Lange and Luke Wilson.   

Photo: Getty Images

Ken Dashow

Ken Dashow

Listen to Ken Dashow everyday and don't forget about Breakfast With The Beatles every Sunday Morning. Read more


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