Yes, there was a point in time when former Seinfeld writer and current Curb Your Enthusiasm collaborator Larry Charles sold a slapstick comedy series to HBO with the help of Bob Dylan, who wanted to star in it. Charles recounted the surreal event on the You Made It Weird podcast with comedian Pete Holmes recently.
It was the 1990s, and Charles was in-demand having worked on five seasons of the NBC mega-hit Seinfeld. "He'd gotten deeply into Jerry Lewis, and he wanted to make a slapstick comedy," the writer said about Dylan, via Dangerous Minds. Charles ended up meeting with the "Forever Young" singer in Santa Monica, California, saying that the initial brainstorm was an interesting time.
Dylan ordered a regular coffee while Charles opted for an iced coffee. When the beverages arrived, the legendary singer took the iced option. "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?" he said.
The pair used Dylan's method of songwriting to put together a story. According to Charles, the singer brought out a box filled with scraps of paper with ideas and notes on them. He dumped them on his desk and the two fiddled with the papers until they came up with "a very elaborate treatment for this slapstick comedy, which is filled with surrealism and all kinds of things from his songs and stuff."
Dylan and Charles pitched the show to HBO, who in return bought it on the spot. By the time they got to the elevator to leave the building, Dylan had decided he wasn't into it anymore, saying, "I don't want to do it anymore. It's too slapsticky." However, the two would end up working together on 2003's Masked and Anonymous.
There was also a time when Dylan wanted to cut albums with The Beatles and The Rolling Stones.
