Bob Dylan Worked Closely With a ‘Seinfeld’ Writer on a Widely-Panned Film
In the 1990s, Seinfeld writer Larry Charles learned that his cousin was Bob Dylan’s manager. Eventually, this led to a meeting between Charles and Dylan and a feature film in 2003. Charles directed the film, Masked and Anonymous, and Dylan starred in it, but they worked closely together through the writing process. The film was an overall flop, but Charles said he enjoyed the process of writing with Dylan.
Bob Dylan teamed up with a ‘Seinfeld’ writer to write a movie
Once Dylan and Charles decided to partner up, they spent much of their time writing together. Charles was a writer on Seinfeld and Mad About You, so he had plenty of experience working on scripts. Dylan had primarily written songs at this point, but he enthusiastically threw himself into writing a screenplay.
“I spent a solid two years in a cubicle with him writing,” Charles told Uproxx in 2023. “I mean, he had unending energy. We would write sometimes for 12 hours a day — writing, talking, working things out, not necessarily always scribbling.”
They followed Dylan’s writing style, using scraps of paper with words and phrases on them to put a story together.
“I realized that’s how he writes his songs, he just has these scraps and he slowly synthesizes them into this new thing,” Charles said. “That’s what we started doing with the screenplay.”
‘Masked and Anonymous’ did not do well with critics
Despite the talent of both writers, Masked and Anonymous did not do well with critics. Charles said this was a disappointment that completely derailed his career plans.
“Well, it was my first movie and I thought it was great,” he said, adding, “I really was very proud of it. I thought it was an epic, and I still do. So I honestly was shattered by the response. I mean, now I can laugh about it, but I saw my life going in a certain direction based on that movie and instead I had no movie career whatsoever. It died right there.”
Looking back, though, Charles said it was fitting that the film initially did poorly but has grown in popularity amongst Dylan fans.
“The thing about him is he’s had public humiliation, he’s had failure, he’s had it all and he’s still here,” Charles said. “That’s one of his greatest lessons. He was like, ‘It really doesn’t matter, you just have to keep doing it.’ And he’s very unpretentious about that aspect of it.”
Bob Dylan taught the accomplished writer a great deal
Despite the negative response, Charles said that making Masked and Anonymous was a valuable experience. He learned a great deal from Dylan.
“Not just the shooting of the movie, but the writing of the movie, and just being with Bob Dylan every day for a couple of years, and being able to pick his brain and hear him think and laugh with him,” he said. “He really was like an inadvertent guru to me. It wasn’t like he set out to share wisdom, but he was just spewing wisdom through his very being, and I was lucky enough to be exposed to that.”
