'Masked and Anonymous' at 20: Bob Dylan's Most Insane Movie Role | Features | LIVING LIFE FEARLESS

‘Masked and Anonymous’ at 20: Bob Dylan’s Most Insane Movie Role 

In the summer of 2003, Bob Dylan starred in an extremely bizarre film called Masked and Anonymous, in which he played a rock star named Jack Fate. In the film, set in a probably post-apocalyptic version of the United States, Fate is the son of the dying president/dictator, sprung from prison in order to plan a benefit concert. 

But he also looks and sings very similar to Bob Dylan, and his iconography and Dylan’s have much in common. So he’s sort of Bob Dylan, and sort of not. (And also, he appears to be a Christ figure.) 

“He’s an icon and he delivers an icon’s performance, literally,” Keith Phipps wrote for the AV Club at the time, of Dylan in the film. “He could easily have been replaced by a piece of wood with his face painted on it.” And you thought Bob’s turn in Pat Garrett and Billy the Kid was strange… 

The trailer, for one thing, makes Masked and Anonymous look a lot more like a normal movie than it actually is:

I described Masked and Anonymous, in my original review, as “a melange of post-apocalyptic nonsense and celebrity cameos and was one of the most critically ravaged 2003 films this side of Gigli.” 

The “Plot”

Indeed, the plot makes little sense, and the film seems to have little going for it besides Dylan ambling around and occasionally having encounters with people played by famous actors. 

In Masked and Anonymous, he repeatedly crosses paths with famous actors of the time, including both stars of The Big Lebowski (Jeff Bridges and John Goodman), along with Penelope Cruz, Val Kilmer, Jessica Lange, Mickey Rourke, Christian Slater, Giovanni Ribisi, Luke Wilson, Bruce Dern, Ed Harris and Cheech Marin. The film’s structure is unusually heavy on the famous actors showing up, delivering a long monologue, and then instantly leaving, often via a fatal gunshot. 

At least the characters all have cool names. Goodman is “Uncle Sweetheart.” Lange is “Nina Veronica,” and Cruz is “Pagan Lace.” Even Dylan and Charles co-wrote the script under the pseudonyms “Sergei Petrov” and “Rene Fontaine.” 

I’ve always argued that Bob Dylan is a lot funnier than he’s often given credit for, and Masked and Anonymous is one of the funniest things he’s ever done, although exactly how intentional the comedy is a separate question. 

Masked and Anonymous was directed by Larry Charles, the veteran Seinfeld and Curb Your Enthusiasm hand who later directed Borat and Bruno, as well as a fantastic but little-seen Netflix documentary series called Larry Charles’ Dangerous World of Comedy, in which he interviewed the likes of the Liberian warlord known as General Butt Naked. 

I’m Not There, directed by Todd Haynes and released in 2007, was the “official” Bob Dylan biopic, even though it was just as weird and unconventional, including the part where eight different performers portrayed Bob (Cate Blanchett was the most convincing). That movie was certainly more acclaimed than Masked and Anonymous. But in the years since, I’ve certainly thought about Masked and Anonymous more. 

It’s also left a legacy. In 2018, Neil Young starred in a film for Netflix called Paradox, which appeared to be a spiritual remake/sequel to Masked and Anonymous. including a similarly baffling performance by the lead singer/actor. 

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