Bob Dylan's "most foolish" move

Does "Masked And Anonymous" look into our future?

Unlike his character “John Wesley Harding” who “was never known to make a foolish move,” the author of that line, a Mr. Bob Dylan, made plenty of ‘em. Historically speaking, the first truly foolish move he made was the album “Self-Portrait,” a record so shoddy and strange, it prompted one of the very few dead-on record reviews that was contained in a single sentence.

“What is this shit?” Greil Marcus famously asked and he spoke for thousands if not millions of Bob Dylan fans, who wondered the very same thing. It was such a swing and miss that years later, Dylan not only revised and reconsidered the record and even got Greil Marcus to do a new batch of Liner Notes. Marcus did not apologize.

Bob Dylan’s most foolish move? Making “Masked And Anonymous”

There were many candidates for the second foolish thing, Some would say Dylan’s divisive move into religious rock with the Jesus-oriented albums “Slow Train Comin’” and “Saved.” Some might grant him that — he certainly seemed sincere about his immersion in the New Testament — and instead point a crooked finger at his mercifully brief mumblin’, stumblin’ tour with the Grateful Dead. Or at the Arthur Baker-cluttered “Empire Burlesque” which might have had a few fine songs, it was hard to hear them through all the noise.

Or they might select from what seemed like an endless, “can’t shut him up” series of cover song albums, many tunes originally done by Frank Sinatra. There was so much of it and the tunes wouldn’t stop coming, the record company finally combined three of them into “Triplicate,” which more resembled a Bob Dylan karaoke night for people who actually remembered what these tunes sounded like before they were put into the sausage grinder of Dylan’s larynx.

Or was it “Renaldo And Clara”? Tough call

But if those were your choices, I would submit you’re all wrong. Considering his flawed and costly experiment with film to this point — “Eat The Document,” “Renaldo and Clara” and “Hearts Of Fire” — you might think Bob couldn’t possibly want to do another film.

He did though, lovingly called it “Masked And Anonymous” ( talk about tipping your hand) wrote it himself, acted in it (well, sorta) and even had a scene where he was

supposed to cry. (Wonder if to generate the tears, all they had to do was show him the box office numbers OR the reviews.)

When the ads said “a film experience not like any other,” for once, that wasn’t false advertising. And Dylan was in fine form. Just as he was in “Hearts of Fire” - a B movie if there ever was one. When a British journalist laid out a long, mind-bending series of questions, then asked Dylan if he wouldn’t be bored on a film set?

“No,” Dylan sneered. “Maybe you’ll be there.”

So with “Masked And Anonymous” that brings us to motive. Why would such an accomplished artist do such a thing? Glad you asked.

According to Larry Charles’ a part-time writer/director of the action, who formerly worked on “Seinfeld” said it all started with a box.

“Bob had a box. A beautiful ornate box, “ Charles said. “One day, he opened it for me. Inside were dozens and dozens of scraps of paper. Piles of them. And on each was something handwritten.”

One day, Dylan dumped the contents of the box onto the desk and said “I don’t know what to do with this.” (Neither did Charles.) So Charles started to look at them.

“I began to sort through the scraps. They were mainly remnants of hotel stationery from around the world…” (Charles was excited. How wild is this!) “I was collaborating with Bob Dylan on whatever! I’m on the Bob Dylan Train and I’m not getting off ‘till the last stop.”

And Charles, who had worked on “Seinfeld” knew the next step. To do a movie, you need a script. That’s where Bob’s box came in once again. Charles began to read those slips carefully.

“Some were aphorisms. Some were non-sequiturs. Some had a name scribbled on them like “Uncle Sweetheart. I would pick up one scrap and say, “Well, the character can be named Uncle Sweetheart” and I’d pick up another “And he may say this.”

“Bob seemed amazed. “You can do that?” he asked me.

“Why not,” I responded….Bob drew from an eclectic reservoir of experience. And had solved the problem of what Harold Bloom called “the anxiety of influence” that most artists suffer from.” Bob Dylan, as we all know, lived in a world of his own. And so, they wrote a script and ended up with a film that did to regular film goers what Lou Reed’s “Metal Machine Music” or Neil Young’s “Arc” did to fans of their respective music.

While film critics and the average viewer would agree it made more sense than Young’s first film “Journey Through The Past,” — which is definitely damning with faint praise — considering the considerable acting talent on hand - John Goodman, Jessica Lange, Luke Wilson, Jeff Bridges, etc., it was a missed opportunity.

Yet there was something about what Dylan and Charles concocted in that bizarre film that, in 2025, seemed eerily prescient. The old dictator President dies (Bob has the tears in that scene) and his stepson takes over this seedy world. As Jack Fate (Dylan’s role) can only watch. And wince.

“There will be no more violence from the organized media,” newly named President Mickey Rourke announces, sounding scarily like what we might hear from 1600 Pennsylvania any one of these days. “Real actual violence will take the place of manufactured violence. We will empty the prisons and we will build the football stadiums and the evildoers from the prisons will be trampled by wild elephants, mauled by uncaged bears and pecked to death by screaming eagles.” (Instead of the current method - deportation, you gather.)

Watching “Masked And Anonymous” now, remembering this is Bob and Larry Charles writing this in 2003, 22 years ago, it’s crazy to think this long walk off a short pier, this pipedream, this whacked out vision hints at what we’re seeing right now in our country, in 2025?

What we have before us now — a self-obsessed, would-be dictator wanting to control everything, the same thing we see Edmund do when takes over after the dictator’s (and father’s) death.

Edmund immediately begins shutting down all sorts of media (NPR, Voice of America) turning things upside down, which is not that unlike someone suing TV stations or yanking the FCC’s chain hard enough to get Stephen Colbert and Jimmy Kimmel off the air. Beware all those who dare to criticize him, shipping people out of this country on a whim, ignoring the Constitution, doing what he damn well pleases. Sound familiar?

How did Bob Dylan project all this with George Bush 43 in the White House in 2003, long before we were subjected to the Donald Trump Experience which didn’t arrive until many years later? Was it just a lucky guess by Bob, unlucky for the rest of us? Was that what was contained in that box?

To think all this happened because for a while, Bob turned his ever-fertile brain to writing fortune cookie messages, creating characters, throwing out lines, non-sequiturs, bad jokes, getting a few lucky bounces along the way. And it became a movie. You can watch it. Really. It came out. Is he done with film? Or does he see worse things in our future?

You wonder if Bob is still filling up that box? There’s certainly no shortage of weird, inexplicable things going on. A week with Donald Trump alone would seem to give Bob enough material to fill that box once more. But a movie? Let’s leave the movies to Bruce Springsteen. Please, Bob.

JOHN NOGOWSKI IS THE AUTHOR OF “BOB DYLAN: A DESCRIPTIVE, CRITICAL DISCOGRAPHY AND FILMOGRAPHY, 1961-2022,” AVAILABLE LOCALLY AT BARNES & NOBLE AND BOOKS A MILLION. ALSO AVAILABLE ONLINE WITH AMAZON.

THIS EDITION INCLUDES MY TWO PREVIOUS EDITIONS, A BRAND NEW INTRODUCTION, A NEW ANNOTATED BIBLIOGRAPHY AND REVIEWS OF BOOTLEG ALBUMS, 332 PAGES OF DYLAN LORE.