Not Dark Yet (but we're getting there)

Is Bob Dylan's 2003 film "Masked And Anonymous" eerily prophetic?

EDITOR’S NOTE: To celebrate my one-year Substack anniversary, I thought I’d take another look at Bob Dylan’s strange 2003 film, “Masked And Anonymous,” wondering if it was as dark and weird as I remembered when I first saw it. Instead, I saw something else, something troubling. Take another look, see what you think…(Available on TUBI)

MASKED AND ANONYMOUS

A film by Larry Charles and Sergei Petrov (Bob Dylan)

Released July 24, 2003

“Masked and Anonymous” or The World As It Occurs To Bob Dylan in 2003.

When Bob Dylan enlisted Larry Charles, a writer on the first five seasons of “Seinfeld,” to help him concoct this fever dream of a film out of the cotton-pickin’ blue in 2003, you might have expected Seinfeldian, observational comedy.

Instead, you get a dystopian look at a faded country, apparently ruined by a corrupt dictator who looks at democracy as a nuisance, free speech intolerable, justice just a rumor. While it doesn’t seem possible that Bob Dylan could have seen all this coming, the parallels to where we are – and may soon be -- in 2025 are awfully dark. Is that where we’re headed? Some would say, “Yes.”

Released in 2003, Bob Dylan's "Masked And Anonymous" seemed awfully dark and pessimistic. It looks different now.

Filmed over 20 days in muted colors and shot on as downtrodden a set as you’re likely to see – the film was made in between Dylan’s “Never Ending Tour” dates -- you wouldn’t have expected the Dylan and Charles combination to depict the United States of 2003, halfway through George Bush 43’s first term, as this fading, out-of-control third-world country, a cruel, mean-spirited place run by a dying dictator, with corruption from, as Dylan once sang, “from stern to bow.” But that’s what we get.

In “Masked and Anonymous,” there’s death in the streets, hardly anybody seems worthy of trust or respect, nobody is smiling or seems happy, everybody is just living out their days wondering when the next hammer will drop or the next bullet will take them.

Throughout the film, we hear and usually recognize Dylan’s songs but they’re often performed in foreign tongues. It’s as if language should be no barrier to their significance, Bob’s words know no boundaries and have already crossed the globe (which, of course, they have.) And yes, it surprising to hear these familiar tunes in different languages.

We also get to hear, in original form, the very beginning of “Like A Rolling Stone” and much of “Not Dark Yet” from “Time Out Of Mind” and also a moving clip of his originally discarded brilliant track, “Blind Willie McTell.” That song happens to be playing as we see Dylan, as Jack Fate, riding a ramshackle bus through the worst part of Los Angeles. When we hear him sing “this land is condemned,” and we look out the window at the ugliness around him, he seems prophetic. And that isn’t the only time.

Throughout the one hour and 46 minute film, there are nudges, hints, references to all-things Dylan, like a building named “The Midas Judas Building” or the titles of the programming on network TV being the names of Dylan songs. He’s left plenty for the Dylanologists.

The plot, if we can call it that, suggests that Dylan, as Jack Fate, is being let out of prison to perform a benefit concert promoted by a grossly overweight and a tastelessly frilly shirted John Goodman (Uncle Sweetheart) with chain-smoking former temptress Jessica Lange (Nina Veronica) alongside as the network go-between.

The network, run by a bunch of what seems to be perpetually displeased African-Americans, doesn’t seem to be particularly interested in Fate or his music one bit. But Goodman, a fast-talking scammer, is proceeding as if they do.

We never find out why Fate is in prison but as things unfold, it may have something to do with him messing around with his father’s mistress, Angela Bassett. Before Fate and his dying Dad’s big scene, which occurs a ways into the film after we see Dylan apparently atone for his sins by climbing a hill and visiting a religious-like grotto, we do get to see him sing and play a few tunes. He’s frighteningly skinny, sports a Vincent Price mustache and runs through a few songs, not his hits, of course.

We hear “Down In The Flood,” “Diamond Joe,” “Dixie,” (really!) and then we hear “I’ll Remember You” interspersed with scenes with Goodman, Lange and others putting the theoretical show together. Why those songs?

After “Dixie,” and a rousing cheer from the audience, (why is Bob playing a Civil War song? Is he predicting something?) Fate/Dylan has a quick confab with Sweetheart who explains that the network had some requests.

This is an inside joke, of course, because we know that one thing Bob Dylan does not and never will do is take requests. But Sweetheart lays them out: The Beatles’ slow “Revolution” and The Who’s “Won’t Get Fooled Again” and the Stones’ “Street Fighting Man” and the Coasters’ “Cell Block Number Nine” and Neil Young’s “Ohio” and (laughably) Barry McGuire’s “Eve Of Destruction” and finally, the MC5’s “Kick Out The Jams.” All “protest” songs.

“Sounds like a lot of songs,” Fate says, flatly. Sweetheart says he’s trying to rebuild Fate’s career. Don’t think that’s the way to do it.

Then, Fate is told that a journalist wants to meet him, Uncle Sweetheart thinks they can use the publicity and as we hear Fate drift into a soulful “I’ll Remember You,” some strange things start to happen.

We cut to Nina Veronica apparently having a moment of self-pleasure as the song plays while she’s in an open window, in full view of a sea of small tents and people walking around, then we get a cutaway shot of the dictator/Fate’s dad dying. After the emotional song concludes, journalist Tom Friend (Jeff Bridges) starts his inane questioning of Fate, who – as Bob Dylan – has heard it all before.

First, we get an Elvis reference. “Well, I know you had a twin brother,” Friend says, referring to Elvis’s dead twin, not Dylan.

Fate doesn’t miss a beat, tells him he never came back from a hunting trip which doesn’t go over well. It looks like the interview is over but Sweetheart, pushing for the publicity, keeps it going. Friend gets even weirder.

“Mothers of Invention, Jack, Zappa?” he asks. “Now, there’s a guy who wouldn’t take no for an answer.” Obviously, this has nothing to do with Fate/Dylan and it’s clear that Bob’s lampooning of the press has just started. They’re rude, they have an agenda and they ask ridiculous questions. And Friend (obviously an ironic handle) continues.

“You know that singer in the group the Bee Gees, he sounds a lot like Gene Pitney, doesn’t he?”

Fate counters. “As opposed to who?”

“Town Without Pity. You remember that, Jack? The place where they’d lock you up for doing something you haven’t even thought about doing yet?”

This may be foreshadowing, hinting at Jack’s time in jail and where this whole film is headed. Then Friend goes even further

“What about (Jimi) Hendrix at Woodstock?” he asks and of course, everybody knows Bob made it a point to MISS Woodstock, even if it was just a few miles from his home. In “Chronicles, Vol. 1” which came out the next year, he makes his disdain for that spectacle very clear.

“You weren’t there at Woodstock? Why?..Playing “Star-Spangled Banner” through two lousy speakers to a half million people in the mud…What was he saying, Jack? Revolution? I don’t think so. You could hear tears in every note he played, saying ‘Love me, love me. I’m not a traitor, I’m a native son…one sad cry of pity in a town without pity…”

So much for the probing questions from the journalist.

After this improbable run of non-sequiturs and the sort of journalist questions that must have rung in Bob’s head for years on end, we get a moment of absolute clarity. It jumps off the screen as a 10-year-old African American girl named Tinashe Kachingwe and her mom walk up to Fate as Mom explains that she’s made her daughter memorize his songs. The little girl breaks into a lovely acapella version of “The Times Are A-Changin’.”

We hear a little of it, then Fate/Bob interrupts and begins a narration of a flashback which appears to be him being caught with the mistress, perhaps explaining why his father put him in jail. At the end of the clip, Fate adds: “All of us in some way are trying to kill time. When it’s all said and done, time ends up killing us.”

Oh.

We cut back to the girl, she finishes the song, everyone claps and it’s interesting that Fate has no reaction. It’s as if this classic song, which put him on a national stage, came from somebody else in another time. It seems very far away.

As for the movie, it’s apparent there seems to be some sort of tangled web between Fate and his father, who is dying. Fate calls his room once, then hangs up. When he finally gets to the mistress Bassett, she says she wondered if he’d ever return, then asks if he’s resolved things with this father. He says no.

Then it’s time for Bob to act. Really. Bob Dylan as Jack Fate as an actor. It was a step up. In his previous films “Eat The Document” and “Renaldo and Clara,” he’s just being Bob Dylan. Essentially being his inscrutable self and letting the camera run.

Here, playing the role of Jack Fate, he has set himself up with another task. He must pretend he’s sad at the imminent death of the father who apparently imprisoned him. Bassett kicks it off, wondering why Fate shows up at her place, after getting out of jail, visiting the religious grotto?

“Then what you coming back for, Jack?” she asks. The two sit on the edge of the bed that, evidently, he remembers well.

“I got to see him,” Dylan says as sincerely as his poker face will let him. “I’m tired of not seeing him. I want him to see me.”

Then Bassett, perhaps speaking as if she were voicing what Bob Dylan might want to hear his devoted fans to say to him – “You gave it all away, didn’t you? You gave all the best of you away.” Remember that album title: “Good As I Been To You”?

Dylan, as Fate, responds, “Yeah, I did. I gave it all away to them sons of bitches, either unwilling or unable to accept it.”

“We all did,” Bassett says. Fate doesn’t respond, looks down at the floor.

“You want to go see him, you’d better go now. I hope it’s not too late.”

Then, after a few words, she says, “I want to do something for you. What can I do?” She leans into Fate’s inscrutable face in a near-kiss. Fate’s expression doesn’t change. Is he acting? Or is this the real Bob in 2003, emotionally unavailable?

Fate goes to visit the dying old man but first, runs into Edmund (Mickey Rourke), his estranged half-brother, waiting to take over the country. He tells Fate “I’m the man your father always wanted you to be. I’m the next president of this country.”

Rourke then offers a bit of Dylan-flavored prophecy: “When inferior people want to revolt, they do. When they become equal, they want to be superior. You’re looking at the top man now, Jack. This ain’t no dog and pony show.”

In his big scene, Fate (Dylan) walks in, hat in hand and sits on the side of his ailing father’s bed as the song “Senor” plays in the background. Fate’s father turns to see his son’s face and we hear the line “This place don’t make sense to me no more.” The camera swings to Fate in a closeup and yes, friends, he appears to have a tear underneath his left eye and wrinkled brow. The camera stays on him as he looks up to the heavens and when it does, we can see a matched set of tears. There are no words exchanged.

Now, back on the set, there’s talk the concert might be cancelled and journalist Friend starts to get into it with Uncle Sweetheart about losing his “exclusive” with Fate.

This gives the filmmakers a chance to flip back to Fate (Dylan) on stage, who’s playing a rocked-up version of his obscure “Drifter’s Escape” from “John Wesley Harding.” By choosing that song, Fate/Dylan can perhaps vent about what he and his songs have been subject to for years and years.

That song features the lines “My life, it hasn’t been a pleasant one, and my time, it isn’t long. I still don’t know what it was that I’ve done wrong,” Fate, remember, is fresh out of jail. And, well, banging your old man’s girlfriend might be a start.

But before we start thinking too hard about that particular moral dilemma, the film cuts to this absurd scene: a man dressed like Pope John and a man undressed like Gandhi are sitting on either side of Penelope Cruz, journalist Friend’s frequently praying girlfriend and all are listening carefully to Fate. She says “He’s good. He’s great. I love his songs, because they are not precise. They are completely open to interpretation.”

Unlike, say, Scripture?

Then Uncle Sweetheart (Goodman) and Bobby Cupid (Luke Wilson) get their turn to explicate the song. Considering Bob and Larry Charles wrote these lines, they must have had fun with this kind of thing, maybe something Bob always wanted to do.

“You got any idea what that song’s about?” Sweetheart asks.

“Yeah, it’s about trying to get to heaven,” Cupid explains. “You got to know the route before you start out.”

“No, it’s not about that at all,” Sweetheart counters. “What strikes you about the song is the Jekyll and Hyde quality. The song is written from Hyde’s point of view. That’s what you like. It’s about doing evil and trying to kill your conscience if you can. It’s not like those other songs of his, the ones about faithless women and booze and brothels and the cruelty of society. It’s not like those. This one’s right up your alley. It’s about doing good by manipulating the forces of evil. It’s just like you.”

Well, the truth is “Drifter’s Escape” was the last song on Side One of Dylan’s “John Wesley Harding” and it seems to be about injustice, an unfair trial, a guy about to be framed but an act of God, a bolt of lightning, strikes the courthouse. This frightens everyone into kneeling to pray and as they do, the drifter escapes. What would the Pope and Gandhi say about that sort of religious intervention?

Dylan/Charles/Fate are playing with us here. What do his songs mean? Is anyone smart enough to figure them out? Is he saying everyone is wrong? And it’s Bob Dylan doing a movie and he knows what songs people want to hear. So instead, we get “Diamond Joe” and “Dixie”? Or it’s “OK, I’ll give them to you but they’ll be in a foreign language.” His idea of a compromise, I guess.

After a quick cut to Veronica/Lange hearing on the radio that lowering a microphone down into a 30-mile hole in Trenton produces “the sounds of millions of suffering souls,” and “the center of the Earth is hollow,” this sets us up nicely for more of the same sort of whacky stuff from Friend, who catches Fate while he’s shaving for round two of his array of absurd questions, which, we gather, Bob has stored up for years and years. There’s plenty more.

“You’re supposed to have all the answers,” Friend says. “What makes you tick…You think good and bad are irrelevant. Who’s your true companion? …The empire is finished. That’s where you got your start. How does that make you feel?”

The interview/inquisition mercifully ends. Fate splits and runs into a black-faced, banjo-playing Oscar Vogel (Ed Harris) who starts to share bad stuff about his father the dictator. Vogel used to be his father’s favorite (in blackface?) but then he spoke up about what injustices he was seeing.

“He was doing things that were wrong, your father,” Vogel says. “His desire for retaliation and revenge was too strong.” (Gee, who does that sound like? And this was written 22 years ago!)

“I had a show, I had a forum so I spoke out,” Vogel says. Does this echo how Bob felt about his topical songwriting days and why he dropped that kind of political material? Is that why we don’t have any topical songwriting now, fear of retribution?

, Fate says he’s gotta get back to the stage where he goes on to perform the strongest song in the film, “Cold Irons Bound”, the rockingest track from “Time Out Of Mind.” He’s in mid-song when we cut away to half-brother Edmund (Rourke) making the announcement he’s been waiting for. The President has finally died. Now he can make the speech he’s been waiting to deliver.

Edmund begins: “We are rewriting the history books (sound familiar?)…peace that can only be achieved through strength so in my first act as the new president, we will begin immediately to deploy troops in the southern region. We will resume bombing in the jungle.

“There will be no more violence from the organized media,” he continues, 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 deportation, you gather.)

Remember, this is Bob and Larry Charles writing this in 2003, 22 years ago. Is it crazy to think this hints at what we’re seeing right now in our country, in 2025? For what do 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 death. He begins shutting down all sorts of media (NPR, Voice of America) turning things upside down, which is not that unlike someone suing TV stations who dare to criticize him, shipping people out of this country on a whim, ignoring the Constitution, doing what he damn well pleases.

How did Bob Dylan project all this with George Bush 43 in the White House in 2003? Was it just a lucky guess by him, unlucky for all of us? What made Dylan feel he had to share this with us, especially then? Watching the film when it came out, it just seemed dark and quirky and unnecessarily pessimistic. What if he was, uh, right?

As the film winds down, we hear new dictator Edmund continues his spiel: “Furthermore, we will alert the rebel leaders that the negotiations finished. There will be no more compromises, no more concessions, just complete and utter unequivocal surrender. We have learned a valuable lesson. Great nations do not fight small wars. There will be no more stupidity, no more mistakes. It’s a new day.” Maybe like “the greatest first hundred days in the history of our country,” like we just heard about.

We see them pull the sheets over the dead dictator as Fate/Bob rocks on with “Cold Irons Bound.” The song ends, there’s a new leader in charge and all hell breaks loose. Sweetheart and Friend get into it and believe it or not, scrawny ol’ Fate/Bob, of all people, who can’t weigh more than 120 pounds, steps in and breaks it up.

Like Hamlet, which otherwise this does not resemble in the least, this also ends with a death. Fate/Bob threatens Friend with a broken Jack Daniels bottle, Friend pulls a gun, Bobby Cupid comes in and smashes a guitar (supposedly Blind Lemon’s guitar) over Friend’s back and the journalist ends up dying. Which to Bob Dylan probably was what he considered a happy ending.

Bobby Cupid escapes, Fate/Dylan stays behind and is arrested by the militia after Nina Veronica (Lange) frames him for Friend’s death. Fate/Dylan is put in handcuffs and taken away.

Then, as the camera pulls away, we see folks kneeling over the dead body, like the end of Hamlet. Two gendarmes pick up Sweetheart, too and one says “For everything in life you do, Sweetheart, there’s a price. You pay it up front, in the beginning or you pay it at the back end.”

We get an overhead shot of Fate/Bob in handcuffs, going through a doorway then led to a van where he’s driven away. The camera zooms in on his blank, mustachioed face, his eyes in a sort of squint into the lens as his voiceover comes on.

“I was always the singer and maybe no more than that,” Dylan’s voice says. “Sometimes, it’s not enough to know the meaning of things. Sometimes we have to know what things don’t mean as well, like what does it mean to not know what the person you love is capable of? Things fall apart, especially all the neat order of rules and laws. The way we look at the world is the way we really are. See it from a fair garden, everything looks cheerful. Climb to a higher plateau and you’ll see plunder and murder. Truth and beauty are in the eye of the beholder. I stopped trying to figure everything out a long time ago.”

Then Bob’s voice comes on, singing a gentle, recent live performance of his chestnut “Blowin’ In The Wind.”

And as he’s led away, we hear “How many roads must a man walk down before you call him a man?” he sings softly. “How many seas does the white dove sail before she sleeps in the sand? And how many times must the cannonballs fly before they’re forever banned? The answer my friend is blowin’ in the wind. The answer is blowin’ in the wind.”

Maybe this isn’t what he intended but the impression left with the viewer is Bob had a much clearer understanding of life, the world itself, good and evil, when he was starting out, when he was just a kid and wrote songs like “The Times They Are A-Changin’” and “Blowin’ In The Wind.”

He was so much older – and wiser – then. He’s younger than that now. And “Masked And Anonymous,” prophetic or not, sure doesn’t do anything to clear things up.

John Nogowski is the author of "Bob Dylan: A Descriptive, Critical Discography and Filmography, 1961-2022”, 3rd edition. Available on Amazon.