
‘Masked and Anonymous’: The movie Bob Dylan never got right
Some of the best songs that Bob Dylan ever wrote are so cinematic in scope and in their storytelling that they can, at times, feel as visual and as vivid as if you were watching a movie. With sprawling casts of characters, unexpected twists and turns, high drama and grand imagery, songs like ‘Lily, Rosemary and the Jack of Hearts’, ‘Senor (Tales of Yankee Power)’ or ‘Tin Angel’ fit as much action into ten minutes as most movies can fit into 120.
Dylan even once said that he wanted to turn his 1985 song ‘Tight Connection to My Heart (Has Anybody Seen My Love?)’ into a movie. “I want to make a movie out of it,” he commented. “I think it’s going to go past on the way, but of all the songs I’ve ever written, that might be one of the most visual.”
Throughout his career, his songs have been informed by his lifelong love of the cinema, but at that time in the mid-1980s, the impact was particularly evident. Several lines of Humphrey Bogart dialogue from films like The Maltese Falcon, Casablanca and The Big Sleep, among others, turn up in the lyrics to songs across Empire Burlesque, while on his next album, Knocked Out Loaded, he weaves a reminiscence of the 1950 Gregory Peck picture The Gunfighter into his narrative on the epic ‘Brownsville Girl’. Much later, he gave a nod to Leonardo DiCaprio’s performance in Titanic during his long 2012 song about the shipwreck, ‘Tempest’.
He never turned ‘Tight Connection to My Heart’ into a movie, although it does boast a wonderfully zany music video shot by film director Paul Schrader on location in Tokyo, Japan. Still, Dylan has experimented with making movies a couple of times throughout his long career.
Beyond his music, Dylan himself is a magnetic figure. He is captivating and charismatic to watch. Whether it is on stage or on screen, you can’t take your eyes off him, but his forays into theatrical film have never been too well received. The revolutionary documentary of his final all-acoustic tour in 1965, Dont Look Back, was a groundbreaking exercise in the way that musicians were presented on film and led to the birth of the cinéma vérité genre, but its follow-up Eat the Document was never widely enjoyed or distributed.

In 1973, Dylan made his (movie) acting debut as Alias in Sam Peckinpah’s Pat Garratt & Billy the Kid, but his part was not big enough to warrant too much attention (though the soundtrack did spawn the timeless ‘Knockin’ on Heaven’s Door’).
The first feature-length film he wrote, recorded, edited, and released himself, Renaldo and Clara, from 1978, was dismissed as overlong and self-indulgent at the time and has never been re-released or re-appraised. Hearts of Fire suffered a similar fate in 1986, as did his greatest cinematic achievement, Masked and Anonymous.
Released in 2003, and featuring an overloaded all-star cast of talent such as Jeff Bridges, John Goodman, Penélope Cruz, Luke Wilson, Jessica Lange, Mickey Rourke, Giovani Ribisi and Val Kilmer, the film is not just like bringing one of Bob Dylan songs to life, but like bringing the whole of his 2001 masterpiece “Love and Theft” to the silver screen.
Packed with carnival Americana to the point of overflowing with what Greil Marcus would call “that old, weird America”, the movie is a trip through time – forwards or backwards, who knows – to a dystopian landscape of North America where confusion is king and a despotic government has led to a world of anarchy, civil war, totalitarianism and the struggle for freedom. It’s a film about treachery, double-crossing, backstabbing, taking things too far and, ultimately, redemption. Among all this chaos are some of the greatest live performances of Dylan’s music ever captured on tape, as he and his band run through songs like the Confederate anthem ‘Dixie’ or his own ‘Cold Irons Bound’, ‘I’ll Remember You’ and ‘Drifter’s Escape’.
You wouldn’t know it from this description, but the film is also deeply funny. Combining his own famous wit with that of Seinfeld producer Larry Charles, Dylan had originally pitched the idea that they work together on a Jerry Lewis inspired slapstick sitcom for HBO, but the story goes that as soon as they won the interest of the studio, he lost interest in the project. Dylan and Charles turned their attention to the big screen, then, and wrote what went on to become Masked and Anonymous.
Much like Renaldo and Clara before it, Masked and Anonymous was originally slated to be a three–and–a–half–hour epic. Together, the pair wrote a mammoth 155-page screenplay for the picture, and Dylan insisted, against the wishes of the film’s producers, that Charles shoot the script in its entirety.

The script for the movie might just be the perfect distillation of Dylan’s body of work, too, so it’s no wonder that he wanted to capture every moment of it. It deals in dreams and schemes, double meanings and double crossings; it deals with love and family and with the history of America and the whole human race. It deals with the big and the small and the individual and the collective. It deals with the here and the now and the now and then.
Much in the same way that a lot of his writing about other people’s music in The Philosophy of Modern Song gives a more accurate insight into his own life and work than almost anything in his autobiography Chronicles does, Masked and Anonymous allowed Dylan the room to reveal more of himself than he ever had before, through his own character in the movie, Jack Fate, and through others like John Goodman’s Uncle Sweetheart, who at one point explains: “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 manipulatin’ the forces of evil”.
Elsewhere, Penelope Cruz’s character puts it more succinctly when she says, “I love his songs because they are not precise”.
In the grand climax of the movie, Dylan’s character lays it all out on the line when he says, “I was always a singer and maybe no more than that. 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 and 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”.
16 years down the line, speaking in Rolling Thunder Revue: a Bob Dylan Story by Martin Scorsese, Dylan said: “When somebody’s wearing a mask, he’s gonna tell you the truth. When he’s not wearing a mask, it’s highly unlikely”. While he isn’t wearing a mask in the Scorsese “documentary”, he has his Jack Fate mask on all the way through Masked and Anonymous and was as open and honest with his audience as he ever has been, hardly anonymous at all, even at one point answering the question “you ever let it all hang out?” with the quip “it always has been hanging out”.
The film continues the poetic carnival and exploration of America, freedom and tyranny, which was first explored on the Rolling Thunder Revue and captured in Renaldo and Clara, taking it all the way to the end of the line. Masked and Anonymous succeeds in what it aims to do where the earlier movie maybe did not, though Dylan himself was not so happy with the finished picture, saying in a 2012 interview: “Whatever vision I had for that movie, that never could’ve carried to the screen. When you want to make a film and you’re using outside money, there’s just too many people you have to listen to”.
“I’m glad some people like it. I know people who do,” he explained. “There’s some performances in there. John Goodman. Isn’t he great? And Jessica Lange. Everybody was really good in it. Everybody except me! I had no business being in it, to tell you the truth. What’s her name, Cate Blanchett should’ve played the character that I played! It probably would’ve been a hit movie”.
Never Miss A Tale
The Far Out Bob Dylan Newsletter
All the latest stories about Bob Dylan from the independent voice of culture.
Straight to your inbox.