“At midnight, all the agents and the superhuman crew come out and round up everyone that knows more than they do.”
– Bob Dylan
“All roads led to Bob Dylan,” as musician Martha Wainwright rightly remarked. “He is the artist that all artists are led to.”
Bob Dylan’s influence on modern music is overwhelming. Time and time again, he redefined the boundaries of songwriting, never allowing himself to be straightjacketed by a single identity or style.
While it’s impossible to pick the “greatest” Bob Dylan song, most fans and critics would agree that Desolation Row is one of his crowning poetic achievements, as it blurs the lines between music and literature.
Throughout my years of listening to the song, my enjoyment was mostly in its sensory event. I loved the dark and surrealist lyrics being sounded in nonchalant contrast to its strangely gleeful instrumentals, accompanied by the cinematic imagery that were screened on my mind. However, I had never really gotten to a practical understanding of the song.
Recently, though, I was just casually listening to the song with my third cup of coffee one day, when I suddenly realized, “Oh my God. Maybe this is what it means.”
So, what is Desolation Row possibly about?
As a background, Dylan’s writing of Desolation Row was highly influenced by the Modernist poet T.S. Eliot’s The Waste Land, which portrays the cultural traumas of the post-World-War-I society. Like the poem, the song consists of seemingly disparate vignettes of literary, mythological, biblical and historical characters.
In terms of what or where “Desolation Row” is, it’s hard to say for sure. According to Dylan in a 1965 press conference, it’s a real place in Mexico that’s famous for its Coke factory. But considering Dylan’s reputation for trolling journalists especially during that time period, it’s probably wiser not to take his word for it.
Meanwhile, some scholars have suggested that the name “Desolation Row” is a combination of Jack Kerouac’s Desolation Angels and John Steinbeck’s Cannery Row.
Whatever the truth may be, we do know from the song that it’s not exactly a pretty place.
Right from the iconic first line, “They’re selling postcards of the hanging”, we can discern that Desolation Row is a place of disorder and chaos. The line is likely inspired by a real-life incident in Dylan’s hometown of Duluth, Minnesota, where three black man were lynched, and photographs of the lynching were sold as souvenir postcards.
We then see the characters taking the law into their own hands by “painting their passports brown”, a color reserved for government officials. We also see a subversion of gender roles, in which “the beauty parlor is filled with sailors.” The mental images that emerge from each line of lyrics just get stranger and stranger, the longer we linger in Desolation Row.
From my personal point of view, I think of Desolation Row as being symbolic of “the real world”, so to speak. I think of it not so much as a physical place, but rather a state of mind, of seeing the world as it really is, instead of through the lens of social norms and ideals.
Dylan repeatedly describes Desolation Row as being socially taboo. It is a place that the characters “peek into”, are “punished for going to”, and “escape to”.
Life in Desolation Row is depicted as being counterintuitive, complicated and unpredictable. We witness the characters being in situations that are out of line with what they are generally known for.
Rather than seeing Cinderella passively waiting for romance, we see her doing the flirting. And she is longed after, not by Prince Charming, but by Romeo from Shakespeare’s tragedy Romeo and Juliet.
We see Einstein being disillusioned with the destructive effects of scientific progress, and leaving his illustrious career as a physicist to play the electric violin in Desolation Row.
We see Casanova not as the notorious seducer that he is known to be, but as a helpless victim.
Life outside Desolation Row, on the other hand, is depicted as being filtered and suppressed, in the sense that people are punished for knowing too much. In a line reminiscent of the KGB of the Soviet Union (or governments just about anywhere, really), Dylan sings, “At midnight, all the agents and the superhuman crew come out and round up everyone that knows more than they do.”
This is the point that I believe Dylan is trying to emphasize in the song, that knowing the truth comes at a cost. You may be punished for what you know, or for thinking differently.
Not only that, you may feel a sense of loneliness and alienation from the rest of society for how you view the world — hence the name, Desolation Row.
Like how Carlos Castaneda put it, you may find yourself on a sempiternal “journey to Ixtlan”. No matter what you do, you can never truly find your way back to ignorance after knowing the truth. The only place that you belong to is Desolation Row: a common home for misfits and nonconformists.
Now comes the question, how does Desolation Row relate to our everyday life?
On a personal level, I’d say that the song has opened my mind to seeking a more holistic perspective of the world, that goes beyond society’s black-and-white definitions. There are always grey areas and multiple dimensions to every story, because life is often more complicated than we think.
And with that, albeit at the risk of sounding cynical, I’ve learned to be more neutral and moderate in my views of the world.
To paraphrase a quote by Mark Manson, things are rarely as bad as they seem, and things are rarely as good as they seem either.
For example, when I travel, I’m less likely to idealize other countries as having the greener grass. Because I’m aware that every country has its own problems.
Say, when I’m in Singapore, I may be impressed by its modernity. But I’m also aware that in some ways, the country’s successes are also its challenges. For one thing, its relentless working culture may have turned itself from a third-world nation to first-world. But from a mental-health perspective, it has also made Singaporeans some of the most stressed and burnt-out people in the world.
Life is rarely what it seems, and the poetic genius of Bob Dylan’s Desolation Row is in how it unveils this reality to us, by letting us into the strange and sublime recesses of Dylan’s ever-inspired imagination. Once you walk into Desolation Row, there’s no going back out in the same way.
Bob Dylan illustrates this sentiment best in the final lyrics of the song. He receives a letter from the “outside world”, to which he reacts apathetically. He is bored by the two-dimensional depictions of the people mentioned in the letter, that he had to “rearrange their faces and give them all another name.”
“Right now, I can’t read too good. Don’t send me no more letters, no,” he tells the sender. “Not unless you mail them from Desolation Row.”

