Al Kooper, who played organ and piano on the album, claimed in his autobiography that Desolation Row was Eighth Avenue in New York City. At the time, this was a very dangerous part of town. Cannery Row, by John Steinbeck, is also a possible source for the song, as is The Waste Land by T.S. Eliot (who is referenced in the song).
The song describes a town of some sort, full of lowlifes and losers. The various characters receive only a line or two each, yet Dylan still manages to be evocative and bring forth images of crazy, nonsensical townspeople. Desolation Row would seem to lie on Highway 61, perhaps at the end of the line in Dylan's native Duluth, Minnesota, where the horde of freaks congregate after being rejected from elsewhere. Dylan's feelings about this place seem contrary; it is clearly a town full of mean, stupid and insane people, yet he seems nearly jubilant about being there. On the other hand, it is also a land of counter-cultural rebellion. At the time, political dissidents such as socialists and pacifists were shunned; these rejects are the inhabitants of Desolation Row, described in the song. Indeed, most of the characters mentioned were rejected from their society for being some sort of freak, from the Phantom of the Opera and The Hunchback of Notre Dame, shunned because of their appearance to Cinderella, who forces her way out of her assigned role in society through sheer will power.
The Threepenny Review describes the song thusly:
"(I)n 'Desolation Row' the listener's eye is directed toward a circus of grotesques: a beauty parlor filled with sailors, a commissioner masturbating as he caresses a tightrope walker, a whole city in disguise. But whoever they are, nearly all of the characters in the song share one attribute: they're not free. They are prisoners of judges, doctors, torturers, an entire secret police, and the worst part is they may have recruited its troops from their own hearts. If they are not free it is because they are prisoners of their own ignorance, their own vanity, their own compromises, their own cowardice. By the way they are sung, the saddest lines in the song echo with all that one man used to be, could have been, will never be again: "You would not think, to look at him, but he was famous, lonnnnnnng ago," the word long stretched out just as long as it will go, all the way back to the time when the Einstein the man was then wouldn't even recognize the Einstein he is now."
Dylan seems to believe that if the people of Desolation Row continue to grow, the world will become entirely the same, full of sad, lonely losers. This is Dylan's pessimistic vision of the future; where everyone, even Bette Davis, Cinderella, Casanova, and Albert Einstein, is tragic and pained, living in a scrap of a town.
The lyrics to "Desolation Row" are delivered in a laconic tone and sound like a description of a surrealist or symbolist painting or a film by Federico Fellini. The place described is having abnormal morality, where they sell "postcards of the hanging", and the social status quo is not followed: "beauty parlor (is) filled with sailors" and the "blind commissioner", who has "one hand tied to the tight-rope walker" while he masturbates with "the other (hand) in his pants". All these strange characters "need somewhere to go" and the place turns out to be Desolation Row.
The second verse concerns Cinderella and Romeo, who has apparently come to woo Cinderella; she "seems so easy". He is rebuffed, however, as someone says "you're in the wrong place, my friend/You better leave." After this disagreement between "someone" and "Romeo," Cinderella is left "sweeping up/on Desolation Row" after the ambulances leave. Most reviewers agree that Romeo and Cinderella are in Desolation Row because they do not fit into their assigned roles. Cinderella is supposed to fall in love with a prince, and Romeo is meant to love Juliet--their refusal to heed these roles and rules sends them in exile to Desolation Row.
The next verse mentions Cain, Abel, the Hunchback of Notre Dame and the Good Samaritan as being inhabitants of Desolation Row. At night, the sky is becoming cloudy and threatening a storm ("the moon is almost hidden/the stars are beginning to hide") and everybody, except for Cain, Abel and the Hunchback, have gone inside (even the "fortunetelling lady"). Those who are not making love are "expecting rain" (note: "Everybody is making love/Or else expecting rain" is a popular, oft-quoted line from this song), all except for the Good Samaritan, who is obliviously getting ready for a show at a carnival. That he is a carnie is perhaps notable, implying that possessing the quality of goodness (as the Good Samaritan does) makes one a carnival freak; he is, like the other inhabitants of Desolation Row, dissimilar from his neighbors because he is neither making love, nor expecting rain.
The fourth verse is about "Ophelia" (see Hamlet), who does not live on Desolation Row, though she does spend "her time peeking" into it. She does not live there because she has bought into the dominant status quo. As a result of conforming, Ophelia is already an "old maid" "on her twenty-first birthday." Her life is meaningless, as she spends all day trudging through a boring, irrelevant life which she takes seriously to the detriment of her real emotional and mental existence--"her profession's her religion/her sin is her lifelessness." Thus, her boring acceptance of mediocrity and banality is what keeps her from moving to Desolation Row. It is worth noting that Ophelia, in William Shakespeare's Hamlet, commits suicide.
The next verse describes a washed-up Albert Einstein (who is "disguised as Robin Hood"). Einstein was not always taken seriously in his time, and he was a noted iconoclast, so his presence on Desolation Row is not surprising. He is not an illustrious physicist, though, but a bum who sniffs drainpipes and bums cigarettes off strangers. Things used to be different for Einstein, though, as he used to be famous "for playing the electric violin/on Desolation Row".
Though much of the song is difficult to quantify to any real-word referent, many reviewers claim the tenth verse has a definite intepretation. To some, this verse refers to the actions of the federal government of the United States. Specifically, programs such as COINTELPRO, run by the FBI to discredit, sabotage and perhaps assassinate counter-cultural leaders. "... all the agents/and the superhuman crew" (i.e. FBI and law enforcement agents, enforcers of the status quo) "round up everyone/that knows more than they do" (isolate all freaks and people who don't fit into mainstream society). These iconoclasts are then brought to "the factory/where the heart-attack machine/is strapped across their shoulders" (perhaps referring to mind-and-heart-numbing suburban existence, represented by the "heart-attack", being tied to former idealists by the crushing banality of modern life). Finally, "insurance men" go to "check to see that nobody is escaping/to Desolation Row," lending credence to the idea that Desolation Row refers to a place where society's freaks and rejects can escape to and find solace in.
Cultural references in the song: Bette Davis, Cinderella, Romeo and Juliet, Cain and Abel, The Hunchback of Notre Dame, Good Samaritan, Ophelia, Albert Einstein, Robin Hood, The Phantom of the Opera, Casanova, Noah, Nero, Neptune, Ezra Pound, T.S. Eliot, Titanic, calypso music