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Once upon a time you dressed so fine
You threw the bums a dime in your prime, didn't you?
At its beginning, the song could be about a woman, a man, or a whole country.
Dylan opens the song with a punch straight to the gut, a taunting rhetorical question ending in "didn't you?" It sets us up immediately to know that we are talking about someone—or something—whose whole identity is up for debate.
Rolling Stone co-founder and publisher Jann Wenner discussed the famous opener, saying, "I don't see it as being about a rich person who falls apart, I see it as being about a comfortable individual, or a comfortable society, suddenly discovering what's going on. Vietnam—the society we're talking about, and you realize, as you become aware, drug aware, socially aware, the disasters of commercial society." (Source)
The disasters of commercial society? (This is only the beginning of the exaggerated, deep, endless readings of pretty much every line of this song.) It might sound far-fetched, but in the mid-1960s, with so much that had been culturally and politically acceptable only a few years earlier suddenly up in the air, Wenner's theory makes perfect sense. America used to just "throw the bums a dime"—and it's suddenly clear that this token action isn't enough.
America is in the midst of a fall from grace. From the first line, the song is both about the loss of personal innocence and about the struggle for civil rights. Or is it?
You've gone to the finest school all right, Miss Lonely
Bob Dylan's caustic critiques and competitive demeanor were sometimes aimed at specific individuals. Naturally, many have wondered who "Miss Lonely" might be.
"The Diplomat," "Miss Lonely" and the "Mystery Tramp" have all been sought in the real world by fans and critics. Among the possible contenders for the origin of "Miss Lonely," people have proposed Edie Sedgwick, a young protégée of Andy Warhol who hung around Dylan a lot in 1965. Her profile as a professional bohemian fits the bill for this sort of mockery, but Dylan claims never to have known her very well.
Sedgwick was nonetheless quite hurt when, in 1966, Dylan married Sara Lownds, an ex-model who had recently divorced her fashion photographer husband (contender for the role of "The Diplomat.") On the other hand, many thought the song was mainly about Joan Baez, and Baez herself believed the song to be about Dylan's then-sidekick, Bob Neuwirth. (Source) No one wants to be "Miss Lonely," whose main role is that of a hypocrite.
For his own part, Dylan insists that his songs are about everyone and no one—and, as a result, they end up being mostly about himself. "I discovered that when I used words like 'he' and 'it' and 'they' and talking about other people, I was really talking about nobody but me," he wrote in his memoir. (Source)
He also offers an alternate, more loopy take on who's who in Dylan songs, saying, "Sometimes the 'you' in my songs is me talking to me. Other times I can be talking to somebody else. If I'm talking to me in a song, I'm not going to drop everything and say, alright, now I'm talking to you. It's up to you to figure out who's who." (Source)
You said you'd never compromise
With the mystery tramp, but now you realize
He's not selling any alibis
As you stare into the vacuum of his eyes
And say, do you want to make a deal?
Jann Wenner, co-founder and publisher of Rolling Stone, says he always thought of this song as his own story—and the story of lots of other kids who came of age in the 1960s.
Jann Wenner explains:
I used to go to the finest schools. Nobody ever taught you how to live out on the street. So, to me, coming from private schools, and my background, being a preppy, ending up at Berkeley, and all of a sudden, taking drugs, things change, you're no longer in a private school, all of a sudden you're running around with Ken Kesey, Hell's Angels, and drug dealers—and one of them's the Mystery Tramp. At some Acid Test, and some weirdo comes up to you, with a beard, a top hat—you stare into the vacuum of his eyes, and ask him, do you want to make a deal. That happened to me. Too many times. (Source)
You used to be so amused
At Napoleon in rags and the language that he used
What is a "Napoleon in rags"? Have you ever encountered one?
This compelling image could be a has-been dictator walking the streets in rags, or it could be a bum on the street who believes he's a dictator. In any case, the idea of "Napoleon in rags" is post-apocalyptic, post-revolutionary, and even a bit postmodern.
"Napoleon in rags" seems like a person who has nothing, but continues to talk as though he knows everything. His world has been destroyed, and he lives in a fantasy of himself. The "you" in the song once looked pityingly at people like this, who took themselves too seriously. Now, the lines suggest, "you" are in the same position. You take yourself too seriously. "Who's laughing now?" Dylan seems to taunt.
The more we think about it, the harder it is not to be a Napoleon in rags—we all take ourselves a little too seriously at times. And as this line points out, it's easy to laugh at someone else in that position, but harder to actually admit that you are a Napoleon in rags yourself.
You're invisible now, you got no secrets to conceal
The song's saddest line is also its most liberating.
Being invisible, lost to the world, at first conjures up the tragic, oppressed invisibility of Ralph Ellison's Invisible Man. It's not cool, Harry Potter's cloak-style invisibility—it's the feeling of having nothing to stand for, nothing to believe in, the feeling of being unseen.
At the same time, in "Like a Rolling Stone," being invisible isn't pure oppression. It means there's nothing left to conceal, no secrets and no past. In Jann Wenner's interpretation, there is nothing more liberating. Wenner explains, "You've got nothing to fear anymore. It's useless to hide any of that s***. You're a free man. That to me is the message. You know: 'Songs of Innocence and Experience.'" (Source)
Just as William Blake had suggested in so many ways through his dark lines, sometimes the greatest loss is the greatest gain, and nothingness opens up the possibility of, well, everythingness. (We know that's not a real word, but we think both William Blake and Bob Dylan would approve, so just go with it.)