As someone who discovered electric Dylan first, I always found it hard to engage with the earlier material; there seems something missing not just in the music, but in the words. It was only when listening to the Bootleg Dylan album that I began to understand why. Everyone always said that the quintessential 'protest' period anthem was 'Blowin' in the Wind'; the Bootleg Dylan includes his performance of a Civil War-era spiritual, 'No More Auction Block', from which Dylan has admitted lifting the tune for "Blowin'…" I now think he lifted more.
Considering its iconic status in peace movements and folk music even today, and considering it was written by the most articulate poet of a generation, "Blowin' in the wind" is actually full of awkward phrases.
"How many roads must a man walk down,
Before you call him a man?"
This is the first line of the most important song of a generation… yet look at it. The man/man repetition is technically maladroit, creating an unwanted internal rhyme. But worse than that, it is actually using the same short word in two different senses in the course of the same line: "a man" first is "someone" or perhaps "anyone" or "me", while seven words later "a man" is used as "a grown person" or "someone whose opinion should be listened to". The answer presumably is some but not many.
"How many miles must the white dove sail
Before she sleeps in the sand?"
The answer here, to "how long before the dove can sleep having delivered its message of hope" is presumably too many.
"Yes, and how many times must the cannonballs fly
Before they are forever banned?"
This line is perhaps the point at which you can start to unravel the song. The song was written in 1962, 6 years after the first Hydrogen bomb was detonated, just before Vietnam brought modern technology to the battlefield. The answer to the question is none: cannonballs no longer fly, and in fact haven't since the supremacy of rifled artillery was established in the American Civil War in the 1860s. As an image of 20th century warfare, it is not just weak but wrong. This is a sentiment that belongs to the 19th century.
So does the second half of the line. Banning is what headteachers do: earrings, bleached hair, fluorescent socks. The more honest modern peace protestors say "Not in My Name". The Western students of the 1960s, rather than saying "ban the bomb", might with more justice have said "renounce the bomb": telling their (democratic) government that they did not wish it to use the threat of nuclear war as an instrument of foreign policy, while willing to admit that other governments did not face similar pressures and wouldn't have listened if they did.
"The answer, my friend
Is blowing in the wind
The answer is blowing in the wind"
The sense of the song must be not that the wind has the answer, but that there is no answer; this is how things are and how they will stay.
How can it be that this message has been adopted as one of hope, even triumph? It could be that people aren't listening to the words, in the same way that the American Right adopted Springsteen's "Born in the USA" as an anthem, assuming it reflected their simplistic patriotism, rather than questioning it. But I think the truth is that what has sold this song as an optimistic one is Dylan's delivery of it, which makes it sound as if the answer is "not yet, but soon".
So we have a curious mixture of archaism in technology and a belief that banning (or not banning) is in someone's power as a possible outcome. To return to the 1860s, and "No More Auction Block":
"No more auction block
No more, no more,
No more auction block
Many thousands gone
No more driver's 'lash for me
No more, no more
No more driver's whiplash for me
Many thousands gone"
The song is one of mournful triumph, an expression of release, of gratitude for the liberation of the slaves delivered in 1865 after the Civil War, regretting the terrible cost in pain and sorrow through all the years of trial, but looking forward in sombre optimism. Or to put it another way "How many times on the auction block?" "Too many , but no more".
Dylan's delivery of this song is clearly the blueprint for "Blowing"; he sounds dignified: wearied, but thankful. Thus undercutting the message of the words as "Who knows when anything will change" is the feeling, more properly belong to "Auction Block", of "Something will change".
"How many times must a man look up
Before he can see the sky?
How many ears must one man have
Before he can hear people cry?
I think that 'seeing the sky' here is noticing what would have been obvious to any normal observer (i.e. slavery being wrong). The second line, if you can avoid the bathetic image of people needing more ears, rather than better ears, makes the same point: how can you ignore all the suffering?
"How many years can some people exist
Before they're allowed to be free?"
This is another 'banning' line; it's actually paradoxical (in modern terms): you can't allow people to be free; they either are free, or they're not. There was, of course, a major historical action which really did allow people to be free… in 1865.
My doubts about the song were based on a vague feeling that somehow the rhetoric was misplaced and ineffective; at face value, in 1962, it is at best a bit of wishful thinking on behalf of a generation deprived of political influence. By noticing how much of this perceived lack of impact derives from the parallels with a song one hundred years older, most of these doubts are washed away. And you can see that Dylan, looking around for examples of good overcoming evil after a long period of darkness and sorrow, might latch onto the emancipation of the slaves as one with deep resonances. He probably didn't have time to notice that the moral was equivocal: after all, there was a war fought at least partly to resolve the issue: was that a good thing or not?