One particular song (among others) that's caught my eye is "Blowing in the Wind". It is a very ironic, rebuking and preaching song that uses a pure and simple English. Dylan himself doesn't do it much justice (as he doesn't most of his songs), so I've also got "Peter Paul and Mary" singing it. In regards to what "the answer is blowing in the wind" is supposed to mean, Dylan once confided in an interview when he was 21 (most likely under the heavy influence of narcotics) that it basically means that the answers to those questions should be self-evident and don't require philosophical insights. The song itself ultimately became so popular that it was sung in the Vatican square. Pope John Paul II was forced to accept it, and even interpreted Dylan's words as meaning that the answer is in fact "in the wind", i.e. in the wind/spirit of G-d (the current Pope Benedict XVI also happened to be in attendance and later admitted that he didn't like the idea of Jews playing rock music on the Vatican grounds).
I myself always wondered why people liked his music so much, since to me it just seemed like the monotonous ramblings of a nerdy Jewish kid. Though the truth is that nobody ever contended that Dylan was a great singer, rather that his greatness lie in song-writing and poetry. His early songs especially convey great truths and political activism through the use of poetry; very far from what rock was back then (which were just simple songs about love). The more I looked into it the more I understood the meaning and even beauty in early Dylan lyrics.
Yet I always stress that we should not, like the American, worship the entertainer, the singer, the joker and the athlete, but rather more noble, less well-known heroes. A century ago entertainers had a much more reasonable, lower place in society. But what of song-writers with meaningful music? Surely it can't be said that they're the same as barber-shop singers? The songs of the political activists in the 60's were the fuel for social revolution in those trying times for America. It is for this reason, I think, that singers have adopted the title of "artists", for their music has gone up a level to become their art (as opposed to Classical music and the like, which has always been a form of art). This is true for the folk-singers of the 60's more than any others in that century. Yet today, singers still use that title, even though there is no more meaning in their songs. How can the likes of "Fidy-Cent" and "Solja-Boy" call themselves "artists"? That, I feel, is a term which has become outdated for singers. Today's singers are, as they were a century ago, just singers.
*Title: Dylans' Hebrew name.