to me there are two diff angles to look at this question from... how did dylan become popular initially and how did he become so hugely popular later?... blowin in the wind was truly an anthem for the antiwar contingent, for lack of a better word, as was the times they are a changin' an anthem for the generation gap as well as for the discontent the younger generation felt toward those in power in general... and of course songs like don't think twice just added fuel to his popularity in describing the angst of men-women relationships... peter paul and mary contributed to his initial popularity in recording these songs
but i think it was his acute sense of social injustice that made his songs so popular "it takes an ugly voice (and an ugly singer?) to be understood" ---one of my fav quotes of his later in his career, as he turned electric and kind of chameleon-like in chasing diff styles of music, i think he still had some of that originality, but alienated many people looking to him to continue producing anthems of such daring, brilliant metaphor as blowin in the wind... yet his desire to produce new music and to not look back has many parallels, even some to our lady of siquomb one song i think is absolutely bril in the story telling fashion he made so popular was/is percy's song, about a man sentenced to 99 years for killing four people driving drunk... the portrait he paints of the judge is really quite illuminating..."turn, turn, turn, to the crying of the wind" as the hook, if i remember right, shows again his subtle yet powerful use of metaphor what can you say? the man was a poet alan
