I recall being at Crewwe and Alsager, a very liberal college, back in the early eighties. I was doing a Creative Arts Degree and considering writing my dissertation on Bob Dylan. When I realised just how much I was going to have to do to write anything which made sense about Dylan, I backed out pretty quickly. I stuck with the (relatively) unsophisticated work of Woody Guthrie. I didn't write anything profound or original, but I was able to comprehend the man's achievements and at least give some realistic assessment of his importance.
To his detractors, the breadth and depth of Dylan's work are pretensions. Essentially, he gives them far more in a song than they ask for. I think that's why some people like him so little and others rate him as brilliant. I fall into the latter category.
Dylan effectively pioneered a new kind of song. He gave us the complex psychological profile - the most detailed character sketches ever to be attempted in songs. Blowing in the Wind and Chimes of Freedom are great symbolic songs, but they don't have the revolutionary complexity and ambition of Ballad of a Thin Man or It's Alright Ma I'm Only Bleeding. Who else would have tried to show what the world looks like from the point of view of a moralist who is going mad? For all their perception and irony, you don't get that from Lorenz Hart or Cole Porter.
Dylan takes the subject matter of serious playwrights and novelists and presents it in accessible songs. For me that is genius and his honorary doctorate is well merited.