@mahgister
Before I say anything, you must afford me the right to my opinion. I am a person with perhaps more complicated opinions than others. Bob Dylan is about six years older than I am, but we're basically of the same generation even though I am considered a Baby Boomer and he of the Silent Generation. He wasn't at all silent, I think we can all agree on that.
When I am afforded extra, kind of "inside" information about celebrities, I often make judgements. I live in L.A. and I often receive this kind of information. From what I have heard, Dylan is a sad person. Although he has been with quite a few women (as have I) and fathered children (not I), he seems to be pretty much alone. He has never developed familial ties.
The roots of Dylan's early relations with women are well defined in the recent film about him, "A Complete Unknown." The film pretty much ends with one of the women he was with (Joan Baez?) flipping him off. The film portrays him as a person who is more interested in himself than anyone else. I think his later years have shown him to be a kind of recluse.
How has all of this affected his music? His music about social matters are strong and don't seem to be affected. His music about personal matters, however, do seem to be affected by this. Just listen to how he writes about women. Kind of Madonna/whore syndrome. Does this make him less of a good poet. Yes. I say yes.
Leonard Cohen also had complicated relationships with women, but his songs are so nuanced on the matter. Leonard Cohen writes about relationships in so much more of a loving way than Dylan. He sees himself as an actor, whereas Dylan pretty much sees himself as a victim. I'm sorry. I'm a poet and I listen to lyrics.
In regards to his stance on social matters, I think Dylan was important. But so were other singers who influenced him. Woody Guthrie and Pete Seager. Probably Hank Williams. So to summarize, as a social commenter, Dylan was important and strong, although there was a lineage behind him. As a writer of personal matters, Dylan was pretty weak, especially compared to songwriters around him like Leonard Cohen and Joni Mitchell, who were able to see themselves in their writing.
Bob Dylan's poetics was often pretty lazy. He'd throw in an extra word not used in conversaton to complete an iamb. (Unstressed, stressed.) It was not really noticed. People didn't care about it because his social songs were so new and strong. Although he has a witchy woman in "Tom Thumb Blues," he also has strong and beautiful imagery. In "Maggie's Farm" he is the victim of a woman. On one of my favorite albums (I have almost all of his work on vinyl) "Nashville Skyline," women are idealized. But the music is lovely and there is always Johnny Cash.
I understand that probably a lot of writers and poets who have been awarded the Nobel have lived lonely, screwed-up lives, but I don't know about them, and I do know something about Bob Dylan.
On the other hand, Leonard Cohen lived a somewhat magical life. He spent years in a Buddhist monestary trying to figure himself out as he got older. People loved him and he loved others, even those he had to leave.
Joni Mitchell was probably more self-aware in her songs than anyone. I listen to the lyrics. In the future I will post songs that I think are well wrought, with strong lyrics. I admit that "Tom Thumb Blues" is one of those songs. The lyrics stand up and are complex. But so many of Bob Dylan's songs don't stand up so well. And in very few, if any, is he self-aware.
So, I am not a friend or confidant of Bob Dylan and I may be totally wrong in my judgement. Some people might say I'm wrong to judge at all. Yet, I do. And that's me.