When I started reading about Dylan, I began with Chronicles, Volume I, Dylan's own reflections, thinking it would be a good insight into that crazy mind of his. I've been a fan of his music for a long time, and I was excited to learn more about his life and creative process. However, I didn't get far in the book before I got too angry too carry on. The truth is: Bob Dylan is kind of an asshole. First, it came off as confidence, which is unusual and sort of admirable in an artist. Then he was egotistical, but sure, ok, who isn't now and then? But as he went on, he just kept talking about how inspired he was, how he "knew those [folk] songs from the inside" and I started to yearn for just a touch of humility or self-doubt to break up the Divine Poet tone that was developing. A few remarks about a woman he knew who was "good to the eye" who would "take up the collection" and whom he would "split the money with... later, but it was too much of a hassle to do it all the time" set me over the edge, and I had to put it down.
The next book I tried was Robert Shelton's aforementioned 1986 biography of Dylan, which idolized Dylan even more than he did himself. I didn't even make it 2 pages in. According to Shelton, the book is: "...A story about a poet and musician who was born and reborn time again, who "died" several "deaths" and yet continued to live. It is the story of a popular hero who denied his own heroism [not from what I've read; see above], of a rebel who so eloquently challenged his culture that he helped build a counterculture, and who then turned against the excesses of what he'd helped create."
Perhaps I just feel compelled to refute these unbelievably overdramatic claims, but I CANNOT, in good conscience, say that Bob Dylan became what he is because he is or was some godlike, visionary talent. To be sure, he is an incredibly talented songwriter, and appeared at just the right time to become the voice of a generation. He's a strange and compelling public figure and probably a genius in many ways.
However, why did he become so huge, and not someone else? No female artist of his generation would have been seen as such a visionary, so committed to her art. No person of color would be as talked about or widely recognized. I'd even go so far as to say that no one without a middle-class upbringing and a cultural and musical education like Dylan's would have had a chance at his success. In addition to his truly unique and abundant talent, Bob Dylan would not be where he was without a significant amount of privilege, but apparently people tend to mistake that for divine intervention.