I think Todd Haynes was trying to be creative and different at the same time, but all it did was confuse me. You can blatantly tell that he was trying to tell Bob Dylan's story in a different way, by way of using four different characters.
He began with Woody, the young boy who had a strong love for folk music. You saw that he carried his guitar everywhere he went, playing and singing for the people he encountered. He would have rather risked his life than give up his guitar, as we see when he jumps off the train into the water. He even went as far as visiting Woody Guthrie in the hospital, someone he didn't even know because he loved what he did so much. I saw that as Haynes trying to show us what Dylan might have been like as a child. The most radical character, Jude, was supposed to represent Dylan in his prime, with his career taking off. He was carefree, partied all the time, ad spoke his mind. In the end, it slowly started crumbling down for him. The last character, Johnny Walker was supposed to be Dylan late into his career. He had finally settled down and gotten married, and had some kids. He quit the singing after a while and gave his life to God, which was an unexpected turn in the film in my opinion. The fourth character was the old man with the dog, which could have represented Dylan after it was all over and he was just living a simple life. After escaping town on a freight train, he rediscovered his love for folk when he found Woody's guitar and began playing it.
As for my opinion of it all, after watching the film, I had to really step back and figure out why Haynes had done what he had done. I commend him on trying to be different, and later on I understood it, but I think he could have done a lot better. It was like watching a documentary/feature film/ period piece all rolled into one, and that was just way too much. I think it would have made a lot more sense if he would have just done it the standard way and had a simple biopic without all the" smoke and mirrors". It would have made a lot more sense instead of taking the audience back and forth.