For me, Dylan's singing worked well in the early days when he sounded like a classic folk singer of the Woody Guthrie kind. I also think this was his most artistically successful period. More than any single figure, he was responsible as I see it for ensuring that Rock music could be art, and high art at that. For me though, his voice was less successful during the Rock star years of 1965-'66. It could also be argued that his songwriting had started to tail away by '66, but others would violently disagree about this given that the rambling "Blonde on Blonde"(1966) is widely seen as his masterpiece. He changed his voice for the "Country" phase of "Nashville Skyline" (1969), and it worked well for him. "Blood on the Tracks" (1975) was a real return to songwriting form, and I don't think he's come close to those musical and poetic heights since.
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