Books Analyzing Dylan's Music
Highest Recommendation
Song and Dance Man by Michael Gray.
A good book covering much of Dylan's career. Looks at Dylan's work mostly in terms of the lyrics. Especially good at discussing parallels between Dylan's lyrics and traditional folk song and blues lyrics.
Also Recommended
Performing Artist: The Music of Bob Dylan Volume One, 1960-1973 by Paul Williams
This book focuses (as should be obvious) on Dylan the performer. Williams is more a fan than a traditional critic, but his book does what it sets out to do - send the reader back to the primary material with enthusiam.
Performing Artist: The Middle Years, 1974-1986 by Paul Williams
A continuation of the first volume. Since Dylan's work was a bit weaker in this period, the book suffers somewhat in comparison with the first volume. Particularly puzzling is Williams' defense of the horrible movie "Renaldo and Clara" as a masterpiece. Still largely an enjoyable read and it does point out some of the higher points in Dylan's music during his weak period.