It’s hard to pick a favorite among the volumes of the Bootleg Series, but I might cast a vote for Volume 8, Telltale Signs, a collection of rare and unreleased material recorded between 1989 and 2006.
During that span, Dylan released Oh Mercy and Under the Red Sky, followed by his folk music cover albums and then the celebrated trilogy of Time Out of Mind, Love and Theft and Modern Times.
He was at a creative peak, especially from the late 90s on, and Telltale Signs makes it clear that, as usual, many special songs never made it onto those albums. Among those is ‘Red River Shore’ (covered on the blog in early 2009) that maybe ties ‘Blind Willie McTell‘ as the best song ever left off of a Dylan album.
Meet Me In Montauk 