“Boots of Spanish Leather” by Bob Dylan

Bob Dylan cut "Boots of Spanish Leather" alone in New York on August 7, 1963, just his voice and a fingerpicked acoustic guitar, and it came out the next year on The Times They Are a-Changin', with Tom Wilson producing. It's a quiet, aching ballad built as an exchange of letters between two lovers at a crossroads, a man's voice and a woman's trading off, with the open sea looming over it.

Old ballads run underneath it. Dylan scholar Michael Gray points to "Blackjack Davey", another song where footwear of Spanish leather matters, and one Dylan would record himself for Good as I Been to You in 1992. More often it gets compared to "Scarborough Fair", in both melody and words, the same well Dylan drew on for "Girl from the North Country".

Written with AI assistance from RockLists chart data, MusicBrainz and Wikipedia.