27. "Sad-Eyed Lady of the Lowlands" (1966)
In his 1976 classic "Sara," Dylan explained this song as a tribute to his first wife, whom he had secretly married just months before starting work on Blonde on Blonde. "Staying up for days in the Chelsea Hotel," he sang wistfully, "writing 'Sad-Eyed Lady of the Lowlands' for you." Like so many stories about Dylan's past, the anecdote from "Sara" is both fascinating and mostly false. "Sad-Eyed Lady of the Lowlands" is indeed an ode to Sara Dylan, but he largely wrote it on the spot during the dead of night in a Nashville studio. While the session musicians he'd hired played cards, he sat down and wrote the sweetly surreal verses. "It started out as just a little thing," Dylan said in 1969. "But I got carried away somewhere along the line."
After eight hours of work, Dylan called the band members into the studio at 4 a.m. and gave them minimal instructions. They had no idea the song would keep going for 11 minutes – and they were stunned once more when, afterward, Dylan told them they had nailed it on the very first take.