Bob Dylan’s Favorite Song Might Surprise You

The question of which song a songwriter cherishes most—often differing from public favorites—offers a unique window into their artistic mindset. When the artist is as enigmatic as Bob Dylan, the answer becomes particularly intriguing.

Bob Dylan Cited This Eleven-Minute Track As One of His Best

Bob Dylan, the iconic folk-rock artist, is known for his lengthy compositions. In 2020, he released “Murder Most Foul,” a nearly seventeen-minute track exploring the JFK assassination. His 1997 album Time Out of Mind featured “Highlands,” clocking in at sixteen minutes and thirty seconds. Even earlier, in 1966, Dylan experimented with extended lengths with “Sad-Eyed Lady Of The Lowlands” from Blonde on Blonde, lasting 11 minutes and 23 seconds.

Dylan once told Robert Shelton that “Sad-Eyed Lady Of The Lowlands” was the “best song [he] ever wrote,” according to No Direction Home: The Life and Music of Bob Dylan. He described it to Jules Siegel as “religious carnival music,” as detailed in Clinton Heylin’s Dylan: Behind the Shades. Dylan admired the production, despite the song containing overt references to his then-wife, Sara.

“Sad-Eyed Lady Of The Lowlands” Challenged the Band

Kenny Buttrey, the drummer on “Sad-Eyed Lady Of The Lowlands,” recalled Dylan’s vague instructions before recording. Dylan indicated he would intersperse harmonica solos between verses and improvise. This lack of direction is noticeable in the final recording.

“We were preparing ourselves dynamically for a basic two-to-three-minute record,” Buttrey explained in Dylan: Behind the Shades. “If you notice that record, that thing after, like, the second chorus starts building and building like crazy, and everybody’s just peaking it up ‘cause we thought, ‘Man, this is it. This is gonna be the last chorus, and we’ve gotta place everything into it we can.’ And he played another harmonica solo and went back down to another verse and the dynamics had to drop back down to a verse kind of feel. After about five, six minutes of this stuff, we start looking at the clock, everyone starts looking at each other. We’d built to the peak of our limit, and bang, [there] goes another harmonica solo.”

“After about ten minutes of this thing, we’re cracking up at each other, at what we were doing,” Buttrey continued. “I mean, we peaked five minutes ago. Where do we go from here?”

Dylan’s control over the band’s anticipation likely contributed to his appreciation for “Sad-Eyed Lady Of The Lowlands.”