The question of an artist’s favorite work often diverges sharply from public perception. What resonates deeply with the creator isn’t always what climbs the charts or defines their legacy in the eyes of fans. This represents particularly intriguing when considering artists as enigmatic as Bob Dylan, whose creative process and personal motivations remain largely obscured. It turns out, Dylan’s own pick for his best song isn’t a radio staple, but a sprawling, eleven-minute folk epic.
Dylan has repeatedly cited “Sad-Eyed Lady Of The Lowlands” as the song he considers his finest achievement. The track, the closing number on his 1966 album Blonde on Blonde, is a far cry from the concise, three-minute pop songs that dominated the airwaves at the time. Its length and lyrical complexity initially confounded his own band, a testament to Dylan’s willingness to push boundaries and prioritize artistic vision over commercial appeal.
A Lengthy Exploration of Sound and Sentiment
Dylan’s penchant for extended compositions isn’t a recent development. In 2020, he released “Murder Most Foul,” a nearly seventeen-minute exploration of the JFK assassination. His 1997 track “Highlands,” from the album Time Out of Mind, clocked in at sixteen minutes and thirty seconds. Even decades earlier, he was experimenting with longer forms, demonstrating a consistent disregard for conventional song structures. “Sad-Eyed Lady Of The Lowlands,” at 11:23, was a significant departure for its time and remains a standout in his extensive catalog.
According to Robert Shelton, Dylan described “Sad-Eyed Lady” as “religious music.” He further elaborated to Jules Siegel, calling it “religious carnival music,” and expressing pride in achieving that particular sonic blend. The song’s personal nature, containing overt references to his then-wife Sara, likely contributed to its significance for Dylan, despite its unconventional form.
Navigating the Murky Waters of a Marathon Recording Session
However, the song’s ambitious length didn’t necessarily translate to a smooth recording process. Drummer Kenny Buttrey recalled a somewhat chaotic studio session, where Dylan offered minimal direction. The band was initially led to believe they were building towards a final chorus, only for Dylan to launch into another harmonica solo and return to a verse. This cycle repeated itself, leaving the musicians unsure of where the song was headed.
“We were preparing ourselves dynamically for a basic two-to-three-minute record,” Buttrey explained. As the song stretched beyond the five-minute mark, the band began to anticipate a resolution that never came. “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?”
The experience highlights Dylan’s unique approach to recording, often prioritizing improvisation and a sense of unfolding discovery over meticulous planning. While the band may have struggled to navigate the song’s unpredictable structure, Dylan clearly found value in the dynamic tension and the feeling of sustained momentum. The palpable sense of anticipation, and Dylan’s control over those shifting emotions, likely contributed to his enduring admiration for “Sad-Eyed Lady Of The Lowlands.”
Dylan’s choice of “Sad-Eyed Lady Of The Lowlands” as his personal best underscores a crucial point about artistic evaluation. What resonates with an artist isn’t always about commercial success or critical acclaim. It’s about the emotional resonance, the creative challenges overcome, and the personal significance embedded within the work. In Dylan’s case, it’s a sprawling, eleven-minute journey into the depths of his own artistic vision – a vision that continues to captivate and confound listeners decades later.
