1966 Classic Hit, Which Bob Dylan Never Performed, Is Ranked His No. 1 Best Song
Bob Dylan's musical catalogue has an enormity that I still haven't fully made my way through yet.
To grasp the enormity of everything Dylan has released over the years, you have to listen to 40 studio albums, 21 live albums, and all of the massive bootlegs releases, which include outtakes, alternates, and more live performances. That's to say nothing of his collaborations with other artists.
The point is that it's hard to definitively go in and rank his best tracks. Everyone has a different opinion. If I were to go ahead and rank my favorites, I think it would take me an incredibly long time. Pastedecided to take on the challenge, and I think their top spot went to one of Dylan's best.
'Sad-Eyed Lady of the Lowlands'
The top spot on the "62 of Dylan's Greatest Songs" list went to the closer from Dylan's legendary 1966 release "Blonde on Blonde," "Sad-Eyed Lady of the Lowlands."
Normally, I would include a live performance of the song to give you a feel for what it's like, but as you can see, there's only audio on the clip above. That's because Dylan has never performed this song live, and once you understand the story, that will both get more understandable -- and more confusing.
Dylan was at the end of some of the most revolutionary musical output ever when he released "Blonde on Blonde." He was on a level of stardom similar to The Beatles with the added pressure that he was seen by many as a "prophet." He'd been consistently touring and performing for pretty much his entire career, and the public spotlight was beginning to weigh on him. In fact, "Blonde on Blonde" was recorded in the middle of a tour.
Because of all these factors, you can hear a noticeable wear on Dylan's voice throughout the album. His often mocked nasally rasp was at its most noticeable throughout all of "Blonde on Blonde," and combined with his intense songwriting, he created an album that attacks you with its emotions, words, and images. It's really a sign of the times for both Dylan and the era.
You could really pick any song from "Blonde on Blonde" and put it as his best. It's easily one of his greatest accomplishments as a musician, but "Sad-Eyed Lady of the Lowlands" really stands out. The song clocks in at a whopping 11 minutes and 16 seconds, and is largely believed to be about his wife, Sara Lownds.
The two secretly married in 1965 at the height of Dylan's apotheosis. It was clearly a passionate moment for him, as for the entirety of "Sad-Eyed Lady of the Lowlands," Dylan waxes in his style about her, their relationship, and the reverence he has for her. He sings of her "saintlike face" and "ghostlike soul," and her eyes "where the moonlight swims." It's a deeply beautiful song that sees Dylan at his most romantic.
The relationship wouldn't last, however. The pair divorced in 1977 after a lengthy breakup, which became the subject of Dylan's 1975 album "Blood on the Tracks." Among this and the following album, "Desire" are many tracks discussing the pain and the love lost of his marriage, including the very un-subtle "Sara."
The reason I mention this is to highlight the mystery of "Sad-Eyed Lady of the Lowlands." Dylan has performed many songs from Blood on the Tracks live, and has performed "Sara" many times. All of these songs are much more explicit about their relationship to his marriage, and yet, "Sad-Eyed Lady of the Lowlands" has never seen a live stage.
Ultimately, with Dylan, we'll never know. It's still a fascinating element to one of his most legendary tracks, that while it isn't my top favorite, it's absolutely deserving of a top spot on a list like this.
Related: 1965's Most Controversial Song Ranked in 'Top 10 Rock Songs Ever' Created a Music Legend
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This story was originally published May 20, 2026 at 8:35 PM.