We’ve covered Dylan’s Top 12 Albums, so let’s move on to Dylan’s songs. I have to be honest though- the record companies have done a good job of fully cataloging Dylan’s career by releasing countless live albums and collections of all the different versions of even the deep cuts on his albums. So I’m sure there’s plenty I haven’t listened to, and even if I have listened to something, I may not have been able to give it a fair shake. So basically, if I leave something off, it’s not my fault, it’s Dylan’s for creating too much music.

The Top 25 Bob Dylan Songs


25. “It’s Alright, Ma (I’m Only Bleeding)” (1965, Bringing It All Back Home): Dylan was already known for his protest songs, but “It’s Alright, Ma”, recorded in one take, was different, replacing his previous tempered optimism with utter disillusionment.


24. “Just Like a Woman” (1966, Blonde on Blonde): I’ve often struggled with the apparent misogyny of the lyrics (though whether or not Dylan was using sexist overtones to strike back at sexism itself is an arguable explanation), but the creativity of the lyrics and Dylan’s obvious fascination with this one woman pull me in regardless.


23. “Not Dark Yet” (1997, Time out of Mind): On Dylan’s big ‘90s comeback album, “Not Dark Yet” stood out both for its ambient beauty and for its unrelenting optimism.


22. “Maggie’s Farm” (1965, Bringing It All Back Home): There seems to be confusion about whether the uproar over Dylan’s performance of “Maggie’s Farm” at the 1965 Newport Folk Festival was about opposition to his new musical direction toward electric guitars or about poor sound mixing, but the song remains a powerful statement of independence no matter what.


21. “With God on Our Side” (1964, The Times They Are A-Changin’): It starts in a way that may convince you Dylan is showing a patriotic side, but as the lyrics progress this highlight from Dylan’s third album becomes a clear diatribe against the kind of political religiosity that still plays a role in America’s governmental goings-on.


20. “Visions of Johanna” (1966, Blonde on Blonde): This is sort of the go-to song to demonstrate how inscrutable Dylan’s lyrics can be sometimes, and yet as you parse through the bars, “Visions” reveals itself as a lovely meditation on the space between desire and resentment.


19. “A Hard Rain’s A-Gonna Fall” (1963, The Freewheelin’ Bob Dylan): Running 7 minutes long, “Hard Rain” is Dylan’s first protest epic, a desperate screed that eschews any sort of call to action for a simple prophecy of impending doom.


18. “Tears of Rage” (1975, The Basement Tapes): “Tears” originally appeared on The Band’s debut album in 1968, but it didn’t come into its own until this original, collaborative recording was released 7 years later with a more collective anguish.


17. “Simple Twist of Fate” (1975, Blood on the Tracks): On Dylan’s most heartbreaking album, this might be his most heartbreaking song.


16. “Someday Baby” (2008, Tell Tale Signs): “Someday Baby” was a great single on 2006’s Modern Times, but this version on 2008’s Bootleg Series volume is lighter, more hopeful.


15. “Hurricane” (1976, Desire): While lyrically it’s a simple exposé of America’s broken, racist justice system, “Hurricane” is one of Dylan’s most ambitious musical arrangements, using the fiddle to great effect, building on its themes from verse to verse, and ultimately contributing to a swell of support for boxer Ruben Carter’s eventual release from prison.


14. “Girl from the North Country (feat. Johnny Cash)” (1969, Nashville Skyline): Nashville Skyline Dylan is the Dylan with the most interesting vocal performances, and none were better than this plaintive duet with the Man in Black himself.


13. “Knockin’ on Heaven’s Door” (1973, Pat Garrett & Billy the Kid): With a 2:29 run-time, “Knockin’” feels like one of Dylan’s more minor songs, and yet the simple melody of the chorus has had a major impact, and the song has gone on to become one of his most covered.


12. “Shelter from the Storm” (1975, Blood on the Tracks): Dylan is known for his croaky voice, his acerbic wit, and his protest music, but “Shelter” is an example of something he should get more credit for: being able to write a beautiful love song.


11. “Subterranean Homesick Blues” (1965, Bringing It All Back Home): It might be going too far to claim Dylan was the protogenitor of rap, but “Subterranean” finds Dylan right at his sweet spot for using rhythm and rhyme to get across a certain dissatisfaction.


10. “Lay Lady Lay” (1969, Nashville Skyline): Dylan gets his closest to a typical vocal delivery on Nashville Skyline, and “Lay Lady Lay” just may be his most beautiful song. I remember hearing it on The Essential Bob Dylan when I was first discovering his music and thinking it was a completely different artist. Every so often, Dylan succumbs to his romantic side, and “Lay Lady Lay” is the purest version of it.


9. “Sad-Eyed Lady of the Lowlands” (1966, Blonde on Blonde): Speaking of romance, here’s an 11-minute song about Dylan’s then-new wife! Remember that thing I said about “Lay Lady Lay” being the purest version of Dylan’s romantic side? Well, “Sad-Eyed Lady”, which closes the brilliant Blonde on Blonde, is Dylan’s romantic side at its most utterly Dylanesque, from its epic run-time to its absurd imagery.


8. “Mississippi” (2008, Tell Tale Signs): The Bootleg Series collections of the vast troves of Dylan’s unreleased material recorded both live and in-studio, are invaluable and fascinating. But the best is Vol. 8 and its three versions of “Love and Theft”’s “Mississippi”, which is a remarkable song all on its own. But what’s more remarkable is how each version is great in its own way, though I prefer the one that appears first on Tell Tale Signs for the thoughtful way it rolls along to its understated conclusion.


7. “Desolation Row” (1965, Highway 61 Revisited): In the 2010s we know all about the extended length of Dylan’s songs, but when Highway 61 Revisited was released with an 11-minute folk epic at its end, it was new ground for Dylan. While some of Dylan’s longer songs can become tiresome, “Desolation Row” never gets old, perhaps because it was his first. The surreal world Dylan builds over the song’s run-time is as vivid now as the first time I heard it, like a recurring dream .


6. “Mr. Tambourine Man” (1965, Bringing It All Back Home): I made the decision beforehand that Dylan songs with superior cover versions wouldn’t make it on the list, which is why “All Along the Watchtower” (Jimi Hendrix), “It Ain’t Me, Babe” (June Carter and Johnny Cash), and “I Shall Be Released” (The Band) didn’t make the cut. The Byrds recorded a sublime version of “Tambourine”, and I do like it better than Dylan’s, but Dylan’s remains iconic. Where “Desolation Row” would paint a surreal picture of chaos later that year, “Mr. Tambourine Man” painted a surreal picture of peace, and it’s a peace that has never stopped resonating with me.


5. “Don’t Think Twice, It’s All Right” (1963, The Freewheelin’ Bob Dylan): There aren’t too many surprises from here on out- maybe #1, but the next 4 at least are all-timers, the songs a Dylan layperson could pick out of a lineup. “Don’t Think Twice” was the B-side to Dylan’s breakout single, “Blowin’ in the Wind”. On the A-side, listeners got their first taste of Dylan’s protest chops, and on the flip side was one of Dylan’s most personal songs ever, a quiet dismissal of a lover’s selfishness.


4. “Blowin’ in the Wind” (1963, The Freewheelin’ Bob Dylan): I think it’s easy now to dismiss “Blowin’ in the Wind”. As Dylan’s breakout single, it’s been around longer than any of his other songs, and he would go on to write far more complex songs and to craft an entire persona beyond the simple protest folk artist he started as. But the separation between the artist Dylan was and the artist he became actually contribute to the purity of “Blowin’” in retrospect, making it not only one of his best songs but a timeless one.


3. “Like a Rolling Stone” (1965, Highway 61 Revisited): This was Rolling Stone’s top song of all time, which is a fine choice, even if they were undoubtedly a little biased. The amount of hype “Rolling Stone” has gotten throughout music history should have outstripped its quality by now. But the lead track on Highway 61 Revisited is such an impeccably structured masterpiece with so much vitriol baked into its bars that its quality will always remain undeniable.


2. “The Times They Are A-Changin’” (1964, The Times They Are A-Changin’): Like “Blowin’ in the Wind”, “Times” has become overshadowed by the vast catalog that followed it. But “Times” is Dylan adopting the stance of a prophet unwelcome in his hometown, and the message he’s proclaiming has the distinction of defining not only its own era but every era since. The times indeed are changing, and we just can’t keep up.


1. “Tangled Up in Blue” (1975, Blood on the Tracks): The best Dylan song is also the saddest, the loneliest, the realest. The lyrics take some surreal turns, but by and large they concern the end of a relationship. Finding specific meanings in Dylan songs is often a fruitless exercise. He deals more in vignettes and moods than in lessons or themes, and “Tangled Up in Blue” is a myriad of vignettes all in one mood: longing. I first found “Tangled Up in Blue” while I was happy in a relationship, but I didn’t fall in love with it until I experienced some heartbreak. You can appreciate the song while you’re happy, but it won’t be until you’re broken that “Tangled” truly inhabits you.


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