10 Most Perfect Bob Dylan Songs, Ranked

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Is it a bad idea to try to single out the very best Bob Dylan songs, in turn effectively snubbing so many others that tons of people probably like? Maybe. It depends on how you define “song” just how many there are, but even if you only go by officially released singles and/or tracks from albums (so no demos, outtakes, alternate versions, or live recordings), you’ve still got hundreds of songs, and likely dozens upon dozens that are either perfect, or close to it.

Bob Dylan has just been that prolific, and what he did in the 1960s alone (nine studio albums, one of them famously a double album, too) is more impressive than what many artists achieve after numerous decades. He’s also enigmatic, at the risk of understating things, mixing things up and venturing into different genres at a pretty consistent rate. People are therefore going to find different periods of Dylan’s career more compelling than others for personal reasons. So, just take the following with lots of grains of salt. Empty out the shaker. Count the grains of salt. Then empty another shaker’s worth. Yes, about that many.

10

“The Times They Are a-Changin'” (1964)

It’s a possibly obligatory mention, but regardless, here’s “The Times They Are a-Changin’,” from the album of the same name, which was Bob Dylan’s third overall. It’s a big old anthem for the 1960s as a whole, even if the album it was on came out in 1964, when there was still half the decade left to go. It was a decade of change and stuff. That’s what those times were a-doin’.

That’s all to say that “The Times They Are a-Changin’” is almost a bit blunt compared to some of the tracks Dylan would record in subsequent years, and also, there isn’t as much to write home about here once you move beyond the lyrics. It’s simple, even if it’s also more complex than what plenty of other artists are ever capable of… it’s just simple in feel when it comes to Bob Dylan and where he was to go post-1964.

9

“All Along the Watchtower” (1968)

To address the elephant in the room, yes, the Jimi Hendrix Experience covered “All Along the Watchtower,” and it’s one of those rare and beloved covers that might well be even better than the original. And that’s a particularly impressive achievement in this instance, since Dylan’s original version of “All Along the Watchtower” is also amazing, and the song works fantastically as something a bit more subdued than that iconic cover.

It’s sparse in its sound, and then lyrically, it’s also quite ominous, and maybe even kind of mythical. There’s a joker and a thief, they journey and talk about some stuff, it’s a bit biblical, and then it’s also all weirdly unsettling, maybe partly because so much still feels up to interpretation, even with there being a surface-level narrative here. It’s not just confounding and enigmatic poetry or anything (not that there’s anything wrong with that, when Dylan does it well, at least). It’s all great, though, obviously.

8

“Not Dark Yet” (1997)

Yes, most of the songs here are from the first decade and a bit of Bob Dylan’s career, but that shouldn’t suggest his good material is only relegated to the 1960s and 1970s… more just that that’s when many of his very best songs were written and released. 1997’s Time Out of Mind, though, is his best album of the last half century, since 1976’s Desire came out at the very start of that year, and so it’s more than 50 years old now.

Time is out of mind, and time also flies. Anyway, the centerpiece of Time Out of Mind is arguably “Not Dark Yet,” which feels like it’s all about confronting mortality. It’s really effective as an introspective song, feeling like it could’ve been to Dylan what Johnny Cash’s cover of “Hurt” was to Cash, but then Dylan’s kept on trucking since 1997, releasing new music as recently as 2020.

7

“I Want You” (1966)

Blonde on Blonde is going to have two tracks appear on this ranking, and there’s only one other Bob Dylan album where that’s going to happen. Some may say that’s two too many, Charles Bronson-style, but these albums are just that good, and then also, with Blonde on Blonde, it’s a double album. It more than earns the right to be extra represented.

“I Want You” is from that 1966 double album, and it’s maybe the punchiest and most immediate track of the bunch. It’s a song about love or infatuation or a bit of both, and not a simple one if you want to dig into what Dylan’s going for lyrically. Like with a bunch of songs, there’s a lot. Or you can just enjoy it as an up-tempo (by Bob Dylan’s standards) folk rock song.

6

“Desolation Row” (1965)

Alongside Blonde on Blonde, there was the perhaps equally important Highway 61 Revisited, and that’s the other album of Dylan’s here where two tracks have been selected for the overall ranking. The first of them is the last track on the album: “Desolation Row.” This is a massive song in length, spanning over 11 minutes and being a portrait of some undesirable part of town, but the town itself isn’t specified.

There’s a lot here that’s not specified, or specific. It’s a track you can just dive into and come up with all sorts of interpretations of, with lots of small stories being told within the overall broader portrait of somewhere downtrodden. It’s not vague in a frustrating way, and the length here really isn’t an obstacle, either. If anything, it makes “Desolation Row” even easier to get lost in.

5

“Hurricane” (1975)

Narratively, “Hurricane” is one of Dylan’s most compelling songs, and perhaps his best socially conscious protest song not released in the 1960s. Actually, it might well be even better than most of those ones, too, since it’s such a sprawling song that maintains a good pace and one’s full attention for about eight and a half minutes. It doesn’t feel that long, that’s for sure.

You can’t really misinterpret or analyze this song’s meaning to a great extent. It’s “the story of the Hurricane,” so sings Dylan, with The Hurricane being the nickname of boxer Rubin Carter, who was wrongfully convicted of murder and imprisoned for nearly 20 years, which ended his once-promising boxing career. Also, “Hurricane” happens to be one of Dylan’s more thrilling-sounding songs musically, with the prominently featured violin here helping a great deal in that regard, as does the surprising energy the track has (compared to the majority of Dylan songs).

4

“Blowin’ in the Wind” (1963)

Like “The Times They Are a’Changin’,” “Blowin’ in the Wind” is an early Bob Dylan track that’s also a protest song of sorts, and it’s the better one overall, if you want to go there. Both are great, though. It’s got a bit more to unpack lyrically, while much of it is also fairly direct, and then it’s got a gentler and more compelling feel to it beyond the lyrics, musically speaking.

It might be stating the obvious, but it’s also aged surprisingly well. “Blowin’ in the Wind” does endure particularly well, and it’s perhaps the first outright perfect song Bob Dylan ever released, with the album it was from, The Freewheelin’ Bob Dylan, coming out when Dylan himself was just 22 years old. And it was, in hindsight, kind of just a hint of further (and even more groundbreaking) greatness to come.

3

“Visions of Johanna” (1966)

Of all the songs here, “Visions of Johanna” is probably the hardest to unpack with just a couple of short paragraphs. You can listen to it for yourself, maybe five or six times in a row, if you want, and try to unpack what you can out of it. The whole thing’s hypnotic and the words all sound good together, even if all the lines – though recognizable as English on their own – are hard to piece together. In that sense, it’s the track on Blonde on Blonde that best encapsulates the odd spirit and feel of the overall album.

It’s among the most mysterious Bob Dylan songs, and then of all his songs that have some element of mystery to them (or cryptic lyrics), it’s easily one of the very best. This can be said: every time you go back to it, it sounds even better. It might not make more sense necessarily, but understanding it even just in feeling or vibes-wise is something. And so many of those odd lines throughout will, once heard, likely implant themselves in your brain forever, whether you want them to or not.

2

“Like a Rolling Stone” (1965)

Even though “Desolation Row” would still make for an incredible closing track, if “Like a Rolling Stone” wasn’t featured as the opening track on Highway 61 Revisited, the album as a whole likely wouldn’t be nearly as fondly remembered. It’s like what “Visions of Johanna” was for Blonde on Blonde, with “Like a Rolling Stone” doing the best a song could in capturing just about everything in Highway 61 Revisited within a single (but still fairly long, at over six minutes) track.

It all sounds recognizably Dylan-esque nowadays, but in 1965, “Like a Rolling Stone” confounded some, to the point where it was almost unreleased. Thankfully, it did, because it then helped re-energize Dylan’s already strong music career, suggesting he had places he could go beyond the realm of the protest song, and that those places could be even more interesting. It’s easy to take the impact of this track for granted, to some extent, but if you consider the historical context and how it would’ve sounded more than 60 years ago, it’s easy to rank it high among Dylan’s greatest songs.

1

“Tangled Up in Blue” (1975)

Introspection wasn’t a foreign concept to Bob Dylan in 1975, by any means, but Blood on the Tracks still felt like something uniquely personal for Dylan, more so than any single album he’d done before then. Not according to Dylan, though. The enigma of the man continues. “Tangled Up in Blue” sets the mood for the whole album, and feels like a break-up song in a very Bob Dylan way.

Blood on the Tracks feels like a break-up album, too; Dylan doing his own Rumours a couple of years before Fleetwood Mac did. If you’re more into his folk stuff, or his songs that looked outward into society on a lyrical front, maybe Blood on the Tracks and “Tangled Up in Blue” wouldn’t rank as your favorite Dylan album and song, respectively, but if you want to see yet another side of Bob Dylan (there are many), then album and song alike are pretty astounding and eye-opening.