10 Bob Dylan Songs That Never Hit No. 1 but Became Classic Rock Masterpieces

Published Oct 16, 2026, 1:21 PM EDT

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Surprisingly, Bob Dylan has never actually had a song hit number one on the Billboard Hot 100, and so you can’t even call him a one-hit wonder by the most straightforward definition of that term, since an artist who’s a one-hit wonder will have, you know, one number one song to their name. But also, Bob Dylan’s frequently been more of an album-focused artist than a singles-focused one, and he’s also legendary without having massive hits, as should be evident to anyone who’s paid even a little attention to music for the last, what, 65 years?

Further, some of Bob Dylan’s best songs have charted, or at least received radio play, and those ones are, like, semi-hits, or at least pretty well-known without ever being number ones. That means if you want to look at Dylan’s best songs that weren’t number one, you’ve technically got all of them to choose from, but below, there’s going to be a focus on his best rock songs (that also, sure, never reached number one). Some of these are mellow, and a few are folk rock, but if a great song of his isn't here, it might be because it was too mellow or “just” folk, rather than folk and rock at the same time.

10 "Forever Young" (1974)

There are going to be a few 1970s songs up first, but don’t fear, because the 1960s will be traveled back to shortly. It makes some sense, though, because the 1960s wasn’t a decade where Bob Dylan was necessarily a rock artist for the entirety of, because his earlier albums were heavy on folk, all to the point that perhaps the defining moment of his early career was deciding to go electric (not even particularly heavy) and causing alarm in the process.

Anyway, onto the 1970s. “Forever Young” is one of Dylan’s best tracks from this decade, and it’s a very approachable laidback rock song overall. It’s also worth noting that it comes from an album of Dylan’s that isn't regarded as one of his very best, Planet Waves, but it is a Dylan album that reached number one on the Billboard 200, which is like the Billboard Hot 100, but for albums instead of songs. So, that might speak to the idea of Bob Dylan’s strength being albums more so than singles.

9 "Knockin' on Heaven's Door" (1973)

“Knockin' on Heaven's Door” did well, if you go by charts, since it hit #12 on the Billboard Hot 100 and cracked the top 10 in places like Australia, Ireland, and Norway. It was written for a pretty great (and underrated) Western called Pat Garrett and Billy the Kid, fitting in well with that movie’s solemn tone and feeling appropriate for something so revisionist (albeit not quite as devastating as Sam Peckinpah’s other big Western, The Wild Bunch).

It stands as one of the more emotional and cathartic Bob Dylan songs released up until that point.

Dylan also had a supporting role in this movie, and sure, he’s not as great an actor as he is a folk/rock artist, but he has presence in the film and definitely brings something to it. “Knockin' on Heaven's Door” on its own is also pretty great, if you want to just judge it as a song, and it stands as one of the more emotional and cathartic Bob Dylan songs released up until that point in his music career.

8 "The Man in Me" (1970)

Bob Dylan can do an earworm if he wants to, a fact that “The Man in Me” is a testament to. It’s one of the lighter and breezier Dylan songs, so ranking it among some other heavy-hitters might seem a bit eyebrow-raising at first, but if you're talking about number one songs, or at least keeping them in mind, it feels fitting to think about Bob Dylan tracks that could’ve potentially hit number one.

And, yeah, “The Man in Me” is easy to like and it would make a certain amount of sense for it to blow up and be popular enough to top the Billboard Hot 100. It didn’t, but it could’ve, and maybe even should’ve. It’s fun, and maybe some of that comes from never being able to resist associating it with The Big Lebowski, but The Dude, for all his faults, had good taste in rock music. If it’s good enough for The Dude, it’s good enough for this ranking.

7 "Like a Rolling Stone" (1965)

Since it kicks off Highway 61 Revisited, which is probably the go-to pick for “best Bob Dylan album” in the same way that Sgt. Pepper’s Lonely Hearts Club Band is the easy/expected pick for “best Beatles album,” “Like a Rolling Stone” is a song you’ve likely heard before. If you start with the man’s best album and all, or the one that you’ve probably heard is the best album, then it’s right there, and hard to avoid.

And it is a great song, not to mention a pretty perfect example of Dylan’s style of folk rock, even if it could be ever so slightly overrated? Like, sorry. It does have to be included, though, and it is very good, even if a bit unexciting compared to some of his other songs. Also, “Like a Rolling Stone” came within just one spot of being #1 on the Billboard Hot 100, charting at #2.

6 "All Along the Watchtower" (1967)

To get the obvious out of the way first, yes, the Jimi Hendrix cover of “All Along the Watchtower” does sound like more of a rock song, pushing things a bit harder, but the Bob Dylan original is still rock enough. It’s all quieter and a bit more sinister, but it pushes forward nonetheless and does make for something that’s pretty snappy and immediate by Dylan’s standards.

Further, his version is technically snappier than Hendrix’s in the sense that it’s shorter, and Dylan’s approach does mean that you focus on the lyrics a little more. And Bob Dylan… well, he can write lyrics, you know? “All Along the Watchtower” tells what feels like a pretty complete story in just two and a half minutes, so it makes sense why Dylan eventually won a Nobel Prize in Literature, honestly.

5 "Desolation Row" (1965)

Highway 61 Revisited starts strong, thanks to “Like a Rolling Stone,” and then it also ends excellently, thanks to “Desolation Row.” The former was one of Dylan’s biggest hits, and a few other songs here have been singled out for what one would’ve imagined was potential as singles, but “Desolation Row” doesn’t really feel like a traditional chart-topper, mostly because it’s very long.

At over 10 minutes, it’s the song equivalent of an epic, but hey, it’s still folk rock, and it still didn’t hit #1, so it’s fair game to be counted here. It’s worth including because it is well and truly one of Dylan’s best, especially when you focus on the lyrics, because there is an immense amount going on here narratively and thematically, even when you take into account the length of the song and the fact it’s got a lot of time/space/room to work with.

4 "Not Dark Yet" (1997)

If you listen to “Forever Young” back-to-back with “Not Dark Yet,” it’s pretty sobering, because one is thinking about aging while young, and then the other is about aging from a more mature place. It’s still not entirely hopeless or just depressing, because it’s “not dark yet” and all, but it’s all about that darkness looming, and that makes it hard to avoid engaging with, as a song, without thinking about mortality.

This might well also be the best rock (or semi-rock) song of Bob Dylan’s made after the 1970s. It’s not the case that he lacks interesting material at all in his later decades as an artist, but most of his best stuff can be found in the 1960s and 1970s. But it’s still worth venturing out to find something like “Not Dark Yet,” which matches up to his best songs from those two earlier decades quite comfortably.

3 "Sad Eyed Lady of the Lowlands" (1966)

Plenty of great things that were said about “Desolation Row” can also be said about “Sad Eyed Lady of the Lowlands,” which more than sustains itself for a duration of over 10 minutes. It’s sprawling stuff, and difficult to entirely summarize if you're looking at what it’s about lyrically. That last point might make it a bit different from “Desolation Row,” where you can comprehend a bunch of smaller stories within one massive song.

But “Sad Eyed Lady of the Lowlands” sounds great, which is the main thing, and there is something moving about it all, even if it’s hard to say exactly what it is that makes it emotional. Plenty of great songs are like that, though, and that’s especially the case for someone as enigmatic (and unafraid to be mysterious) as Bob Dylan.

2 "Hurricane" (1975)

Without a doubt, “Hurricane” is one of Dylan’s most engaging songs, and it also builds upon what he was doing in the early years of his career, when he was best known for his protest songs. It’s an elevation of that kind of thing, with socially conscious lyrics paired with something more energetic and rock in its sound, and then ambition-wise, it also goes beyond Dylan’s other protest songs thanks to its length.

As the lyrics say, it’s “the story of the Hurricane,” which Bob Dylan makes very clear, and The Hurricane was the nickname of boxer Rubin Carter, who was wrongfully convicted of murder and imprisoned for nearly two decades. It’s recognized now as a great Bob Dylan song, but wasn’t a huge seller back in 1975, only cracking the top 10 in Australia (where it got as high as #7).

1 "Tangled Up in Blue" (1975)

Blood on the Tracks, rather than Highway 61 Revisited or Blonde on Blonde, might well be the actual best place to start if you're new to Bob Dylan somehow, or at least new to his albums. It’s got an immediacy and approachability to it, thanks to it being pretty unambiguously emotional and bittersweet, albeit maybe a little more bitter than sweet. And so Highway 61 Revisited and Blonde on Blonde could well be perfect to check out second and third, respectively, if you’ve already dug Blood on the Tracks.

And the highlight of that album is “Tangled Up in Blue,” which could well be the single best song of Bob Dylan’s entire career, too. Even people who don’t like the type of music Bob Dylan tends to play will probably get something out of a song that’s just this good, and so here it is. Not a number one on Billboard, but a number one on this ranking.