Adviser’s note: Thomas Rice is no longer on our staff. With diploma in hand, he is off to bigger and better things in the real world. However, this was a labor of love for him, and though he did not quite finish it, it deserves publication. Out of 33 albums, Thomas writes about 31 in full and mentions the 32nd one. So, if you are a Dylan fan – you know what his number one album is. Enjoy!

The impetus for this was twofold. First, it seemed like an interesting thing to write about, and second, I’ve looked at the analytics for this website, and our own Lucy Samuels’ op-ed ranking Mitski’s albums gets the most clicks each and every month. Being the fiend for attention that I am, I’m trying to hitch onto that bandwagon like a new Cavaliers fan in July 2014.
Dylan has released a whole lot of albums since his self-titled debut came out in 1962, so I’ve divided them into seven eras: Folk (1962-64); Electric (‘65-66); What’s This Guy Doing? (‘67-73); Renaissance (‘74-78); Christian (‘79-81); What’s This Guy Doing? (Redux) (‘83-90); and Renaissance (Redux) (‘97-2020).
I’ll elaborate more on what each era entails later, but these are the Cliff Notes:
Folk- Folk songs. Political.
Electric- Rock! Not political generally. Our guy gets crazy famous.
What’s This Guy Doing?- Sometimes great, sometimes not. Seems the genius might be fading.
Renaissance- Not fading! Definitely gonna keep making classics forever!
Christian- Never mind. These are about God mostly.
What’s This Guy Doing? (Redux)- Maybe the genius has faded. “Oh Mercy” is good, though.
Renaissance (Redux)- Not faded! He’s sounding real old, though.
Last thing before the list: I’m only counting studio albums that feature original songs (with one notable exception). This isn’t discounting having any covers, but they can’t be the whole album (again, except for one record), so there is no “Dylan,” “World Gone Wrong,” or “Triplicate.” Quite frankly, I just don’t much care about the songs Dylan didn’t write, and none of the covers I’ve heard particularly interested me.
These parameters also disqualify any of “The Bootleg Series,” a collection of compilations that feature previously unreleased takes of both released and unreleased songs. A lot of these are good, they just don’t really count as albums, and volumes’ duration can be in excess of six-and-a-half hours, so I’m vetoing them.
With that out of the way, on to the list.

Part I: The Worst
This first group is characterized very specifically: I think any of these could end up last on this list. I settled on one, but each of these three albums is uniquely terrible and could take the bottom spot on the right day, so congrats to them for that.

33. Down in the Groove (1988)
What’s This Guy Doing? (Redux)
I landed on “Down in the Groove” as the worst, not because it’s aggressively bad, but rather because it isn’t. The album’s main issue is that it isn’t really anything, unlike the two albums that I ended up ranking above it. Those have things about them that I dislike, that really make me feel like I don’t want to listen, while “Down in the Groove” just makes me forget anything’s playing, with some quick flashes of being truly horrible.
To be a bit more precise, “DITG” epitomizes a lot of things that made the 80’s Dylan so disappointing. Half of the songs are mid- to low-tempo ballads that use their bland, slow instrumentation to great effect by putting me to sleep. The other five tracks are faster and louder, but they also manage to fade into the background, except when Dylan tries a bit too hard to sing. (This is a pervasive issue with his “What’s This Guy Doing? (Redux)” era. I am a defender of Dylan’s voice, even in his later years, as interesting and eccentric rather than irritating, but the 80’s were not kind to his vocal cords, and someone should have told him that at the time.)
This isn’t even mentioning the fact that most of the tracks on this album weren’t even written by Dylan, and I’ll just assert here that while his songs have had very inspired covers (“All Along the Watchtower”), Dylan does not make good covers, and he never really has. This is evident in the bland covers on this album, none of which are worth more than one listen.
To be completely fair, “Silvio” is a real high point for the album. It’s the only track that actually has a “Groove” I can get behind, probably thanks to Robert Hunter of the Grateful Dead, who co-wrote it. It’s the only song that makes you feel its presence, and it’s one of Dylan’s best works from the 80’s. Listen to this song. Don’t listen to any of the rest of “Down in the Groove.”

32. Saved (1979)
Christian
The rest of Dylan’s Christian albums will come up in this list very soon, but the sophomore gospel effort, “Saved,” has to be the worst. It has similar problems to “Slow Train Coming” and “Shot of Love,” like the fact that Dylan’s voice was really fading despite his attempts to put more power into his singing and an oddly aggressive and bitter tone for an album that’s supposed to be about praising God, but it also has more uninspired instrumentals than either of those two albums. It’s kind of the “Down in the Groove” of the Christian era, in that sense.
I think the main pitfall that comes with Dylan’s transition to religious music is his inability to then write interesting lyrics, or perhaps more accurately, interesting lyrics that also are good. I mentioned it earlier, but throughout this era, Dylan was weirdly accusatory and passive aggressive towards everyone, sort of like he’s now qualified to judge people since he found Jesus. Great religious albums have been made, but Dylan kind of makes these about himself, and it gets a little embarrassing.
There’s a little solace to be found, though, even if it comes with caveats. I like the tune of “Covenant Woman,” though its lyrics are rather obnoxious, and the title track features good energy with a more “praise God” message rather than a “um, maybe you could be an actually good person like me if you praised God a bit more” message.

31. Self Portrait (1970)
What’s This Guy Doing?
If I were to choose one album that I hate the most, this would be it. It makes me much more upset than anything else found here, and it isn’t particularly close. It’s just so inconsistent, so long (74 minutes, and you feel every second of it), and it likes to do little things to stop me from forgiving it, because there is objectively a lot of good here that is frequently overshadowed by the bad and the absurdly terrible.
Let’s start with the good: “The Mighty Quinn,” “Days of ‘49,” “Gotta Travel On,” and both “Albertas” are all worthwhile, good songs, even if they don’t live up to much of Dylan’s 60’s output and fall nearer “‘Nashville Skyline’ good” than “‘Blonde on Blonde’ good.” There’s also a nice live version of “She Belongs to Me” that I quite like.
Now, negatives:
The album kicks off with “All the Tired Horses,” which just has a chorus repeat the same two lines for three minutes straight. If I were to erase one thing from existence, it might very well be this song.
Dylan uses his stupid Kermit the Frog country voice a lot. Don’t do that. It barely works on “Nashville Skyline,” and here it makes me want to throw my speaker into the nearest ocean.
There’s an instrumental track called “Woogie Boogie.” It’s not really as bad as it sounds but it’s still called “Woogie Boogie.”
I have not yet heard anyone butcher a song as much as Dylan does on the live version of “Like a Rolling Stone,” and that’s his own freaking song. Not only is Kermit singing it, Dylan decided to take away all the ire and derision that makes the original version one of the greatest songs ever, instead making the track flat, boring, and an utter travesty. It’s playing as I write this and I want to smash my laptop with a baseball bat.
“Wigwam” is just horrible vocalizing. I hate it so much. It makes me so angry that I can’t think of another example of me breaking things to illustrate my rage.
The album cover sucks and not in a fun way.

Part II: Real Bad
I think I put all of these, which include both simply bad albums and oddities, together because they are all better than the worst, but I nonetheless don’t really want to hear them again.

30. Under the Red Sky (1990)
What’s This Guy Doing? (Redux)
“Under the Red Sky” suffers from an affliction we can call “‘Down in the Groove’ Syndrome.” It has basically the same issues as that album, except I give it more points for being totally insane sometimes. “One day the little boy and the little girl were baked in a pie,” proclaims the title track. It doesn’t make any more sense in context.
There are a lot of candidates for Dylan’s worst song. I’ll get to a lot of them, and I’ve already expressed my hatred for “All the Tired Horses,” but “Wiggle Wiggle” is a very, very strong choice, and it actually features Dylan singing, too. He just sings the word “wiggle” a lot, and then proceeds to outline the situations in which one should wiggle. It’s not something that I enjoy listening to.
I enjoy “T.V. Talkin’ Song,” ”Unbelievable,” and “God Knows,” but they’re still pretty minor highlights. That’s another problem; in Dylan’s other work from this era, he would at least crank out a song or two that reminded you how good he could be. Even “DITG” had “Silvio.” “Under the Red Sky,” though, doesn’t have anything like that, which prevents me from appreciating its absurdity more.

29. Slow Train Coming (1979)
Christian
I wish this train were a bit faster. “Slow Train Coming,” though, feels a lot longer than its actual 46-minute length. It has all of the issues of “Saved,” except it does spare a bit of the blandness.
This album actually kicks off pretty strong, with “Gotta Serve Somebody,” maybe Dylan’s second best religious song, and “Precious Angel.” John Lennon famously hated “Gotta Serve Somebody,” but I think I can get behind its spacy synths, even if the lyrics are a bit assuming. “Precious Angel” just has a nice tune, which isn’t uncommon here. In fact, there’s a lot of residual goodness in the songs, stemming from Dylan’s 1978 effort, “Street Legal,” which places far higher on this list.
The music is just so often overshadowed by lyrics that just make you feel like you’re being judged constantly, I can’t get over it.
For its entry in the “Worst Bob Dylan Song” competition, “Slow Train” has “Man Gave Names to All the Animals,” which, to be fair, delivers on its central conceit. It very much does explain what animals are and what they are called. I can’t really do anything but show you the first verse:
He saw an animal that liked to growl
Big furry paws and he liked to howl
Great big furry back and furry hair
Ah, think I’ll call it a bear
This continues for four-and-a-half minutes. The song culminates in an allusion to the snake in the Garden of Eden. Deep. You can tell it’s a snake because the second-to-last line ends in the word “lake.” Such artistry.

28. Christmas in the Heart (2009)
Renaissance (Redux)
I said that there was one fully-covers album featured in this list, and this is it. I figured this was far, far too odd to leave off the list.
What is “Christmas in the Heart?” I think the most reasonable explanation is that it’s an easy-to-make charity album released in an era when Dylan really started liking his covers records. It seems like maybe he just wanted to make this, so he did.
But it’s just so weird. It’s so weird hearing a Christmas album from someone who hasn’t really been able to sing very well for a few decades. It’s weird that the album features no new material, except some lyrical changes to “Must Be Santa.”
Oh, man, “Must Be Santa.” What a track. Dylan just rambles his way through the accordion-led instrumental, and changes one verse to this:
Dasher, Dancer, Prancer, Vixen
Eisenhower, Kennedy, Johnson, Nixon
Dasher, Dancer, Prancer, Vixen
Carter, Reagan, Bush, and Clinton
Why? Great question. There’s a music video for this song, because of course, and it’s one of the most ridiculous things I’ve ever witnessed, featuring maybe the most inaccurate lip syncing I’ve ever seen.
The rest of the album isn’t very memorable, though. I always thought Dylan’s backing band sounded a little too Christmas-y throughout the 2000’s, though, so the backing fits the yuletide spirit.
I think my thoughts on this album boil down to this: I’m glad it exists, but I don’t really want to listen to it. This is contrary to the albums below it, which I don’t want to listen to and I would prefer them not to exist.

27. Pat Garrett & Billy the Kid (1973)
What’s This Guy Doing?
The oddities are clearly the hardest for me to place on this list. I just don’t know what to do with “Pat Garrett & Billy the Kid.” First, it’s a movie soundtrack, which is unique for this list. From that, it’s also mostly instrumental, except for “Billy 1,” “Billy 4,” “Billy 7,” and one of Dylan’s most famous songs, “Knockin’ on Heaven’s Door.”
That’s another complication with ranking it: It kind of all fades into the background compared to the one mega-hit that every beginning guitar player learns. The instrumentals aren’t bad, but they’re not great, either, though they’re probably better in the context of the movie.
I think the reason this falls so low on the list, despite my liking for most of the tracks, is that I just don’t love “Knockin’ on Heaven’s Door” all that much. It’s a good song, but I don’t think it would have stood out much alongside Dylan’s 60’s catalog, and Dylan even wrote a better song with “heaven” in its name and with a similar sentiment in 1997’s “Tryin’ to Get to Heaven.”

Part III: Alright
This next group is just albums that I’m not willing to call good, but they’re not too bad, either. Some of these are good enough to listen to all the way through, and some just have some good highlights, but there’s always enough redeeming quality for me to give it a listen.

26. Together Through Life (2009)
Renaissance (Redux)
This is ending up as the lowest rated of Dylan’s second Renaissance era, and I think that’s because it exemplifies the worst parts of Dylan’s later work. The bluesy instrumentals are pretty bland, none of the lyrics particularly grab me, and Dylan can’t perform like he did earlier in his career.
Overall, I just think this album is kind of boring, while being clearly overshadowed by Dylan’s other original 21st century releases.
There are highlights, like “Forgetful Heart,” “I Feel a Change Comin’ On,” and “It’s All Good,” but songs like “My Wife’s Home Town” do nothing but bore me and sour me on the album as a whole.
As a note, this album cover is absolutely horrible, which is a commonality in the “Renaissance (Redux)” era. I don’t know why, but every record after “‘Love and Theft’” has an ugly stock image on it, and even the best of them, “Tempest” doesn’t look good.

25. Knocked Out Loaded (1986)
What’s This Guy Doing? (Redux)
I really want to judge these holistically as albums. That’s what I’m trying to do here. “Knocked Out Loaded” makes that very, very hard. On one hand, the first half of the album is terrible. “Down in the Groove” type of bad. The second half, though, is some of the best music Dylan has made since the 70’s.
I’m going to be very complimentary for the rest of this section, so keep this in mind: the first half of “Knocked Out Loaded” is very, very bad, even though I’m not going to discuss that, and it places this low for a reason. Go back to “Down in the Groove,” most points I make there apply to the first half of this album.
The second half of “Loaded” features three songs, all co-written by Dylan and one other person. The latter two, “Got My Mind Made Up” and “Under Your Spell,” co-written by Tom Petty and Carole Bayer Sager, respectively, are both good tracks that stand far above most of the songs from this era.
The first song on side two, though, is “Brownsville Girl.” The 11-minute epic is one of Dylan’s best songs ever, full stop. It’s absurd and unfocused and rambling and expansive and absolutely incredible. It sees Dylan going back to being the Dylan from his prime: writing lyrics that are absurd and convoluted while remaining coherent and plain. It’s the “Stuck Inside of Mobile with the Memphis Blues Again” of the 80’s. It’s about a relationship, and a Gregory Peck movie, and a road trip, and being an outlaw, and about a hundred other things. It’s gold from start to finish, and packed with the kind of memorable lines that are glaringly absent from a lot of Dylan’s mediocre output. Some of the best lines:
“She said, ‘Even the swap meets around here are getting pretty corrupt’”
“‘Turn him loose, let him go, let him say he outdrew me fair and square
I want him to feel what it’s like to every moment face his death’”
“I would have gone on after you but I didn’t feel like letting my head get blown off”
“I didn’t know whether to duck or to run, so I ran”
“Now I’ve always been the kind of person that doesn’t like to trespass but sometimes you just find yourself over the line”
“I don’t have any regrets, they can talk about me plenty when I’m gone”
It helps that “Brownsville Girl” takes up almost a third of this record, its length in this case using the positive side of a double-edged sword. I love a lot of Dylan’s longer songs, but they can hurt an album severely if there’s a 10-minute black hole in the middle of the record. “Brownsville Girl” justifies its length and saves this record from languishing among the dregs of Dylan’s output.

24. Shot of Love (1981)
Christian
More like “Shot of Hate.” That isn’t to say that I hate this album, but Dylan seems angrier than he has ever been on these songs, which, again, is pretty odd for a gospel record.
This is the highest ranked of any of the Christian albums on this list, and it’s no coincidence that it’s also the most secular of any of them. Its main highlight is “Every Grain of Sand,” which is gospel, but it’s more vague about its religiosity than more preachy songs. I also like the more aggressive “The Groom’s Still Waiting at the Altar,” which possesses more energy than any track on “Slow Train” or “Saved.” “Heart of Mine” is another highlight, and displays that vague religiosity. It could be interpreted as religious, but it could also just be generally about heartbreak. This is a lot of what makes “Shot” so palatable, as the purely Christian songs are mixed in with secular ones.
There are some odd moments, too, like a tribute to comedian Lenny Bruce aptly titled “Lenny Bruce.” It’s just a colossally weird track, and isn’t the only tribute that Dylan has done that flummoxes me. It’s also slow and pretty bad, I don’t recommend.

23. Infidels (1983)
What’s This Guy Doing? (Redux)
“Infidels” was, despite its relatively low place on this list, generally a return to form from Dylan. It’s a natural advancement from “Shot of Love,” being completely secular even though it incorporates copious biblical references. At times, it sort of shows you what Dylan could’ve done with his Christian albums, had he not written the lyrics so blandly.
Perhaps even more than “Shot of Love,” “Infidels” serves as a follow-up to Dylan’s final nonreligious album of the 70’s, “Street Legal.” On “Infidels,” as was the case on “Street Legal,” he works to create vivid imagery that feels epic while often simultaneously being inscrutable. It makes for great-sounding lyrics, if not always for the most affecting ones. The best example of this is the opener, “Jokerman,” the best song on the album. It’s about the title figure, who … is and does a lot of things. It’s essentially impossible to break it down further. I’ve seen people try, saying the “Jokerman” is Jesus, or Ronald Reagan, or Dylan himself. (The internet will say any figure in a Dylan song represents himself. It’s probably not too far off a lot of the time, but it’s a very noticeable trend.) Songs like “Jokerman” don’t really need to make sense, though, because the allusions and imagery just kind of wash over you, aided by one of Dylan’s catchier tunes. “Tight Connection to My Heart,” the closer, also has a strong tune and feels more like it’s a preview to “Empire Burlesque’s” 80’s pop vibe.
When you can understand the lyrics, it’s a bit confusing. Dylan didn’t leave all his Christian idiosyncrasies behind, because a lot of “Infidels” is concerned with the doom and gloom of global society, except instead of blaming a lack of worship, Dylan doesn’t really blame anything. Tracks like “Union Sundown,” which complains about a lack of American-made goods available, like he’s on ABC Nightly News, and “Neighborhood Bully,” which comes out as vehemently pro-Israel, are just kind of angry laments. Dylan doesn’t really bother to treat the issues with the care he seemed to earlier in his career. He’s clearly looking for important topics, but his points are usually half-baked, uninteresting, or both. The chorus of “Man of Peace” proclaims that “sometimes Satan comes as a man of peace,” but it’s kind of unclear what he’s talking about exactly, so it comes across kind of pro-war, as does a lot of this album, except the song “License to Kill,” which seems directly against war. It’s entirely confounding.
That isn’t even to get into “Sweetheart Like You,” which is maybe about the church, but the extended metaphor of talking to a woman at a bar leads to weirdly misogynist moments, like the lines “You know a woman like you should be at home/That’s where you belong/Taking care for somebody nice.” To his credit, I don’t really think Dylan intended those lines to come off the way they do in context, and Mark Knopfler and Mick Taylor provide excellent guitar work on the track, so that’s something.

22. Empire Burlesque (1985)
What’s This Guy Doing? (Redux)
Here’s my primer for “Empire Burlesque:” there are at least three instruments that should not appear on each track, and yet they do. It’s pretty out-of-character for a songwriter who started his career as a folk singer. About two minutes into each song, you probably think you’ve had it figured out, with probably some combination of loud gated drums, acoustic and electric guitars, synthesizers, piano, and background and lead vocals in the mix, and then: BAM, you hear the big orchestral string arrangement. That literally happens on “Emotionally Yours,” and I laughed out loud the first time I heard it.
That’s kind of the strength and weakness of “Empire:” it’s just so big, all the time. In that way it’s oddly poignant as an 80’s album; that was the decade where pop music sounded huge all the time. Dylan produced a lot of this himself, but I think it’s very notable that Arthur Baker, who had previously worked with New Order, was also brought in. You can hear those big layerings of synths and drums from “Power, Corruption & Lies” everywhere on this album, even if they often take a backseat to the guitars and vocals.
I placed this as the best of the “Alright” albums, and it’s just because I think Dylan was putting energy into the music, and focusing it on the right things. “Empire Burlesque” is by no means perfect, and it’s too gaudy to really even be called good, but sometimes it’s just way too interesting to ignore, and that’s a win. I understand how someone could call this the absolute worst Dylan album, because it is sometimes not just “not good,” but “in-your-face bad,” (I cannot stand “Something’s Burning, Baby”) but, again, at least this is always something.
I feel the need to add a quick note regarding “Dark Eyes,” which is both the best song on the album and completely disparate from everything I’ve said so far. It’s a slow, quiet folk song, featuring only Dylan’s vocals, harmonica, and guitar. It’s an odd departure from an odd departure of an album, and even though I do appreciate the maximalism of the rest of the album, maybe Dylan should’ve gone back to his roots in this decade. It probably would’ve been good for him.

Part IV: Pretty Good
These albums are generally gonna be worth a listen, but they’re not absolutely top-tier, and each has distinct flaws. Nonetheless, we’re now getting to the good stuff.

21. The Basement Tapes (1975)
Renaissance
Some people go nuts for “The Basement Tapes.” I don’t really get it. I said that I wouldn’t include any of the Bootleg Series on this list, but in a lot of ways this was the first volume. It’s a collection of tracks recorded during Dylan’s hiatus in 1966 and ‘67 by himself and The Band, who were made up of members from his former touring band, but it’s not really a true album.
This was never really made to be listened to all at once, and it was basically only released because unofficial bootlegs were around for years. While I like basically every track individually, they kind of run together. They’ve all got country rock instrumentals with usually Dylan,but sometimes Levon Helm or Richard Manuel, singing mostly nonsensical lyrics. Again, it’s fine, and I don’t want to sound too negative, but it’s almost eighty minutes long.
It doesn’t help that there was actually much, much more material from these sessions that went unreleased, and some of it was better than even the best tracks (“You Ain’t Goin’ Nowhere,” “Odds and Ends,” “Don’t Ya Tell Henry”) from the official release. Dylan classics like “Quinn the Eskimo” (otherwise known as “The Mighty Quinn”), “I Shall Be Released, and “I’m Not There” were recorded, but are absent from this album, which is another indictment on its length.
Still, I think “The Basement Tapes,” at its core, is pretty good, even if it isn’t the best album experience.

20. Nashville Skyline (1969)
What’s This Guy Doing?
I honestly went into “Nashville Skyline” expecting to hate it. I was pleasantly surprised. I had heard “Lay, Lady, Lay,” and man, that Kermit the Frog voice Dylan uses was just a bit too much. That’s still the thing that really holds this album back, in addition to some pretty uninteresting lyrics, but I can usually get over it enough to just enjoy the country rock.
Dylan recorded the album in its title city, recruiting veteran country musicians, and I think it paid off in a lot of these instrumentals. I think the fact that “Nashville Skyline Rag,” which features no vocals, is even at all solid speaks to that. “To Be Alone with You” has a great groove, and isn’t the only song on the album that just sounds fun, and “fun” isn’t often a term that can be used to describe Dylan tracks.
Beyond the basic tone of the voice, which I cannot stress enough, is indeed very bad, I think what keeps this album down is the fact that none of it really sticks with you. Dylan doesn’t give any really poignant or emotional performances, none of the lyrics are great, and the songwriting in general is more consistent and solid than it is great.
The best-written of all of the songs is “Girl from the North Country,” which is a rerecording of one of Dylan’s best early folk songs, this time as a duet with Johnny Cash. Dylan and Cash on the same song should feel like a big deal, but it doesn’t live up to Dylan’s original recording in really any way.

19. Modern Times (2006)
Renaissance (Redux)
I think a lot of similar things about all of Dylan’s 21st century output, and I’ve mentioned a few of them already. I like the songwriting Dylan brings, specifically clearer and more thought out focuses of tracks, I like that he’s found a nice balance between instrumentals that very much fit him but aren’t boring, and I like that he doesn’t often try too hard vocally, but allows himself to talk-sing through most songs.
That being said, I slightly prefer most other “Renaissance (Redux)” releases to “Modern Times.” Honestly, it’s mostly because of the other albums. Each of those has stronger and more distinct highlights, while “Modern Times” is just uniformly pretty good, if also probably the most same-y of the bunch.
Another theme with newer releases: I like quicker songs, such as “Thunder on the Mountain,” which allows Dylan’s voice to take less of a musical load, while slower songs like “When the Deal Goes Down” can be a bit of a slough on account of the frailness of Dylan’s voice as he passed his 65th birthday. On this account, “Modern Times” is credited, as it doesn’t have too many real snoozers, but sometimes the bluesy instrumentals run together anyway, more so than on other records in this era
18. “Love and Theft” (2001)
Renaissance (Redux)
I have similar thoughts on “‘Love and Theft’” as I do regarding “Modern Times,” except “‘Love and Theft’” has some pretty clear advantages. Dylan’s voice is better, songs like “Tweedle Dee & Tweedle Dum,” “Mississippi,” and especially the absolutely fantastic “High Water (For Charley Patton)” are better than anything on “Modern Times,” and the instrumentals are generally more varied, which keeps this album both very consistent and not boring.
I really like Dylan’s entire delivery on this album, probably more so than anything he’s released since. Some of my favorite Dylan vocal lines are on this album, like the completely flustered and out-of-pattern “She says, ‘You can’t repeat the past,’ I say, ‘You can’t?/What do you mean, you can’t, of course you can!’” on “Summer Days” and the almost growling delivery of “It’s rough out there/High water everywhere” on “High Water (For Charley Patton).”
I guess I just see “‘Love and Theft’” as sort of less special than Dylan’s two latest albums, which will come soon on this list, even if at times I think it’s good and consistent enough to be placed as high as the low teens. That’s what I’ve started realizing at this point in the list: each of these records is good enough that I feel it’s a disservice to rank them this low.

17. Tempest (2012)
Renaissance (Redux)
In a lot of ways, “‘Love and Theft’” is a better album than “Tempest.” The only 2010’s album on this list is peppered with flaws, but I appreciate them too much to count it down too much for them.
A lot of the things that make this album a bit of a slough are the same things that make it utterly fascinating, and they’re largely found in the last three songs. There’s the nearly 14-minute title track, which is an epic about the sinking of the Titanic. Sure, why not? “Tin Angel” is over nine minutes, and ends with a woman cheating on her husband, her husband appearing, the other man shooting the husband, the woman shooting the other man, and then the woman killing herself. It’s a lot.
I mentioned that Dylan has some odd tribute songs. If you were told he did one for a Beatle, which would you assume? Would it be the one who had most recently died, Dylan’s fellow Wilbury, to whom Dylan had given “If Not For You” for his first solo record? Surely it would be George Harrison. Nope, “Roll on John” is a tribute to John Lennon, who had died over 30 years before “Tempest” came out, the second Beatle to perish, preceded by Paul McCartney in 1966. I’m not saying Dylan wasn’t well within his rights to write about Lennon, but it’s a profoundly odd choice with exceedingly odd timing.
“Tempest” isn’t just an oddity, though. It’s ranked this high largely because its aesthetic is perhaps the best Dylan ever crafted. There’s a distinct Vaudeville kind of attitude to the entire album, with darker and creepier tracks like “Tin Angel” and “Scarlet Town” being highlights. Here’s a note: if you have a low or gravely or generally unusual voice, try making spooky music. It worked for Nick Cave, it worked for Tom Waits, it worked for David Byrne, and man, does it work for Dylan. The fact that he can’t really do more than scratchily talk-sing very much helps the air of mystery.
“Tempest” is also aided by the fact that, apart from the creepier-sounding tracks, it has some catchier, more upbeat songs, like “Duquesne Whistle” and “Early Roman Kings.” Specifically on “Early Roman Kings,” Dylan has a kind of swagger that sometimes crops up in his newer material, and is always welcome.

16. Bob Dylan (1962)
Folk
This is another record that’s harder to place. Firstly, debuts are always different sorts of records than everything else, but this is another album made almost entirely of covers, so I don’t know exactly how to gauge its merits.
To their credit, the covers themselves are rather good, especially compared to his later ones. Dylan’s performance is actually incredible on this record, and it’s the only album where I’d argue Dylan’s performance shines more than his songwriting, even with the caveat that he only wrote two songs. Dylan has a kind of detached ire to much of his 60’s catalog, but on “Bob Dylan,” he’s noticeably more directly angry and passionate, like on “In My Time of Dyin’” and “Fixin’ to Die.” (A lot of these songs are about death, but I’m attributing that to the fact that a lot of folk songs are like that rather than Dylan’s specific choices.)
This is the first album from the “Folk” era that crops up on the list, all of which have essentially exclusively guitar, harmonica, and vocals on each song. I wouldn’t say any of the non-vocal performances are great, although they’re perfectly alright. Dylan was never the greatest guitarist in the world, but I think his playing and the parts he wrote improved greatly on his next album.
Dylan did write two songs on this record, and they’re probably the two best songs. “Talkin’ New York” has some great lines, like, “New York Times said it was the coldest winter in seventeen years/I didn’t feel so cold then.” It exemplifies the “talking blues” style Dylan would continue to use, with rambling, witty lines coming one after another, interspersed with short harmonica sections. “Song to Woody” is a more serious, personal song, written to Dylan’s idol Woody Guthrie. It’s a look into the younger Dylan’s perspective, and I think it’s at the very least maybe the most earnest song he ever wrote. It showcases a talent for poignant poetry that would later give him his iconic status as a folk singer.

15. Rough and Rowdy Ways (2020)
Renaissance (Redux)
I think a lot of “Rough and Rowdy Ways” placing so high on this list might stem from my own biases. In terms of listening all the way through the record, this one can get a bit tedious, certainly more so than the 36-minute-long “Bob Dylan.” The reason this one is placed higher, though, is because the highlights get higher, probably more so than any album in this grouping.
“RARW” kicks off with the slow, contemplative “I Contain Multitudes,” which muses upon Dylan’s fame and legacy more directly than he ever has before. That is a general theme on the album; “False Prophet” and “Goodbye Jimmy Reed” also largely concern themselves with Dylan’s career and place in the public consciousness with a greater amount of swagger than “I Contain Multitudes.”
Easily the best song on the album, though, is “My Own Version of You,” Dylan’s adaptation of “Frankenstein,” where he describes the process of creating someone from leftover parts. I think there’s probably a metaphor in there about making the perfect person for you, but I generally just appreciate the spookiness. It’s probably the most directly spooky song Dylan has written, and again, that’s a very very good thing, with descending guitar lines lending an ominous atmosphere to Dylan’s maniacal lyrics.
The biggest blemish on “Rough and Rowdy Ways” is “Key West (Philosopher Pirate).” People go crazy for this song. I cannot stand it. It’s nearly 10 minutes long in all its slow, accordion-y glory, and it just goes on and on and on. It feels significantly longer than the album’s closer, “Murder Most Foul,” which clocks in at almost 17 minutes. Dylan repeats the words “Key West” so many times, I remember his exact pronunciation anytime I encounter the phrase, which is remarkable considering I haven’t even listened to the song that many times.
There’s kind of a sense of purpose on each track on “RARW,” though, apart from “Key West,” and that’s generally what I like about it. If “Tempest” has one thematic flaw, it’s that Dylan doesn’t really seem to have as much specifically to say. “Rough and Rowdy Ways,” though, is different, so even songs that I don’t necessarily love, like “Black Rider” and “I’ve Made Up My Mind to Give Myself to You” (horrible name for a song, he clearly only called it that so it wouldn’t be confused with “Got My Mind Made Up”), have their place on the album.
Small thing: this album cover sucks so hard. It’s horrible. I saw Dylan at the Fox this year, went to buy a t-shirt, and lo and behold, the tour shirt just has the album cover on the front. I bought a “Rolling Thunder” shirt instead. Best decision of my life.
Part V: Very Good
I could also just call this “The Morass Around Number 10.” All of these albums are really close, and we’re now getting into the ones that I will listen to all the way through semi-regularly. They still aren’t perfect, but almost every song on almost every one of these albums is pretty good from here on out.

14. Another Side of Bob Dylan (1964)
Folk
This very well may be the most consistent album in this section in terms of quality, but it lacks … something. That might be the best way to put it.
Here’s a bit of a hot take, and something that may disqualify me from talking about this subject: I think pure folk music is a little boring a lot of the time, unless there’s some specific quality to make it not so. I just think a rock song can be plain, but still good, but folk songs need a little something to make me interested beyond average guitar arrangements and somewhat well-crafted lyrics.
This isn’t to say that I find “Another Side of Bob Dylan” boring (it still has exceptional things, like Dylan’s vocals and lyrics, that hold it up), but I just find it more boring and tedious than Dylan’s more well-crafted previous two records. It lacks something to make it its own album, really, as opposed to basically everything else Dylan made in the 60’s. I suppose that most of these tracks are sobering love songs, but then again, Dylan had made plenty of those before, just maybe not at quite this frequency.
I don’t want to sound too harsh; I really do love some songs on this record, and almost all the others are good. “My Back Pages” is an interesting meditation on the arrogance of youth, “It Ain’t Me Babe” functions as a blunt metaphor for Dylan’s relationship with the folk movement he would soon betray, and “I Don’t Believe You (She Acts Like We Never Have Met)” is one of Dylan’s most fun-sounding folk songs, in contrast to its bitter lyrics.
Back to my undue bashing: “Ballad in Plain D” is just plain uncomfortable. It’s about one of Dylan’s relationships, and he didn’t have to go into that much detail. It’s not fun to listen to, and you have to listen for over eight minutes.
I’m serious, though, I like this album, I promise.

13. Oh Mercy (1989)
What’s This Guy Doing? (Redux)
You may notice that this stands far, far above any other album from the 80’s. How exactly “Oh Mercy” came out between “Down in the Groove” and “Under the Red Sky,” I don’t know. Dylan just saved up all his good stuff, I guess.
I’m being a little facetious. “Oh Mercy” isn’t all that good, though I did have it all the way up at 10 at one point. The issue is, again, consistency. This might have the greatest disparity between good songs and not good songs apart from “Knocked Out Loaded,” and there’s no stylistic consistency, either.
In terms of quality consistency, this is “Knocked Out Loaded” in reverse. The first side of the record features five songs. Four are great, clearly the best four on the record. The other, “Where Teardrops Fall,” isn’t very good, but it’s unobtrusive enough to be excusable between its superior neighbors. Side two is fine, but ultimately inconsequential. I have a tough time getting through this whole album, because after “Most of the Time,” there’s only “What Was It You Wanted” to look forward to. The songs aren’t bad, just a letdown after the beginning. I remember listening to “Oh Mercy” for the first time, and I thought it was going to be ridiculously good about 20 minutes in, good enough to get near the top five on this list, but then it just leveled off, and most every passing minute disappointed me a little more.
The great songs don’t even have any consistency. Like I mentioned earlier, there are four great songs: “Political World,” “Everything Is Broken,” “Ring Them Bells,” and “Man in the Long Black Coat.” Now, all of these do share the commonality of lamenting the world’s ills and evils, but otherwise, they’re entirely unique.
“Political World” and “Everything Is Broken” are more of Dylan’s 80’s run of high-energy doom and gloom tracks, but they are the best and most high-energy of that group.
However, “Ring Them Bells” is slow, quiet, and rather hopeful, or at least trying to be hopeful, sounding opposite to the up-tempo songs.
“Man in the Long Black Coat” is yet another departure, being a prime example of Dylan’s spookiness paying off. It’s pretty similar to “My Own Version of You” in atmosphere. It clearly influenced Nick Cave & The Bad Seeds’ 1994 song “Red Right Hand,” and it would fit right in next to that track on “Let Love In,” which is a very good thing.

12. New Morning (1970)
What’s This Guy Doing?
If there’s one album on this list that fits its title best, it’s probably “New Morning,” the much-needed bounceback following “Self Portrait’s” disastrous start to the 70’s.
Dylan ditches his country voice that he acquired on “Nashville Skyline,” and in doing so gets back on track to his eventual true bounceback later in the decade.
In a lot of ways, “New Morning” mirrors “Nashville Skyline,” which came out only a year and a half earlier. They’re the two shortest records Dylan had put out to that point (though “Skyline” is almost ten minutes shorter), but they’re also both generally pretty simple lyrically, unlike Dylan’s earlier material.
Looking at these albums now, the voice really does a lot of work. “New Morning” feels like more than the sum of its parts because Dylan’s songs and performance carry a particular feeling all the way through, and the lifeless Kermit the Frog voice can’t do that.
If anything, “New Morning” is a relentlessly happy record, which is something you can’t often say about Dylan’s work. Most of his songs have at the very least a wariness or level of depth to their joy, if it’s even there, but Dylan actually just seems to be in a good place on “New Morning,” be it on the exuberant title track, the contented “If Not for You,” or even the nostalgic and optimistic “Time Passes Slowly.”
“New Morning” has its flaws, too, obviously. Some may point out that “If Dogs Run Free” is one of the most idiotic sounding things anyone has ever made. I don’t know. I think it’s hilarious in a very good way, with some very nice piano and guitar parts backing what might be Dylan’s weirdest delivery ever, accompanied by puzzling scatting. It is at the very least incredibly interesting, I’ll say that.
Now, I think “Winterlude” sucks, because it isn’t quite stupid to be funny or particularly interesting, it is merely annoying. “Winterlude, this dude thinks you’re fine” is just an awful line, and it’s essentially the chorus.
I think similarly about “Winterlude” as I do about “Father of Night,” though the music more than the lyrics does it for me on that one. I can see what “Three Angels” was going for, but on the whole, I don’t think the lyrics justify the spoken word delivery as much as Dylan thinks they do.
Luckily, all of these flaws make up only a short segment of this short album, and again, much of those actually interest me, so they aren’t even big detractions.

11. Street-Legal (1978)
Renaissance
“New Morning” was Dylan’s first good album of the 70’s, and “Street-Legal” was his last. This very well may be the album that ended up the highest compared to where I thought it would, but I just keep on coming back to it.
First things first, “Street-Legal” kicks off with not only one of Dylan’s best songs from the 70’s, but one of his best ever. From the point when “Changing of the Guards” fades in, you feel an ever-present momentum, buoyed by the horns and gospel-inspired background vocals Dylan has all across this project, as well as some excellent organs. As I mentioned in regards to “Infidels,” the lyrics of “Changing of the Guards,” and on most of the rest of the songs on the album, are more vaguely epic than they are deeply affecting. (See: seemingly word association-based segments of “No Time to Think”) “Changing of the Guards” was my number one song on Spotify last year, and I couldn’t even guess what it’s about. I don’t think it matters all that much, though. You get some great lines from these songs, and they sound good, so, whatever.
I think “Street-Legal” is kind of best seen as a more tasteful “Empire Burlesque.” Dylan generally keeps the arrangements down to things he can handle (there aren’t any drum machines or synthesizers to be found), but the catchiness and largeness of sound is there, as it is on “Empire.”
A lot like “New Morning,” too, “Street-Legal” has an exuberance that lends it quality. I wouldn’t say it’s necessarily happy, but it is certainly passionate. Dylan really belts out some of the choruses, something he didn’t really have the ability to do much longer, but at least he uses it for the best here.
In association with its largeness of sound, all of the songs on “Street-Legal” are pretty lengthy, which I think generally works, but each song is maybe a minute or so too long. I really like “No Time to Think,” but there’s no need for it to be over eight minutes long.
I’d be remiss not to mention the best tracks on this record, which include the aforementioned “Changing of the Guards,” the mysterious and incredible build that is “Señor (Tales of Yankee Power),” and the closer, the celebratory “Where Are You Tonight? (Journey Through Dark Heat).” Points are also given for the fact that the best songs are spread evenly across this tracklist.

10. Planet Waves (1974)
Renaissance
A lot of people like to say Dylan’s “Renaissance” or “return to form” or whatever you want to call it begins a little later than “Planet Waves,” so they can start with the real iconic record from that era. I think that’s a little disrespectful to this record, which seems to be constantly overlooked in favor of albums that follow it.
“Planet Waves” is probably best known for “Forever Young,” which actually has both a “Slow” and “Fast” version which play back-to-back midway through this album. (The “Slow Version” is the one you probably know.)
That’s not why I’m such a huge fan of this record, though. Actually, rather than having a single highlight, it’s the sheer consistency in quality, combined with varied moods, that makes me like it so much.
Basically every song on “Planet Waves” has its own “thing” and sounds completely unique, but the instrumentation is uniform enough to tie it all together. It’s a little difficult to explain. If anything, it feels like “New Morning” with more depth and sadness added in, both of which are welcome. Songs like “You Angel You” and “Something There Is About You” would fit right in as some of the better tracks on that album, but there’s also the depressing piano-led “Dirge” and “Going, Going, Gone,” a melancholic ode to finality.
I can’t really even pick out specific highlights, except maybe “Forever Young – Slow Version,” which, again, I’m not even that crazy about, or “You Angel You,” because the strength of this record is so clearly its quality throughout.
If I had one big-picture thought on “Planet Waves,” really, it’s that there’s a clear air of foreboding in odd places. Obviously it’s there in “Dirge,” but it also appears where the lyrics seem to contradict it, like in “Wedding Song” and “Hazel.” I mentioned Dylan’s inclusion of wariness in relation to joy when I was talking about “New Morning;” this is a prime example. Whereas “New Morning” is simple and direct, “Planet Waves” finds itself unendingly confused about how it feels, which is a hard feeling to get across, but Dylan nails it.

Part VI: Great
At this point, we’re not just getting to records that I think deserve some attention, I think they really deserve everyone to listen to them. That’s probably just the fanboy in me again, but I’m gonna get pretty gushy from here on out; I have little bad to say about the coming albums.

9. The Times They Are a-Changin’ (1964)
Folk
“The Times They Are a-Changin’” starts with its iconic title track, so I will, too. It’s an undeniably great song, with every line hitting harder than the last as Dylan pleads for the world to help as the times “a-change.” If Dylan’s early status as the “voice of a generation” were to be distilled into three minutes, this is it.
I also think “The Times They Are a-Changin’” the album colors how you see “The Times They Are a-Changin’” the song. It’s sort of anthemic in a way, despite featuring only Dylan’s vocals, guitar, and harmonica. It projects a hope for the future, that maybe we can all band together and make the world a better place.
I’m not so sure that’s exactly what the song eventually projects. Sure, it’s a plea, but there’s nothing to say that the plea will be answered. Dylan doesn’t promise that the times a-changin’ will be good, merely that they will affect everyone. His prophecies don’t intimate a better future, just a new one. “The battle outside ragin’/Will soon shake your windows and rattle your walls,” he says, offering no comfort, only reality.
I say all this because the often incredibly dark tone of “The Times They Are a-Changin’” suggests that while they’re a-changin,’ it could be for better or, often, for worse.
Some of Dylan’s darkest and most depressing songs are featured on “The Times They Are a-Changin,’” like “Ballad of Hollis Brown” and “North Country Blues,” both of which viscerally illustrate the pains that the march of society inflict upon those within it, and how that march will only continue. “There’s seven people dead on a South Dakota farm/Somewhere in the distance there’s seven new people born,” Dylan sings at the end of “Ballad of Hollis Brown.”
There’s more to be depressed about politically, too. This is hands-down Dylan’s most outwardly political album, where he talks about everything from militarism in America (“With God on Our Side”), societal manipulation through racism (“Only a Pawn in Their Game”), and America’s flawed justice system (“The Lonesome Death of Hattie Carroll”).
Not every song is depressing, to be fair, and some are more personal. “When the Ship Comes In” is a thinly-veiled metaphor that echoes the title track, but has more outward hope, and “One Too Many Mornings” concerns a fading relationship, and both of those songs are highlights.
I think in the end this is one of Dylan’s most immaculate albums, as well as one of his most thematically poignant. It could have ended up higher on this list if not for the fact that, while excellent, it isn’t exactly the most exciting or enjoyable to listen to despite its consistent quality.

8. Time Out of Mind (1997)
Renaissance (Redux)
Jesse Dylan, Bob Dylan’s oldest son, took the cover photo for Tom Waits’ 1992 album “Bone Machine.” And if Dylan ever took after Waits, it’s on his first album after that release. “Time Out of Mind” uses Dylan’s aging and broken voice well for the first time, just as Waits had been doing for years by the time “Bone Machine” came out.
I don’t want to go crazy on the Waits comparisons, though. His connection to Dylan was more of a fun fact that I discovered rather than a concrete connection. The relation clearly shows up at the beginning of “Time Out of Mind,” especially on “Love Sick” and “Dirt Road Blues,” both of which show Dylan weaponizing his voice’s grit, as opposed to avoiding it as he did throughout the 80’s.
Most of the rest of the album, though, shines more because of its stellar songwriting and evocative performance than anything. “Standing in the Doorway,” “Tryin’ to Get to Heaven,” and “Not Dark Yet” are highlights that probably characterize the record best, with spaced-out production backing emotional lyrics and vocals. “Tryin’ to Get to Heaven” also gifts us what is probably the best line from the album, “When you think that you lost everything/You find out you can always lose a little more.”
“TOOM” is a little like “Street-Legal” in its form, with longer songs supporting the feeling of largeness, except the former is more concerned with the space within that size. Whereas “Street-Legal” is large and busy, “Time Out of Mind” is large and desolate, with Dylan’s tiredness lending much to the style.
It’s a little bit of a shame how little Dylan actually came back to this style. While I enjoy his later albums, none of them have this level of immaculate production and bluesy darkness, probably because he produced each album after this himself under the pseudonym “Jack Frost.”
I think in a lot of ways what I like most about “Time Out of Mind” represents. Dylan’s most recent 20 year stretch has been his most consistent, and it all comes back to “Time Out of Mind” setting his career back on track.

7. John Wesley Harding (1967)
What’s This Guy Doing?
You hear Bob Dylan called a poet a lot. “John Wesley Harding” probably exemplifies the poetry of his writing more than any other album.
I don’t want to be misconstrued; I’d say basically all song lyrics are poetry, unless they’re written in prose or something like that. But there’s poetry and there’s poetry, in italics.
“JWH” shows Dylan at his most concise and often his most impenetrably cryptic. The albums preceding this were expansive, with Dylan rambling for minutes upon minutes, using countless vignettes to create vivid and absurd images, but he doesn’t use a line that he doesn’t have to on “John Wesley Harding,” most notably on its most popular song, “All Along the Watchtower,” whose three verses still cause debate today about who the “joker” and “thief” represent, and why they needed to get out of “there.”
The album’s longest track, “The Ballad of Frankie Lee and Judas Priest” is probably the second best song on the album, behind “All Along the Watchtower.” Beyond just being the namesake for the heavy metal band “Judas Priest,” the track is about the dangers of temptation, portrayed through an exchange between the title characters, the latter of whom represents the devil. Dylan does a pretty unorthodox thing, for him at least, at the end of this song by literally outlining its moral. I’m not sure what that means, or if Dylan had just a greater sense of purpose on the track, but it did throw me.
One more odd thing about the album: there’s an abrupt shift before the final two songs on the album. Before, most tracks feature darker narratives and themes, or at least portray a great deal of complexity in their tone, but the final two songs, “Down Along the Cove” and “I’ll Be Your Baby Tonight,” are pretty straightforward sappy love songs. I like both of them, but they do seem oddly out of place.
The biggest downer about “John Wesley Harding” is just how overlooked it is despite its quality. It came after a short hiatus following Dylan’s height of relevance in the mid-60’s, so it generally gets less attention, but it deserves its spot this high on the list.

Part VII: Almost The Best
At this point, we’re getting to some of my favorite albums of all time, period. These albums, as the title indicates, aren’t quite at the top level, but they’re all getting close in their own ways, and I think they all nearly maximize what they are, even if there are some albums with better stuff.

6. Desire (1976)
Renaissance
“Desire” was the big confirmation that Dylan was, truly, back. His album preceding this, which will come up later, announced his re-arrival, but “Desire” assured everyone it wasn’t a flash in the pan.
This record is best known for its opening track, “Hurricane,” about the boxer Rubin Carter, who was wrongfully imprisoned for murder. The song sets a pretty good scene for the rest of the album, which features a lot of long, expansive narrative tracks heavy on Scarlet Rivera’s violin.
Maybe the best of those tracks, and of all the songs on the album, is “Black Diamond Bay,” which tells the story of an exotic resort destroyed by a volcano, introducing several absurd characters, like those characteristic of his work in the mid-60’s. However, on this track and much of the rest of “Desire,” there’s a clearer sense of narrative focus, likely injected by co-writer Jacques Levy.
Levy was a theater director, so he would have more of a sense for more dramatically straightforward writing, which is featured on every song except the two the unendingly vague Dylan wrote alone, “One More Cup of Coffee (Valley Below)” and “Sara,” which are nonetheless great, especially the former. “Isis” is another highlight in the same vein as “Hurricane” and “Black Diamond Bay.”
Another characteristic feature of “Desire” are the frequent soprano vocals of Emmylou Harris, which juxtapose with Dylan’s rasp nicely. Harris sings in duet with Dylan a lot, so at first I thought she was Dylan’s first major collaborator, Joan Baez. Getting Baez to sing would’ve been excellent, especially considering how good she sounded when they played these songs live with the Rolling Thunder Revue, but the fact that Harris could be mistaken for her is a compliment.
There is one gigantic problem with “Desire,” though: “Joey.” We haven’t had an entry into the “Worst Dylan Song” contest in a while; this might be my ultimate pick. It’s an insufferable 11-minute-long opus for a brutal gangster, who by all reports did not deserve redeeming. Dylan does this sometimes; he has a fixation on outlaws, and has a propensity to honor them somewhat inappropriately. He could even be accused of this on “Hurricane,” where he describes Rubin Carter as reserved and not one to incite violence, while Carter had had a history of violence outside the boxing ring, and he himself didn’t dispute that. That didn’t mean he was guilty, but it nonetheless speaks to Dylan’s inability to see those he considered “outlaws” without rose-tinted glasses, and it’s exactly what makes “Joey” so bad. Also, the music is irritating. It’s the only Dylan song I always skip when it comes up on the album.
“Joey” is what took “Desire” out of the top five, to be honest, but it still deserves its place on this list. It’s also grown on me a lot over the past year or so, when I thought it was good, but nothing to especially write home about.

5. The Freewheelin’ Bob Dylan (1963)
Folk
Dylan’s sophomore effort, “The Freewheelin’ Bob Dylan,” sees him diving headfirst into the songwriting that he only dipped his toes into on his self-titled debut, and it’s pretty astounding just how much he hit it out of the park.
“Freewheelin’” lacks the thematic cohesion of “The Times They Are a-Changin,’” but I placed it highest among the folk albums because it makes up for some jaggedness by its relentless personality and some of the best songs ever written.
First, with the negatives, because they are clear: there are some pretty mediocre songs on this album, although nothing is egregiously bad. In fact, a lot are interesting upon first listen, but the wit in songs like “Talkin’ World War III Blues” and “I Shall Be Free” doesn’t really hold up after that, and “Down the Highway” and “Bob Dylan’s Blues” can be downright tedious upon repeated listens to the record.
All of the songs, though even the ones I’m not very fond of, still provide insight and experience with Bob Dylan the songwriter and performer. That’s really the central ethos of “Freewheelin.’” It provides a proper introduction to Dylan himself, and the quirks and charms that come along with his songs. I don’t love “Honey, Just Allow Me One More Chance,” but it provides a look at a looser Dylan, whereas much of the rest of the album is more serious.
The highlights on “Freewheelin’” are all more serious cuts, but they nonetheless vary in style. “Blowin’ in the Wind” and “A Hard Rain’s A-Gonna Fall” are vaguely political and about the state of the world, but seem to be intended to ask more questions than they answer, literally in the former’s case. Still, both of these songs are excellent displays of Dylan’s poetic tendencies and societal awareness, even if they aren’t as specific as Dylan’s later political tracks.
The best two songs on the album, though, are “Girl from the North Country” and “Don’t Think Twice, It’s All Right,” both of which are wistful songs about lost loves, if portraying very separate emotions. The most popular version of “Girl from the North Country” is the one I mentioned earlier while discussing “Nashville Skyline,” a remake as a duet with Johnny Cash. Like I mentioned there, though, the original version on “Freewheelin’” is leagues better. Dylan gives a far, far better vocal performance, and you really feel his pain and regret, plus the cover’s less busy backing doesn’t hold a candle to the 1963 version’s beautiful, tight guitar arpeggios.
Similar arpeggios are present on “Don’t Think Twice, It’s All Right,” so it and “Girl from the North Country” end up sounding rather similar outside of Dylan’s vocals. “Don’t Think Twice, It’s All Right” is rather bitter, unlike its counterpart, and Dylan sells a kind of irritated apathy wonderfully. The song portrays a lot of complex emotions in three-and-a-half minutes, but it all fits.
The biggest debate I had with myself was to put this or “Desire” at number five. I went with “Freewheelin’” partially because of the atrocity that is “Joey,” but I think it also has higher highs, and, importantly, better represents the Dylan that we know, possibly better than any other album he’s come out with.

4. Bringing It All Back Home (1965)
Electric
It speaks to how good “Electric Dylan” was that this is the first of the albums from that era to crop up on the list. It’s even good enough that I considered giving it its own tier, because it was very clearly number four for me.
“Bringing It All Back Home” is Dylan’s first “electric” album, but only half of the songs actually fit that description. The first side is entirely rock songs, while the other is entirely folk.
I like side one less than side two, but it’s still all good and occasionally incredible. “Subterranean Homesick Blues” is one of the best songs ever, as is “Maggie’s Farm.” Both tracks see Dylan going headfirst into rock n’ roll, practically yelling over electric guitars and crashing drums. “Subterranean Homesick Blues” is the purest example of Dylan’s stream-of-consciousness songwriting, too, and “Maggie’s Farm” serves as a metaphor for his relationship with the folk movement, which some thought he betrayed by going rock.
A lot of the rest of side one is similar, with consistent quality but not many other standouts. I like just how loud “Outlaw Blues” is, though, and “On the Road Again” shows some good humor. There are quieter songs, too, which are also great, like “She Belongs to Me” and “Love Minus Zero.”
Side two is where it really gets good, though. The thing that stands out to me most, starting from the first track on this side, is the imagery. “Mr. Tambourine Man” kicks it off, and basically every line sounds like it could have come from a book of poems you’d study in English class. I was going to include a quote, but they were all just entire verses. I’d just listen to the song or read the full lyrics.
“It’s Alright, Ma (I’m Only Bleeding)” is similar, and demonstrates Dylan’s immense talent for rhyme. It was hard to find a quote for this song, too, but I like “Keep it in your mind and not forget/That it is not he or she or them or it/That you belong to.” Dylan’s rapid monotone delivery on this song shows a kind of tiredness, despite the social topics he’s discussing, a shift from his younger self.
“It’s All Over Now, Baby Blue” closes out the album on a melancholic but literal note, and is again a great display of imagery, though nearer “Mr. Tambourine Man” than “It’s Alright, Ma” in sound. It’s unclear, but I think Dylan is saying goodbye to his folk persona as he leaves it behind, with each of his next two albums featuring only one folk song each. It’s a fitting tribute during Dylan’s career transition, asserting that he was on to bigger and better things, even after the greatness he had achieved so far.

Part VIII: Basically Perfect
The title sums this up; these three are essentially flawless, though still distinct. It wasn’t too hard for me to actually rank these, but I nonetheless emphasize that it would be exceedingly difficult for any to be significantly better. They’re all in my top 20ish favorite albums, and number one is my favorite record of all time.

3. Blonde on Blonde (1966)
Electric
It may not be the best Dylan album, but “Blonde on Blonde” is certainly the most Dylan album. I mean that in terms of volume (this is the only double LP Dylan released in his heyday in the 60’s, making it over 20 minutes longer than anything else he released in that period) and style.
If you’re doing a Bob Dylan impression, it’s usually going to be a “Blonde on Blonde” facsimile. Wildly oscillating nasally tones? The best example of those is the title line of “Stuck Inside of Mobile with the Memphis Blues Again,” which is also probably the most Dylan song title there’s ever been. The line, “Everybody must get stoned?” “Rainy Day Women #12 & 35.” Quickly shifting between long, bending notes and rapid talk-singing? That’s “Visions of Johanna.” Aggressively ridiculous passages? See: “Leopard-Skin Pill-Box Hat.”
And it’s pretty obvious why the classic Dylan things come from “Blonde on Blonde:” it’s ridiculously good. Almost every one of the 14 tracks is excellent, with some, like “Visions,” “Memphis Blues Again,” and “Just Like a Woman” being essential Dylan listening.
The album features more of a foray into country rock than Dylan’s previous work, and he substitutes the louder cuts from his past two albums for a smoother sound. “Blonde on Blonde” never gets as bombastic as on songs like “Outlaw Blues” and “Subterranean Homesick Blues” from “Bringing It All Back Home,” but Dylan also has a stronger lyrical focus and the instrumentals make up for their more reserved nature with added complexity. The poetry from side two of “Bringing It All Back Home” is much more present on these rock songs, so it feels like Dylan’s really putting it all together.
“Blonde on Blonde” also has a distinctly more personal lyrical focus than any previous album except maybe “Another Side of Bob Dylan.” “Visions” and “Just Like a Woman” are fully focused on Dylan’s relationships, as are other highlights like “I Want You,” “One of Us Must Know (Sooner or Later),” and “Most Likely You Go Your Way (And I’ll Go Mine).” (Have I mentioned how much Dylan has always loved long song titles, and especially parentheses? It makes writing a breakdown of all of his albums incredibly tedious at times.)
The personal nature of these songs provides a pretty important influence to music in general; in a lot of ways Dylan was the originator of the “confessional” singer-songwriter, and while he had done that before in his folkie years, I think “Blonde on Blonde” was the thing that really brought that persona into the limelight. This, more than his folk records, got widespread listenership. Dylan is often credited for his influence; this is where that most clearly shows.
I find a need to explain why this isn’t number one, because it is to a lot of people. I think, mainly, “Blonde on Blonde” has more filler than anything ranked higher than it, and it’s good filler, but I don’t find myself coming back to “Temporary Like Achilles,” “Obviously Five Believers,” and “Pledging My Time,” as much as I generally enjoy them. 72 minutes is just a lot of time to fill, especially for somebody who released two albums in each of the past two years. Also, “Fourth Time Around” is tedious, and the weakest song on any of these top three records, and “Sad-Eyed Lady of the Lowlands” goes on for a few minutes too long.
I said too many negative things just then. Again, I stress that this is essentially perfect in spite of its minute flaws.

2. Blood on the Tracks (1975)
Renaissance