Greetings, reader!
Well, I just finished a major project - getting acquainted with Bob Dylan's entire discography. Well, his studio albums anyway - I didn't have it in me to shuffle through every live album, compilation and extended play as well. Anyways, as the culmination of Music Month III, here's my ranking of every single one of the 40 studio albums in the beautifully unhinged trajectory of Dylan's career!
40. Infidels (1983)
I know many Dylan fans, especially more apolitical ones, might rank his 22nd studio album significantly higher. The thing is - I can't get past Neighborhood Bully. I know that it was the 80's and that he was probably manipulated into doing the song by studio execs at a fragile time in his life, but still - the message goes so strongly against everything the man was supposed to stand for.
Other than that one song, it'd be an alright record (tracks like Jokerman are good stuff), but the abysmally aged Neighborhood Bully is my least favorite Dylan track by such a long shot that it drags the whole album all the way to last place.
39. Under the Red Sky (1990)
Here' an apt football metaphor for fans of the sport: remember how England had Gerrard, Lampard, Beckham, Rooney, Terry and Cole on the same team and won absolutely fuck-all? That's this album.
Featuring guest musicians ranging from George Harrison and Elton John to Stevie Ray Vaughan and Slash, Dylan's 27th album sounds great on paper but sounds ridiculously underwhelming when you listen to the end product. The tracks are some of Dylan's very least inspired songwriting, and the guest performers aren't utilized for very much. It's a mess, with the quality of songs ranging from fairly ridiculous to fine but forgettable.
38. Saved (1980)
Ah, Bob's born-again era. Yes, that happened!
In the late 70's, the GOAT of never letting 'em know your next move subverted everyone's expectations again, when he very suddenly and randomly converted to Christianity out of the blue and started to make gospel albums. This lasted a few years, and then he un-found God again and went back to secular music. And while finding one's spiritual side can lead to fantastically deep songwriting (see: Ursus Factory's latest album), Dylan's trilogy of Christian albums (and particularly its middle instalment) didn't do that.
I have nothing against the lyrics being religious, but why do they have to be such surface-level plastic? This man was known for making mega-deep songs about any given subject, but when writing about what are supposed to be the very biggest questions out there, he gets all boring and shallow. The arrangements are decent folk-gospel stuff, but I'm still quite merciless to the Christian trilogy's 2nd album in particular, as it doesn't have the "at least this is something new and different" shock value of the 1st or the "hey, some of these songs are pretty good" factor of the 3rd.
37. Down in the Groove (1988)
This aptly named album comes right from the middle of the biggest creative slump in Dylan's career. His 25th album came in a time when he was getting started with the supergroup Traveling Wilburys, and perhaps that's why his solo stuff from the time sounds like he really didn't bother to give a shit. A saving grace that ranks Down in the Groove above the three very worst ones is Dylan's version of traditional classic Shenandoah, which is quite beautiful. Other than that, this record is more bland and uninspired than you'd ever imagine from the dude who came up with Hurricane.
36. World Gone Wrong (1993)
Between the Big Slump and a historical artistic comeback, Dylan recorded two albums of classic folk covers, ditching the rock band for a simple man-and-guitar feel for the first time in a long while. It was a semi-cool move, but the albums aren't anything too special (the latter one in particular).
If you like classic American folk music, you'll enjoy listening to World Gone Wrong, but there's nothing mind-blowing about it - none of the songs could possibly be even close to being the best version of said song out there. I get that the guy (and many of his fans, at that point) yearned for a momentary return to a simple, stripped-down style, but the arrangements here just sound unimaginative.
35. Together Through Life (2009)
As you can surmise from my bottom five being all from the 80's and 90's, most of Dylan's stuff from the current century has been surprisingly solid. His biggest slumps were long behind him by the 2000's, and the man came up with some great stuff in his twilight years. However, the artist's thirty-third studio album is a bit of an exception to the rule.
After an impressive run of albums, Together Through Life can't help but feel like a bit of a dud. The production is decent and the songs sound roughly like you'd expect from the aging folk legend - but there's nothing to really grab onto. All of the songs are alright, but none of them are very special or particularly memorable. A partial reason for this may be that the songs were co-written with Robert Hunter - Dylan is at his best when writing solo (especially lyric-wise), so this collaboration might be why the creative material comes across as very middle-of-the-road.
34. Knocked Out Loaded (1986)
A creative slump could be felt already in the albums leading up to Knocked Out Loaded, but this one is where it really became evident (before reaching a low-point with its follow-up Down in the Groove). Most of the album is underwhelming, veering on downright bad by Dylan standards - but there are a few saving graces that rank Dylan's 24th album ahead his very worst ones.
The cover of Kris Kristofferson's They Killed Him is quite powerful, and the 11-minute Brownsville Girl shows that Dylan still had that magical storytelling touch even when it wasn't evident for the whole album's duration. Those gems make the album a worthwhile listen, but pretty much all of the other tracks do weigh it down more than lift it up.
33. Triplicate (2017)
Here's what's crazy about Dylan's Sinatra era - usually, if an artist made three consecutive albums of Frank Sinatra covers, that would be a defining career move. With Dylan, it's barely a footnote in his chronology (y'know, due to the other thirty-seven albums and various shifts in genre). But yeah - in the 2010's, the man recorded three albums of covers to explore his love for Ol' Blue Eyes - although, by the third one (his 38th album overall), it's not just about Sinatra but rather a larger array of Great American Songbook classics.
Triplicate is the last and the longest out of those albums, and also inevitably the worst - while it is still enjoyable, it does feel like this chapter in Dylan's story had seen its most interesting days and the concept was being milked to the last. It's a guaranteed decent listen for people who liked the previous two records, but a majority of the covers just aren't all that fresh, reading like Dylan had chosen the most interesting covers for Shadows in the Night and Fallen Angels and was now working with left-overs. Some of the covers, like As Time Goes By and Stardust, are still very solid, but overall, listening to the album after the previous two does make one yearn for original material.
32. Shot of Love (1981)
It's Dylan's twenty-first studio album, and the final instalment of his weird-ass born-again trilogy. Shot of Love is far from his best work, but it does score higher marks from me than Saved, for two reasons. Number one, this one goes from being cheesy enough to feel cringe all the way to being so cheesy that it works on an odd, guilty-pleasure way.
And number two - the final track, Every Grain of Sand, is easily the best individual song to hail from Dylan's Christian era. It's a beautiful song, and the lyrics work even in a non-spiritual context - perhaps this is why the absolute madman ended his set with this when I saw him live last year. Absolutely can't imagine any other of the songs from this era being played live by the current, 84-year-old Bob.
31. The Basement Tapes (1975)
I know that most true fans would rank this cult classic a lot higher. The thing is - I know the reasons for his sixteenth studio album being loved by diehard fans, and I feel like I understand them, but the end product still doesn't do as much for me as it does for many. Having this in one's top 15 or even top 10 is a very respectable opinion, but it's not one that I can pretend to have. The album is conceptually cool with its eternity-project bootleg-collection backstory, and I do love the feel of Dylan jamming with The Band.
But, when I'm listening to the album, my enjoyment never surpasses a certain level that it does with most Bob Dylan records. The things that it does well are done even better to my taste on other albums (such as the underrated Planet Waves), and as much as I believe in the power of long albums, this one does feel too long for my taste. It's a vibe, but none of the songs are standouts and the whole thing gets a tad boring at times despite the generally enjoyable roots rock atmosphere.
30. Dylan (1973)
Yeah, there were no pre-1975 albums in my bottom ten. This isn't even because of a stuck-up elitist attitude of old always being better - I recognize a lot of flaws in the artist's early years, and I love a vast majority of his newest stuff. But still, there's something about Dylan's early era that works so magically that even the more flawed albums are a bit better than the flawed albums from later stages in his career. Case in point - his 13th studio album Dylan is very negatively received and has been called his all-time worst record by many fans...and while I see their point, I just have to say that it's not that bad.
Yes, it pales in comparison to the many albums preceding it as well as the one after it. There is plenty to criticize, and its notorious reputation is at least somewhat earned. But still - there's a lot to like as well, and the album, while flawed, certainly isn't a terrible listening experience. Yeah, it's full of covers in a time when the guy was on fire with original material, and many of the covers a tad generic in their arrangements and Dylan's vocal performances. But at its best, Dylan is inescapably decent - the version of Can't Help Falling in Love is a delightful surprise, and The Ballad of Ira Hayes goes hard. This album is definitely over-hated, but still not good enough to be ranked higher than this.
29. Good As I Been to You (1992)
Dylan's twenty-eighth studio album marked a momentary return to simple, bare-bones man-and-guitar folk music in the form of covers of traditional American folk. Good As I Been to You is ranked quite a bit higher than its similar follow-up World Gone Wrong, which can be largely credited to the tradition of Dylan's "hey, let's to something completely different for the next 2-4 albums!" eras starting out strong and then slightly overstaying their welcome.
The albums sound about just as good, but this one feels a bit more fresh. Also, in all its absurdity, Dylan's take on Froggie Went a-Courtin' (known in Finland as children's song Saku Sammakko) was a positively shocking discovery.
28. Slow Train Coming (1979)
You know how I just mentioned that the first album of a certain stage in Bob Dylan's career is often better than its similar follow-ups? Well, that is absolutely why the first album of his born-again trilogy is the best of the three. Say what you will about the singer's bizarrely sudden and short-lived turn to Christianity, but one has to appreciate the sheer "never let them know your next move" boldness when the gospel starts.
Also, the songs on this 19th album of his career are alright - the lyrics aren't as deep as they should be, but the arrangements are a fun clash of folk and gospel traditions. A personal highlight for me is the song Do Right to Me Baby (Do Unto Others), which sounds exactly like you'd expect a suddenly Christian Bob Dylan tune to sound, as you can guess from the objectively hilarious title.
27. Fallen Angels (2016)
This was Bob's thirty-seventh album overall, and the middle instalment of his Sinatra trilogy. In the typical fashion of a certain genre hyperfixation amidst Dylan's career, the second Sinatra record isn't as fresh and exciting as the first, but also not as slightly worn-out as the third - it's nothing mind-blowing, but a good time nonetheless.
None of the covers make for amazing, all-timer arrangements, but they're all on quite a decent level. It's largely what you'd expect from a Shadows in the Night follow-up album.
26. Self Portrait (1970)
Much like 1973's Dylan, the artist's 10th album is one of the most poorly received works from the early stages in his career (man, what a legend of longevity you have to be when your tenth studio album is considered early). And much like Dylan, many have gone as far as to call this his worst album - especially upon its release, and to be fair, it was true back then. Out of the ten first Dylan albums, Self Portrait is clearly the worst. But, he has finished below that bar many times after, so this deservedly polarizing album does make it all the way to 26th place despite its messiness.
I'm generally one to prefer artistic ambition, even when it misses the mark, to anything generic - and maybe that is why I have a bit of a soft spot for Self Portrait despite also being critical of its flaws. The record tries to be something special, and while a lot of it reads as Dylan fighting a bit too hard to subvert expectations by making an album so self-indulgent and convoluted that it would be hard for anyone to really enjoy, there are flashes of genius to be found.
The weird-ass opening track All the Tired Horses is beautiful, and decisions like including a messy live version of Like a Rolling Stone halfway through the album amidst the studio tracks are respectably bold. This album is a lot like David Lynch's Dune - it may be way too messy to really succeed as a work of art, but it's deeply entertaining and I'm glad it exists.
25. Empire Burlesque (1985)
From one "guilty pleasure" album to another, I can't help but like Empire Burlesque. Sure, Dylan's 23rd studio album is a mess of pop, disco, gospel, folk rock and general 80's psychedelia elements that somehow feel simultaneously "man, he's trying way too hard" and "wow, he didn't bother to try even a little" - but inescapably, it's a very fun listen. The song When the Night Comes Falling from the Sky in particular is an experience that you'd never in a million years imagine hearing from Dylan until you do, but one that enriches the tapestry of his music in a gleefully zany fashion.
24. Oh Mercy (1989)
After a streak of many albums that were negatively received, some more deservedly and some less, Bob Dylan surprised everyone (not for the first time, and not the last) with his 26th album Oh Mercy - one that was received on a scale from "momentary return to form" to "absolute comeback". I'm more with the former than the latter - it's a good album, no question about that, but definitely overhyped by some fans and miniscule in scale to the artist's true comeback project from 1997 - but more on that later.
While there isn't as much to strongly like as there are on Dylan's best albums, there certainly isn't anything to hate either. It's all original compositions, the guy is actually doing folk rock instead of dabbling in a totally new genre and/or religious devotion for once, the production is decent, and Dylan's voice sounds great (it's right in the sweet spot between the idealistic nuances of Young Bob's singing voice and the raspy, gravely tone of Aging Bob). None of the songs are masterpieces, but ones like Political World and Ring Them Bells are really good.
23. New Morning (1970)
I recognize that it's pretty ridiculous how barely New Morning is ahead of Self Portrait - they came out in the same year, and one is (if I dare say such a word when comparing art) objectively better than the other. Most Dylanites would probably have the better 1970 album about 20 spots ahead of the other one, but with me, it's just a matter of three spots. In my defense - as I established, I like Self Portrait more than most fans do and consider it overhated, and this small margin is definitely more about that than about me having anything against New Morning. This album rocks.
Dylan was still in his country era (yes, that happened), but not quite as passionate about it as he was with the full-yee-haw vibe of Nashville Skyline. Dylan's 11th album is light and enjoyable, and it really sounds like the artist is having fun for once and not concerned with subverting expectations and diving into a totally new genre each week. My favorite song from this chill record has always been Winterlude, which is just adorable in its quirky and unserious nature. It's pretty awesome that the same dude who wrote the lyrics to The Times They Are a-Changin' also wrote the line "Winterlude, this dude thinks you're fine!".
22. "Love and Theft" (2001)
One of my favorite niche archetypes for an album in an artist's discography is the post-comeback album. Much like Iron Maiden's Dance of Death after Brave New World or Springsteen's Magic after The Rising, Dylan's thirty-first album comes at the heels of a big comeback album, and largely manages to ride its high. Just like its counterparts from other artists with similar trajectories, "Love and Theft" isn't as good as its predecessor, but comes somewhat close due to being similar enough in a good way. Dylan had momentum, and capitalized on it with style.
Much like Oh Mercy, this album is a solid whole, where none of the songs pop out as all-timers, but they all keep at an impressive level with none of them dragging the end product down. The production, by Dylan himself under pseudonym Jack Frost, is pretty amazing, as the album sounds neat and atmospheric in a way fitting this phase of his career.
21. Street-Legal (1978)
Now, this phrase could be said about any number of Bob Dylan albums, but I'd argue that it fits his eighteenth one better than any other - this was the last album to drop before things got weird.
For 70's Dylan, Street-Legal is largely what you'd expect - the backup band is a bit larger and the genre is less folk-y and more straight-up rock, but you can definitely hear faint traces of 60's Dylan and strong echoes of 70's records like Blood on the Tracks and Desire here. After this album, Dylan would convert to Christianity and make three albums in a row about praising the Lord, and things would only get weirder from there with the mixed messages of Infidels and the psychedelia of Empire Burlesque. In the context of Dylan's chronology, Street-Legal feels like a nice day you spend with your old friend before everything in your life turns upside down, so it's an easy album to fondly look back on.
20. Tempest (2012)
Dylan's thirty-fifth studio album was his last feat of original songwriting for a while, as he followed up on Tempest by doing his whole Sinatra-cover escapade. Following the much-better-than-expected trend of his albums throughout the 2000's, Tempest was once again a delightful surprise - the guy quite simply still got the chops.
Like most of his critically acclaimed albums of original music from that era, Tempest simultaneously does and doesn't feel like Bob Dylan. It's almost unrecognizable from the style of his most classic works in the 60's, yet if you've listened to his whole lexicon from there to here, the sound and style make all the sense in the world as a natural next step in how his songwriting and performing had evolved over the decades. Points especially for the 14-minute title track - hearing Bob Dylan riff about Titanic (not the ship, mind you, but specifically the 1997 movie) is all sorts of weird, but oh man, it works wonders.
19. Bob Dylan (1962)
Dylan's debut album is a hard one to rank for all sorts of reasons. One might argue it to be a lot lower, as it's mostly covers of traditional American folk standards with only two original songs, and the 20-year-old musician was understandably still finding his voice and on his way to becoming the icon we know and love. But, on the other hand, it could be argued to rank much higher, as it's a crucially important first step, and signs of the greatness to come can be heard in an almost spooky way.
While you can hear that the young songwriter was still in the midst of a learning curve, there are some prominent flashes of genius - the original track Song to Woody has the makings of a folk classic, and some of the covers (House of the Risin' Sun, Freight Train Blues) really bring out the kind of expressive singing that he would really learn to capitalize on with later records. The album sounds like there's still a long way to go for this guy to become the Bob Dylan, but at the same time, it's already so good that it ultimately makes sense that the very next two albums would thrust him into greatness and etch themselves in music history.
18. Shadows in the Night (2015)
I have an almost indefensible amount of love for the opening instalment of Dylan's Sinatra trilogy. Generally, I almost always prefer his original works to his cover albums, but there are a few key exceptions. Suddenly deciding to do a fuck-bunch of Sinatra covers is such a fascinating career move, and the first of these albums in particular works so well. The style of the arrangements walks such a fine line - there's just enough traces of Sinatra's own swing-groove to make the songs feel like proper tributes, but there's so much of Dylan's own touch that they're definitely compelling as covers.
Many of the songs escalate into a free-tempo void, with the text getting room to breathe while Dylan's aging voice is as expressive as ever and interprets with reflection and heart. Classics like I'm a Fool to Want You and Autumn Leaves get atmospheric interpretations, and the underrated What'll I Do is the sentimental highlight.
17. Modern Times (2006)
The impressive string of critically acclaimed albums in a late stage in Dylan's career, starting off with Time Out of Mind and "Love and Theft", just kept going in a relentless fashion with his 32nd studio album Modern Times. It's a classic case of "If it ain't broke, don't fix it", with the tried-and-true sound of the preceding records and Dylan's producing (as Jack Frost) working like a charm once again.
The only distinctive difference in style to the two previous records is that Modern Times veers more strongly into Americana territory, with influences of Mexican music being a more prominent additional spice in the melting pot of rockabilly, folk rock and blues. This makes for a truly vibrant atmosphere, felt deeply in tracks like Thunder on the Mountain and Spirit on the Water. Excellent stuff.
16. Christmas in the Heart (2009)
I know - objectively, this is way too high a ranking for Bob Dylan's Christmas album. But, the thing is - trying to compare music objectively is A) dumb, B) pointless, C) soulless and D) just really, really f**king dumb. Comparing music subjectively, on the other hand, is a brilliant means of analyzing one's own opinions and relationship to music, and fun as hell! And subjectively, I'd be lying to myself if I ranked Christmas in the Heart any lower.
Bob Dylan's relationship to audience expectations is much like the One Ring's relationship to its bearers in The Lord of the Rings - if things have been similar for too long, the Ring (or the Bob) grows tired of complacency, and makes something happen to cause a new chain of chaos. Leading up to 2009, Dylan had made three critically acclaimed albums, roughly similar to each other, in a row - and as fate would have it, something had to change. This guy is all about never letting them know their next move, and now his fans had gotten complacent. Luckily, the Bob has a will of its own.
I doubt that anyone had "a BOB DYLAN CHRISTMAS ALBUM" on their 2009 bingo cards - he feels like such an unlikely artist for such a project. Then again, defying expectations and challenging his fans is the man's whole thing, so I find the choice very fitting. Furthermore - I don't care how much some people hate the end product, I absolutely love it. I'm guessing that only a small minority falls into the "both circles" section of the venn diagram for fans of Christmas music and fans of Bob Dylan (another reason why this was an insane project creatively), but I certainly do. Listening to this album and reading about its negative reception, I feel like Joey from F.R.I.E.N.D.S. - "I mean, what's not to like? Bob Dylan, good. Christmas music? Good. Chaotic arrangements? GOOD".
Dylan's versions of beloved classics like Winter Wonderland and O Come All Ye Faithful may not be their all-time best versions, but they're not bad either. Some of the arrangements take a more relaxed tone just like you'd expect from an aging folk icon, like Hark the Herald Angels Sing, but with others, he has SO MUCH FUN. A definitive highlight for me is Must Be Santa, and particularly the part where he sings "Come Dasher, Dancer, Prancer, Vixen, Eisenhower, Kennedy, Johnson, Nixon, Dasher, Dancer, Prancer, Vixen, Carter, Reagan, Bush and Clinton". That moment is exactly what one imagines when hearing that a Bob Dylan Christmas album exists, in the best way possible.
15. Shadow Kingdom (2023)
At this point in his career, Dylan had spaced out his original material by doing cover albums of classic folk tunes, cover albums of yuletide classics and even cover albums of the Sinatra era - but there was one surprise career move left in him. For his fourtieth album - possibly his last one - the 82-year-old folk legend turned to cover the songs of a truly fabled and mythical artist...Bob Dylan.
Now, many artists have released new versions of their older songs, and it's not always something special...but oh boy, Shadow Kingdom hits different. First of all, Dylan's voice sounds largely like it did when I saw him live last year except much better thanks to the production - namely, he truly sounds like an old man near the end of his road, as you can hear traces of his trademark sound from his golden days in his delivery yet you can also feel the toll the decades have taken on him. Dylan's singing has always been deeply expressive, but here it is arguably more so than ever before - with every syllable, he's articularing some strong aim and meaning, conveying so much nuance and emotion.
And the arrangements - oh man, what a treat. The songs he chose to re-do aren't his biggest hits, but they aren't totally obscure either - it's a collection of songs that fans enjoy, some being the bigger hits from overall lesser-known albums while others are among the more forgotten tracks from his big albums. Here, he plays them much like they've been played live in the past decade - a slow, transcendental touch, giving each number room to breathe, while each song transitions into the next one in a borderline magical way.
The songs are so atmospheric that in many cases (I'll Be Your Baby Tonight, It's All Over Now Baby Blue) I actually prefer the Shadow Kingdom version to the original. And even with the ones where the original is inevitably more sacred (Tombstone Blues, Queen Jane Approximately), the Shadow Kingdom version is a fascinating addition. The tracks here don't feel like mere covers, but rather convey a feeling that Dylan's songs are living, breathing things that have evolved and adapted over the years, and aged in a gripping yet graceful fashion along with the man himself. Haunting stuff.
14. John Wesley Harding (1967)
Pretty much only an artist like Bob Dylan could have an album this good that still doesn't make it to the top ten, and isn't even all that close. The man's eighth studio album marked an important transition, as he started to mix in elements of country rock into the folky roots rock stuff from the previous few albums, making for a sound that builds a bridge into the full-fledged country era of the few albums that came after this one. John Wesley Harding isn't quite full-on country yet, but the direction is so palpable that it gives crucial context (Nashville Skyline would've sounded totally out of the blue without having this album paving the way).
The highpoint here is All Along the Watchtower - while Hendrix's cover is even better, that doesn't take too much away from how much ass the original kicks as well. Tracks like I'll Be Your Baby Tonight and the titular John Wesley Harding rule as well, and there's not a bad or even subpar track to be found.
13. Another Side of Bob Dylan (1964)
Dylan's fourth studio album finishes the first of many trilogies in his discography - albums #2 through #4 were acoustic folk records, full of original compositions and socially charged lyrics in the vein of the civil rights movement. After this one, he'd do the first of many surprise pivots, changing up both the genre (adding electric instruments and going all rock 'n' roll) and the themes (the poor guy got overwhelmed of his status as the "voice of a generation" and abandoned the protest songs for a while).
Another Side of Bob Dylan isn't nearly as good as the two absolute classics that it follows, largely due to the lack of masterpiece songs. There aren't any bad tracks, and most of the songs are just as good as the more average songs on The Freewheelin' Bob Dylan and The Times They Are a-Changin', while being very similar thematically and production-wise as well - but there are no 10/10 tracks, which sets this one apart from its predecessor.
If you love the previous albums, you'll definitely enjoy listening to this one, but after the amount of all-timers that the guy wrote for those records, it's almost weird how the songs on this one never reach past that certain level. Still, the overall level and style here are awesome enough to carry the album all the way to 13th place.
12. Rough and Rowdy Ways (2020)
This was Dylan's thirty-ninth album - meaning that it's his second-newest one, and possibly the last-ever album of original music we'll ever get from him. It's unreal how a guy who had made hundreds of original songs, across six decades, could still have it in him to write such fresh and interesting new tunes after that, but the man sure defied expectations here. His voice may sound old and grainy, but his lyrics and compositions don't sound one bit tired. They read like a true artist doing what he has always done - putting new music out there, writing honestly what is currently on his mind, and it's basically as great as ever.
The album opens with I Contain Multitudes, which always makes me choke up - that text, delivered by the 79-year-old's aging voice, always feels like he's reflecting on his whole career and slowly starting to bid farewell (don't get me started on how emotional I got when he performed it live in Helsinki last year). The rest of the album's A-side is a collection of decent tracks, with hardly any of them popping out amidst the rest, but every one plays an important part for keeping up the atmospheric momentum.
The real treasure here is the B-side, consisting entirely of one 16-minute behemoth: Murder Most Foul. The lyrics, detailing the JFK assassination to a full extent by musing on the world that paved the way for Kennedy, the world that he tried to build, and the world that was shaped by the aftermath of that day, are as good as anything Dylan ever wrote in his golden years. What a masterclass.
11. Pat Garrett & Billy the Kid (1973)
Yeah, I love Dylan's obscure twelfth album to an admittedly weird degree. While this soundtrack album to the western film of the same name does count as a studio album, it is obviously an exceptional case. Dylan acted in the movie as well, and was asked to compose the soundtrack. Now, I have to admit that I haven't even seen the film - but I still absolutely love the soundtrack album. Most of the tracks are instrumental, and could be accused of being generic western stuff - but I love the vibe that Dylan's touch as a composer brings to them. It's a deeply vibrant listening experience with a mood of its own.
And, of course, the album and movie alike are remembered best for one song, one that gained a legacy that far surpasses its place of origin - Knockin' on Heaven's Door. Say what you will about the Guns N' Roses cover being arguably even better, the original is still a moving masterwork, and it works so well in the context of the album. But, as much as I love the song, I don't agree with the general assessment that the song carries an otherwise mediocre album - sure, that track is the highlight, but everything around it is pretty damn beautiful as well.
10. Planet Waves (1974)
What a total f**king jam! Most Dylan fans would rank his fourteenth album lower - the general consensus seems to be that the record is liked but not loved, so probably between places #20 and #30 for a lot of folks. I, however, consider Planet Waves to be hellishly underrated - for whatever reason, I get a similar enjoyment out of this one that most fans seem to get from the arguably overrated Basement Tapes.
Dylan is supported by his fabled companions The Band here, and honestly, their collaboration is at its very best. Sure, it's not the very best album for Dylan as a lyricist or a composer, but as an arranger and performer, I'd argue that this one is in the very highest tier. It's a deliciously fun listening experience, as Dylan jams it out with The Band in a true roots rock fashion.
The most praised part of this record is the two back-to-back versions of the song Forever Young, and while that dynamic duo deserves all its acclaim, the personal highlight for me is the closing track Wedding Song. It's probably the most genuinely beautiful love song that Dylan did (out of the happy ones, that is), and such a great song for its context that I decided a while ago that listening to that, out of all the songs in the world, will be the first thing I do after waking up when my own wedding day arrives.
9. Time Out of Mind (1997)
Here we have one of the great comeback albums of all time. After two decades of spiraling from sudden Christianity, through 80's psychedelia and a creative rut all the way to low-effort cover albums, Dylan sat down to make his thirtieth studio album - and the guy f**king cooked. Daniel Lanois' work as producer fits like a glove for Dylan's songwriting and arrangement inspiration at the time - and what a flow of inspiration that was.
Every track is pretty much flawless, and the collection makes for a thematic whole just as great as its individual parts. When listening through Dylan's discography chronologically, the first moments of the opening track Love Sick make for a magnificent payoff - you can immediately hear how Dylan was using more effort, and tapping into more creativity, than he had for a long, long time. I must also give credit to the track list - as a huge setlist nerd, I consider this album to have one of the all-time greatest song orders. For nearly the whole album, every other song is a subdued ballad existing in an almost tempo-less void, and every other one is a slow-grooving rockabilly / roots rock jam that sounds like the Bob Dylan we knew and loved from the 60's has matured in a graceful manner.
It's hard to choose any individual tracks to praise over any others, as it's all so amazing - but two that deserve special shout-outs are Make You Feel My Love and Highlands. The former became one of the very rare songs to reach the status of a 'standard' in the 21st century, largely because it's such a beautifully melodic masterpiece, while the latter is one of the great closing tracks across Dylan's career, as he muses some grade-A lyrics across an atmospheric arrangement for sixteen minutes.
Time Out of Mind won three Grammys - Album of the year, Best contemporary folk album and Best male rock vocal performance. Very deserved.
8. Blonde on Blonde (1966)
Many Dylan fans, especially ones so deep in the rabbit hole that they consider his "big three" iconic albums to be a tad overrated, seem to put Blonde on Blonde in their top two as a rule of thumb. And I get it - the man's seventh studio album is an excellent production, with no bad or even mediocre tracks, with the lyrics being among Dylan's best work while the arrangements make the listening experience into a solid whole. I just have a large handful of his albums that I enjoy even more.
But, yeah - Blonde on Blonde does everything it's supposed to do and does it well, with the lyrics especially being top notch work on most of the tracks. You'd have to listen to a vast majority of Dylan's discography to fully understand why he became the first and only person to win the literature Nobel for songwriting, but if you had to listen to just one album to get a bit of an idea, you couldn't do much better than this one. The interpretational musings of Visions of Johanna, the poetic bars of Most Likely You'll Go Your Way and I'll Go Mine, the descriptive storytelling in Sad Eyed Lady of the Lowlands...ah, that's the stuff.
7. Nashville Skyline (1969)
Yee-haw! I don't care how unserious this album sounded in the time of its release to folk elitists and country purists alike, I will die on the hill that the Bob Dylan country album is a heck of a good time. Sure, Dylan's style of crooning makes him sound like Kermit the Frog, but so what? This fresh jolt of country-western tunes opens with a version of Girl from the North Country featuring Johnny Cash as Dylan's duo partner, and this is followed by the instrumental jam Nashville Skyline Rag - and this has got to be one of the greatest two-song opening numbers in popular music history.
The rest of the album keeps up the good work, with good-time tunes like To Be Alone with You and Country Pie. But yeah, those two opening tracks pretty much guarantee a top 10 spot for this weird and fantastic record.
6. Bringing It All Back Home (1965)
You can claim quite a few Dylan albums to have changed the trajectory of modern music history, but his fifth one in particular deserves such a statement. While it doesn't quite have the household name -type of popular acclaim that his most successful albums do, it is basically just as good music-wise, and arguably even more influential than its more famous counterparts.
The A-side is marked by the first time that Dylan went electric with a full band to back him up - this was seen as a controversial move especially by folk gatekeepers at the time, but it seems that with the passage of time, more and more people have landed in agreement that this was a good thing. Especially as that A-side features total bangers like Maggie's Farm and Subterranean Homesick Blues.
The B-side is acoustic folk more in the vein of the previous few albums, making the album read like a transition between the Freewheelin' era and the Highway 61 era. The songs in this second half may be less groundbreaking arrangement-wise, but every bit as good musically - Mr. Tambourine Man and It's All Over Now, Baby Blue are massive fan favorites for a reason.
5. Blood on the Tracks (1975)
Dylan's fifteenth studio album may be the only one to gain even more appreciation from the niche fans (the type to say "The Times They Are a-Changin' is overrated" and "I've listened to Dylan's entire discography fifty times") than Blonde on Blonde. And I get it - while I feel firm about ranking Blood on the Tracks fifth, I do have a sneaking feeling that it might go a spot or two upwards if I listened to all these albums again, and again. Regardless of that, it's hard to argue that this artistic masterwork wouldn't be a top five album for Dylan.
The production is so cohesive that the listening experience feels almost boring when compared to the chaos of Dylan's previous 70's records - until you realize that what you're hearing is the artistic vision of a truly locked-in artist being interpreted in a raw, genuine manner. This is the closest Dylan ever came to making a concept album - it almost feels wrong to listen to any of the songs individually on a playlist, as they all come into their own so much stronger when put into the context of the album. The instrumentation and Bob's voice sound great, the lyrics are absolutely brilliant, emotionally honest ramblings of a recently divorced man, and the whole thing is just such a masterclass.
4. Desire (1976)
Oh, hell yeah. For his seventeenth album, Dylan remained locked in post-Blood on the Tracks, and I will die on the hill that the slightly less acclaimed (but still really f**king acclaimed) follow-up is even better. The man's lyrical wizardry is on full display, from the return-to-form protest song Hurricane and the emotionally raw honesty of Sara to the vibrant, mystical storytelling of One More Cup of Coffee and Mozambique. The americana-vibe in the arrangements is exciting, and Dylan's singing style finds a whole new level of good-weird with his odd nuances and inflections.
3. Highway 61 Revisited (1965)
Yeah, this is the stuff. This deservedly mega-acclaimed album opens with one of the greatest intros in all of rock music, with every little detail from Bobby Gregg's simple yet effective drum fill to Al Kooper's addictive organ sound being as iconic as it gets. Once Dylan's energetic vocals kick in, the listener is confronted with an inevitable fact - Like a Rolling Stone, while not even being the greatest overall song in Dylan's catalogue, has got to be one of the greatest rock tracks ever recorded.
Yet the quality doesn't really diminish much at all after that! Even the least-good songs on Highway 61 Revisited are quite flawless and simply less memorable than its best tracks, and oh boy, don't get me started on those highlights. The relentlessly hectic energy of Tombstone Blues, the brilliant chords in Queen Jane Approximately, the deeply emotional and melodic vocal expression in Ballad of a Thin Man, the rock 'n' roll fun of the title track...oh man. The album ends with the reflective 11-minute track Desolation Row, which was probably the most famous song in the largely obscure setlist when I saw Dylan live - and sweet Jesus, what a harrowing experience that was.
Dylan's sixth studio album completed his transition from acoustic folk into electric rock territory, and as much as it split opinions back in the day, it has very much become the consensus that this album changed the course of popular music in a good way, and remains one of the best albums in rock history.
2. The Times They Are a-Changin' (1964)
Now this is the stuff. As much as I'm all for Dylan's shift in genre to rock (and then to country, and then back to folk, and then gospel, and then whatever the hell Empire Burlesque was, et cetera), it is hard - impossible in fact - to beat the height of his OG folk days. Mind you, I don't want to take anything away from his later changes in course - I'm positive that albums like Highway 61 Revisited and Nashville Skyline are a lot better than his sixth and ninth albums would've been if he had kept doing similar acoustic folk and trying to re-capture the glory of The Times They Are a-Changin'. But, as cool as those fresh directions were, they can't quite surpass this one.
Dylan's third studio album comes from the height of his status as the "voice of a generation". While the man himself grew tired of that role, it cannot be disputed that he earned that title with his timely lyrics. America was at a crossroads, with the civil rights movement gaining traction while the powers that be did their everything to keep their status quo - and suddenly there's this weird little guy, with terrible posture and an odd singing voice, writing songs that capture the moment with perfection.
Of course, Dylan wasn't alone - the civil rights era was marked by many great musicians using their platforms for good in a way that really puts the cowards we have topping the charts today to shame. By the time that Dylan refused to be the megaphone for the moment and temporarily shifted to less political music, it wasn't a big loss, because by then, America had Joan Baez, Sam Cooke and Aretha Franklin to look up to. But in early 1963, when protest songs weren't a commonplace item, this album played a massive part in igniting a fire that would speak to a generation and remain quite timeless for the generations to come.
The compositions and arrangements are decent acoustic folk music - but it's the lyrics, by the greatest lyricist to ever live in his prime, that make this into one of the all-time great albums. The Ballad of Hollis Brown is one of the most heartrbeaking stories ever told via song, while With God on Our Side uses dramatic irony to make a damning statement about atrocities committed in the name of religion, and Only a Pawn in Their Game remains relevant with its poetic analyses of how evil institutions radicalize regular people for their cause. And then there's the title track - one of the most important songs ever written. Whether I'm watching footage of the 1964 Newport Folk Festival, watching that one episode of The West Wing or channelling my inner Dylan in karaoke, this song always hits hard with its pitch-perfect text that remains as poignant today as it did on the day of its release.
1. The Freewheelin' Bob Dylan (1963)
Okay, okay - *THIS* is the stuff. One of the strangest shifts in Dylan's career trajectory is not a shift in genre at all, but a shift in quality - his first album is decent but clearly still an artist in his training wheels, and then his second album is one of the greatest albums ever made. That's a pretty f**king huge step right there.
Most Dylan fans seem to appreciate many of his slightly later works even more - while they all have an obvious appreciation for this classic, most rankings do seem to put either Blonde on Blonde or Blood on the Tracks ahead of his second and third albums. But that could never be me - the Bob Dylan whose music I fell in love with was the young dude armed with an acoustic guitar and a harmonica, writing protest songs with philosophical and idealistic lyrics, and nothing will ever beat the unique atmosphere and emotional attachment to the lyrics that I get from The Freewheelin' Bob Dylan and The Times They Are a-Changin'.
The big question for me was how to rank my obvious top two, and I think that my eventual decision is similar to why I prefer Metallica's Ride the Lightning over Master of Puppets. With some artists, the third album becomes an ultimate fan favorite as it further perfects the style of the second, but there's some rawness to the unfinished yet genius style of the 2nd that becomes unbeatable for a fan like me.
This might be the only album ever made where the end product would be basically just as good if you removed any song, no matter which song. Even the biggest classics have to somewhat rely on their best tracks - Abbey Road without Come Together or Appetite for Destruction without Welcome to the Jungle immediately lose quite a chunk of their power. But with this one, the collection of songs is so insanely high-quality that I might honestly rank it as my #1 favorite Dylan record even if you removed Blowin' in the Wind. It would still be the album full of masterpieces, from the beautiful atmosphere of Girl from the North Country and the deeply resonating Don't Think Twice, It's Alright to the earth-scorching lyrics of Masters of War and Dylan's skills as a composer catching up to his genius as a lyricist for A Hard Rain's a-Gonna Fall.
It's absolutely insane that all these songs are on the same record, especially when considering that they were written and recorded by a 21-year-old who nobody had heard about back then. For contexts like going on a walk on a rainy November day or sitting on an evening train with a tired mind, there is no better album in the world than this moody and melancholic yet profoundly hopeful masterwork. As much as I appreciate the different roads that Dylan's musicianship would go on to travel throughout his career, nothing he (or anyone) ever did could quite match up to this ultimate lightning-in-a-bottle product of pure genius.
Thank you for reading! Music Month III is now over, so tune in next week as I return to my usual movie/TV topics with a ranking of my top 10 favorite episodes from Orange is the New Black.
