
There’s Bob Dylan, Shakespeare and Michelangelo as far as many Western art fans are concerned. And, making my job of ranking the songwriter’s albums is the fact that he’s produced more material than his William and Mickey combined.
But Dylan’s work is a delight. He is possibly the premier songwriter. And one of the reasons for it is that he has never stopped to work on his skills and to add to his repertoire.
I love Dylan’s songs. I think that he is one of the greatest rock artists of all time. Yet, yes, cynically, I am posting this ranking in time for the release of another Bob Dylan bio, “A Complete Unknown.” Writers have done worse things.
Ok. Ok. I have not included the glorious Bootleg Series, many (but not all of) the live albums, compilations or The Travelling Wilburrys. I broke my own rules a couple of times, as you’ll see, but the notoriety of the records made it necessary to have them included.

Bob Dylan’s Discography Ranked

“Dylan” (1973)
If Dylan’s self-portrait left some fans wondering what the artist meant by it, “Dylan” clearly was assembled by the child of a record label exec. Unsanctioned and, famously, a money grab, this is a collection of odds-and-ends recordings meant to punish the songwriter for fraternizing with David Geffen’s Asylum Records.

“Shadow Kingdom” (2023)
There are numerous hardcore Bob Dylan fans who have heard all the records and seen him play live numerous times but who cannot identify the songs he plays live. “Oh, is that “Like a Rolling Stone.”
Fascinating and baffling, Dylan has kept his interest in the “Never-Ending Tour” through the years by changing the arrangement of the songs continuously.
Most of the tunes on “Shadow Kingdom” were originally released on the famous 60s and 70s Dylan albums. But they’re given a completely new coat of paint here. The new arrangements lend themselves to a dreamy, otherworldly experience, sure. But you may still be finding yourself looking at the credits to find out what to what you’re listening.

“Self Portrait” (1970)
Bob Dylan was so beloved and so sick of adoration that he sometimes challenged the fan’s patience. “Self Portrait” is to Bob Dylan what “Metal Machine Music” is to Lou Reed’s discography, albeit less intrusive-sounding.
“All the Tired Horses” is just gorgeous. And you’ll be surprised to hear Dylan covering rivals Paul Simon and Gordon Lightfoot.
But, very often, you’ll find yourself wondering if Dylan has hired a stand-in who barely can imitate him. It’s a baffling release, more of a practical joke than an album.

“Under the Red Sky” (1990)
One of the great things about Bob Dylan is that, I’d assume, he never reads his reviews. He is relaxed about recording new material, whether he turns in classics or laidback, light affairs.
“Under the Red Sky” is the latter, an album where the great man doesn’t feel like trying too hard. That could’ve been alright as there are plenty of hired hands on decks willing to improve the record. Dan Was produces. And everyone from Elton John to Slash, Stevie Ray Vaughan or Bruce Hornsby make an appearance.
But the songs aren’t really there. Dylan doesn’t sound fully committed. “Under the Red Sky” doesn’t make much of an impression.

“Saved” (1980)
On “Saved,” Dylan jumped head-first into newborn Christianity. He’d hinted at his interest in “Slow Train Coming,” of course.
And while a happy, content Dylan usually produces excellent material, sadly, his Christian albums aren’t very entertaining.
In fact, this period is slightly baffling to fans and casual observers. To his credit, however, Dylan doubled down, refused criticism and made more of these records.

“Shot of Love” (1981)
A new Dylan record has never been a predictable affair. “Shot of Love” is another Christian album. But most of it, all the way down to the artwork, isn’t very interesting.
This, for me, was a surprise. This is, after all, the man who had written “All Along the Watchtower” and a number of other songs that drew inspiration from the Bible.
But “Shot of Love” is better than “Saved.” It’s a bit more robust in places. And Dylan is willing to bring out more of his humour to the affair.
“Lenny Bruce” is good, and Dylan’s interest in stand-up comedy is an amusing detail.
And, “The Groom’s Still Waiting at the Altar” is one of my absolute favourite songs of his. The lyrics may be inspired by his Christian faith, but they have a real bite. This could’ve easily found room on “Highway 61 Revisited.” If only Christian Dylan had more of these songs.

“Knocked Out Loaded” (1986)
Fans, Christian or not, drew a sigh of relief when Bob Dylan announced that he would release “Knocked Out Loaded.” Why? This is a non-secular album. It comes on the heels of the pretty convincing “Empire Burlersque.” And it sees Dylan pick a wide array of collaborators including Tom Petty.
But the one great song song on this is “Brownsville Girl.” That one is remarkable, but the rest of “Knocked Out Loaded” is less so.

“Christmas in the Heart” (2009)
Literally, when Bob Dylan smiles in concert, this makes the news. What a joy it must’ve been then for fans when he announced an earnest Christmas album. The man is enjoying himself!
Of course, the irony is that there is not a single non-Dylan fan who would like to hear him croon the classics. Regardless, if you’re a convert, this version of “Here Comes Santa Claus” will be a real delight.

“Down in the Groove” (1988)
By the 1980s, Dylan was trying out different backing bands on each record and trying out different life philosophies. What hurts “Down in the Groove” is that this time it doesn’t sound like he’s trying hard enough.
The sound of the record isn’t too exciting. But I think that some of the songs on here are great. “Death is Not the End,” “Let’s Stick Together,” or the Grateful Dead-inspired “Silvio,” are all real gems.

“Slow Train Coming” (1979)
“Slow Train Coming” was viewed as a return to form upon its release. But it was also a surprise that Dylan embraced Christianity as a religion and inspired songs that dominated talk around the album.
“Gotta Serve Somebody” is fine. It became a hit. John Lennon parodied this in the studio. And Dylan’s heart is certainly in this.
While the material is not bad, I admit to never liking this. It was the first full Bob Dylan album that I owned. It bore me so much that I didn’t try again for a few years. But don’t let my personal experience keep you away. You can do much worse than “Slow Train Coming.”

“Good as I Been to You” (1992)
Your enjoyment of “Good as I Been to You” of your love of classic folk music. For some it’s a record on which Dylan treaded water. For others, it’s Dylan returning to his roots and digging up great, traditional folk numbers.
Hearing 90s Dylan sing behind an acoustic guitar and harmonica once more is noteworthy enough. This likely, ultimately, led to the “MTV Unplugged” concert.

“Shadows in the Night” (2015)
Fans were happy to learn that Bob Dylan was a Frank Sinatra fan. So little is actually known of one of the most famous musicians in the world.
But few expected Dylan to deliver a cover album of Sinatra tunes. It does make sense, though. Both men possess highly distinctive tones and famously debatable vocal abilities.
“Shadows in the Night” is a commitment to old-time music and a really enjoyable affair. It would rank higher on the list were it not to the numerous and important albums of original material.

“Shadows in the Night” (2015)
“Fallen Angels” was the companion piece to “Shadows in the Night.” It was recorded at the same time. It also features songs made famous by Frank Sinatra.
It ranks higher on the list simply because this is devised as a happier, lighter affair. And, I think that Dylan sounds best when he is enjoying himself.

“Triplicate” (2017)
“Tempest” was a trilogy of discs that ended a trilogy of albums in which Dylan not merely dipped his toe but swam deep into the ocean of classic songs.
It’s the fact that Dylan has written plenty of classics himself that makes it all the more interesting. “Tempest” might just be the best of the bunch, simply because of the relaxed delivery. Here, at times, Dylan almost sings the tunes as if they’re his own. And that, for me, what a treat.

“Pat Garrett & Billy the Kid” (1973)
“Pat Garrett & Billy the Kid” is a soundtrack album for a great movie. As it turns out, Dylan was a good actor. As it also turns out, working with like-minded people, like director Sam Peckinpah, brought out the best in him.
The album contains the immortal “Knockin’ On Heaven’s Door.” It’s one of the most covered songs for a reason. Just ask Axl Rose!
The rest of the album is a little unpolished and best works when paired with the movie. Still, songs like “Billy 1” rather good.

“World Gone Wrong” (1993)
The world has always wanted to know what Dylan thought of it. Dylan rarely complied. He does give an honest answer on “World Gone Wrong.” Here, Dylan really sings the blues. He almost returns to the world of protest songs as well. It’s not the perfect mix, but it’s a spirited performer delivering tunes like “Blood In My Eyes.”

“Planet Waves” (1974)
“Planet Waves” is another album that got lost in the shuffle of numerous 60s and 70s Dylan releases. But it’s an enjoyable record.
For one thing, it contains the colossal “Forever Young.” Songs like “Something There is About You” are also good.
But on paper, this should’ve worked better. It was the album reuniting Dylan with The Band, after all. “Planet Waves” is good, but I wouldn’t expect to feel overwhelmed.

“Infidels” (1983)
On “Infidels,” is still the songwriter with too much great material. Maybe that’s why a song as great as “Blind Willie McTell” didn’t even make the cut.
But fans were just happy to have Dylan make non-secular, non-religious music again. There are some real gems, like “Jokerman” and “Sweetheart like You.” But it doesn’t sound like the man himself is fully committed for this one the whole way through.

“Oh Mercy” (1989)
Dylan never gave many interviews. That created a lot of mystique around the man. Each new release only deepened that.
His memoir would reveal that 80s Dylan was a man unsure of his spiritual or artistic direction. “Oh Mercy” was a clear attempt to capture the greatness of old. Daniel Lanois, a master of roots rock, came in to produce.
It shows Dylan really trying for a change. “Most of the Time” is a great song. So is “Shooting Star.” But some of the truly great Dylan material was, luckily, around the corner.

“Empire Burlesque” (1985)
Dylan didn’t care about his talent for a long time, until only traces of it were revealed. In the 1980s, Dylan began to doubt himself.
The doubts are the reason for the dated 80s production. But this time, the songs are excellent. “Tight Connection to My Heart (Has Anybody Seen My Love?)” is a great pop-rock tune that he ought to have gifted to The Rolling Stones. “Emotionally Yours” and “Dark Eyes” are two of the best songs he wrote in years.
It didn’t turn Dylan into a pop star. He wouldn’t quite try so hard again. But his love for penning the songs was slowly coming back.

“Tempest” (2017)
Bob Dylan is very much a part of the modern pop-rock vocabulary. So much so, that the songwriter needed to go back to musical styles popular before his time in order to find something fresh.
“Tempest” is the most retro-inspired of all the records of original material released post-2000. This may prove a challenge for some. But hearing them is rewarding.
For one thing, Dylan is lyrically sharper and meaner than he has been in a long time. At this stage in his career, it seems that it’s the stories of love and murder that most interest him.

“Street Legal” (1978)
Dylan occasionally gets sick of being Dylan. That’s what “Street Legal” felt like. And, post-punk-rock, some of his followers had shifted their focus anyway.
It’s a shame, really, because some of the songs here are superb. The evil swamp blues of “New Pony” is great. “Changing of the Guards” and “Senor (Tales of Yankee Power)” made great additions to the discography.
But, overall, “Street Legal” doesn’t quite have the bite and energy that Dylan had proven on still possessed in his mid-70s records. I’ve always thought that the album cover was great though.

“Bob Dylan” (1962)
Could you really hear the man he was to become? Can you really hear the great songwriting? Yes and no. What you can hear is a lot of Woody Guthrie admiration. But Dylan’s ability to pick classic songs and work on his own also proved on “Bob Dylan” that he was already a cut above the rest of the other folkies.

“Together Through Life” (2009)
You get Dylan on a roll, and here’s what you get. “Together Through Life” isn’t revolutionary material for a change. But I really think that you can hear Dylan having a good time here. And this shows up in the quality of the songs.
“Beyond Here Lies Nothin'” is a highlight. Dylan has made a commitment to make this songwriting business his life and work. And, for a change, his happy with his decision.

“New Morning” (1970)
“New Morning” is a rarity – an underrated Bob Dylan album. And while the other country-rock records made around this time are often more famous, this contains some great songs.
The sound throughout is comparable to the folk-rock easy tremble of George Harrison or The Band. In fact, Dylan sang “If Not for You” with Harrison. But, “The Man in Me” and “New Morning” could’ve done just the same.

“Modern Times” (2006)
“Modern Times” was another excellent, highly-publicized release. Dylan could’ve put out anything at this stage. The world would be guaranteed to listen. But there was no certainty that they’d like it. Dylan fans have been taught to ask for the best.
Luckily, “Modern Times” is an eccentric album, but one filled with great songs. ‘Thunder on the Mountain” is vintage, adventurous Dylan. Elsewhere, the writer takes on inspiration from American blues and country tradition for songs like “Nettie Moore,” “Spirit on the Water” or “When the Deal Goes Down.”
Dylan was making great music and all was again well in the world.

“Another Side of Bob Dylan” (1964)
You can tell that Bob Dylan was becoming conscious of his influence outside of the folk scene. That’s perhaps why perhaps why pop-rock bands like The Byrds would cover several of the songs on “Another Side of Bob Dylan.”
On this one, Dylan explores more with his lyrics and music. Many of the songs are sensational. “My Back Pages,” “All I Really Want to Do,” and “Spanish Harlem Incident” are real highlights.
Dylan would feel so brave after this that shifting to a full-fledged electric rock style was just the natural follow-up.

“Time Out of Mind” (1997)
Dylan has been called a prophet. And some of you might chuckle. But it is true that many do earnestly treat him as their guru. Some of these people were losing patience with the mysterious singer in the 1990s.
“Time of Mind” was a return to form. And all of the world’s music press was desperate to hail it as such. Consequently, the album received incredible reviews upon its release.
I understand the cult for “Time Out of Mind.” While not a faultless album, it contains some songs that show Dylan more interested in songwriting than he’d been in a while. “Not Dark Yet” is a masterpiece. “Cold Irons Bound” or “Love Sick” are excellent as well.

“Love and Theft” (2001)
The world eagerly awaited this 2001 release. Had Dylan rediscovered his passion. Or was he just putting people on the way he’d done in the past?
As it turns out, “Love and Theft” marked the start of a new golden age for Dylan. The songwriter is wrestling with life’s big questions again. But you and I can tell when Dylan is really interested. That’s when his wit shines through. “Mississippi” is a real highlight and gallows humour of the chorus shows the songwriter having a good time making music again.

“Rough and Rowdy Ways” (2020)
Dylan continues to shock and amaze even 60+ years after releasing his first album. Who ever thought that, possibly, the greatest songwriter in the world still has it in him to produce 2020 one of his best albums? And, indeed, “Rough and Rowdy Ways” is one of the best releases of all-time.
The shock comes from just how playful Dylan’s lyrics are or how open he is to discussing his own legacy in songs like “False Prophet” or “I Contain Multitudes.”
What is also surprising and was pleasing to many is how much this sounds like a rock record. While Dylan was obsessed with old blues, folk etc., for a long time, “Rough and Rowdy Ways” sounds like a mischievous, rocking good time for the most part.
And, when it’s not fun, that’s for good reason. “Murder Most Foul” sounds like Dylan taking up the challenge of writing a classic. He does. Obsessed critics will be pouring over this for years to come.

“John Wesley Harding” (1967)
Dylan was brave, brave man. So brave in fact, in my estimation, that he followed up the success of his rock-era with, essentially, a country record.
Hearing “John Wesley Harding” must’ve been a shock to most of the troubadour’s fans. But on the Summer of Love, Dylan took a sharp turn.
It’s generally a laidback sound. But the songs are great. Highlights include “I Dreamed I Saw St. Augustine,” “The Wicked Messenger”, and the Jimi Hendrix-covered “All Along the Watchtower.”

“The Freewheelin’ Bob Dylan” (1963)
No other songwriter wrote more great songs than Dylan from the early 60s until the mid-70s. This is the place, I believe, where that run starts.
The 1963 Dylan is no longer as obsessed with Woody Guthrie as he was on his debut. But he’s clever, funny, and well aware of this. Just listen to “Bob Dylan’s Dream” or “Don’t Think Twice, It’s Alright.”
But it’s the start of Dylan as a defender of civil rights. He is asking for peace and pointing his figure at crooked leaders on “Masters of War.” He is imagining the consequence of war in the excellent “A Hard Rain’s A-Gonna Fall.” And, most famously, he sings of a world-changing in “Blowin’ in the Wind.”

“Nashville Skyline” (1969)
Many fans of the leather-jacket, rock-playing Dylan were upset with him when he made another full-fledged country album. But, to fans of country music, it proved that the best songwriter in the world was one of them.
I think that there are plenty of great songs for those willing to give it a chance. “Girl from the North Country” and “I Threw It All Away” are here. And “Lay Lady Lay” became one of the most surprising Dylan hits.

“The Basement Tapes” (1975)
“The Basement Tapes” was a mythical bootleg. It travelled from fan to fan. It seemed to reveal some deeper meaning – what Dylan might’ve sounded like without the mythical motorcycle crash that had taken his time and some of his artistic bite.
I know that this is technically a compilation. But time has erased that. Instead, it’s Dylan at his most relaxed. He is playing with The Band, and, generally treating the musicians them as equals.
I don’t think that there are highlights. Instead, the focal point is how Dylan and the Band start, stop and stumble through extraordinary songs that might’ve never seen the light of day.

“The Times They Are a-Changin'” (1964)
Bob Dylan, in some ways, usurped the New York folk movement. By 1964, he is was its king. And he knew just what the scene needed – songs be to sung in the streets.
“The Times They Are a-Changin'” contains some of Dylan’s finest protest songs. These include “Blowin’ in the Wind,” “The Lonesome Death of Hattie Carroll” or “With God on Our Side.”
These are generationally important songs. They’d be sung at every protest march across the U.S.A. I’m impressed by the songwriting at even such a young age. But Dylan himself would also need to survive a few assassination threats before he could rid himself of the folkie persona.

“Desire” (1976)
Bob Dylan was so used to quickly coming up with classics that he rarely spent time on songs. While other songwriters would treasure nearly any of the tunes on “Desire,” Dylan throws them into the world. It’s almost as if he’s saying, “You bet that there’s more where this came from!”
In my estimation, “Desire” contains some of Dylan’s best 1970s material. “One More Cup of Coffee (Valley Below),” “Isis,” or the protest rock of “Hurricane” are astounding.
The juice of “Blood on the Tracks” is still flowing, yes. However, some of the other songs are disposed of a little too easily. Still, how many other songwriters ever wrote something like “Mozambique?”

“Bringing It All Back Home” (1965)
“Bringing It All Back Home” was, of course, the revolutionary rock album. It’s the fabled release on which, supposedly, Dylan turned his back on folk and acoustic guitar.
While Dylan had begun experimenting with sounds outside of classic folk on “Another Side of Bob Dylan,” it’s true that this is a wild departure and provocative statement.
It’s not just the fact that songs like “Maggie’s Farm” or “Outlaw Blues” sound like garage rockers. It’s the freedom that the songwriter allows himself lyrically. Mythical characters and ordinary villains all find themselves wrapped in the same story. “Bob Dylan’s 115th Dream” is a reimagining of the discovery of America. “Mr. Tambourine Man” is about performers who can steal your heart away. “The Gates of Eden” is about the afterlife.
But had any singer quite motormouthed through lyrics as on “Subterranean Homesick Blues”? I don’t think so.

“Highway 61 Revisited” (1965)
The formula that Dylan had invented for himself on “Bringing It All Back Home” got perfected on “Highway 61 Revisited.” This was impressionist poetry, surrealism and political commentary all coming together in, usually, hilarious fashion.
In fact, the songs here always make me chuckle. “Like a Rolling Stone” may just be the most celebrated pop-rock song ever made. But it was, first, a payback against a rich, aloof female aristocrat.
“Tombstone Blues” paints the Apocalypse as a comedy. “Ballad of a Thin Man” murders all of Dylan’s music critics in one decisive move. And “Desolation Row” imagines a world where folk heroes get hung, and Cinderella sweeps the streets.
I’ve never heard a funnier album. This is Dylan giddy about truly finding his voice. And were it not for his other achievements, it would be number one on my list, ranking the very best Bob Dylan albums.

“Blood on the Tracks” (1975)
On “Blood on the Tracks”, Bob Dylan found his groove back. He delivered songs that rivalled the best he’d written in the 1960s.
Bob Dylan was a legendary figure in the 1970s. But some had written him out of his own story. Maybe he had actually crashed his motorcycle. Maybe he was actually sick of being Bob Dylan.
Wounded by the impending doom of his marriage and high on high-brow poetry, Dylan stumbled onto one of his very best collections of songs.
He’s no longer funny except when he’s bitter. “Tangled Up in Blue,” “If You See Her, Say Hello”, or “Idiot Wind” show Dylan at his meanest. His settling scores here.
But he’s marvellously tender as he hopelessly sings words of love on “Shelter from the Storm” or “Meet Me in the Morning.”
And for anyone trying to write the big Dylanesque storyline song, “Lili, Rosemary and the Jack of Hearts”, proved nobody could out-Dylan him.
I think that it’s a sensational album. Many share my opinion. In fact, any fan of pop-rock ought to own “Blood on the Tracks,” as well as the following three albums.

“Blonde on Blonde” (1966)
“Blonde on Blonde” sees Dylan’s genius songwriting, taking advice from everywhere and pointing its aim in every direction. It’s the pinnacle of one of the most fruitful periods in rock history. The due would have to be paid soon enough through burnout. But in 1966, nobody, not even The Beatles, could conceive of writing perfect mini-novels in song form the way Dylan did.
It’s the album I’ve loved most from the moment I discovered his work. It’s an album that keeps rewarding the devoted listener.
The fact is that Dylan, like The Beatles on “The White Album,” takes on all styles of music. And, I think that he conquers them all. There are the ballads of “Visions of Johanna” and “Just Like a Woman.” There’s the hazy circus-rock of “Rainy Day Women #12 & 35.” There’s the pop of “I Want You.” And there are more than a few moments when The Band & co. create a sensational mixture of all these genres.
“Blonde on Blonde” is hard to top, and impossible to plan. It’s dangerous to estimate if anything like it will come again. It is, for me, Bob Dylan’s greatest album, and one of the great works of art.