Bob Dylan's Best Albums of the 1960s: Ranked

Bob Dylan needs no introduction – he’s one of the key figures in rock music. He helped to define the genre as it matured, especially as a lyricist. He broadened the scope of rock lyrics, utilising both social issues and surreal poetry.

Through the 1960s, Dylan never stood still, initially transitioning from coffee-house folk to protest songs. After four solo acoustic albums with his guitar and harmonica for accompaniment, Dylan abandoned acoustic folk. He started using full bands, and produced acclaimed, inspired albums of electric beatnik poetry. After a mysterious motorcycle accident, Dylan retreated from the limelight and embraced family life, producing a pair of very different acoustic albums to close out the decade.

Bob Dylan was frighteningly prolific in the 1960s – I haven’t included The Basement Tapes, recorded with The Band in 1967 but not released until 1975. Dylan also released non-album singles like ‘Positively Fourth Street’ and ‘Can You Please Crawl Out Your Window?’, and a ton of outtakes later surfaced on archival releases.

Here are my rankings of Dylan’s albums from a decade during which he never stood still:

The Times They Are A-Changin

Songs like ‘Blowin’ In The Wind’ and ‘Masters of War’ had established Dylan as a protest singer, and he followed them up with a dour, humourless record that’s a tough listen. There are strong songs like ‘Boots of Spanish Leather’ and ‘When The Ship Comes In’, but it’s tough to sit through lengthy diatribes like ‘The Lonesome Death of Hattie Carroll’.

Nashville Skyline

Dylan’s final album of the 1960s was a light-hearted country collection. It’s notable for Dylan’s different voice – he’d stopped smoking temporarily, and utilises a deeper country croon. There are a couple of strong songs here – ‘I Threw It All Away’ is a strong single that’s now half-forgotten, while ‘Lay Lady Lay’ is the best-known piece. A lot of Nashville Skyline is tuneful, but not among Dylan’s most substantial work.

Bob Dylan

Bob Dylan’s debut album is almost entirely made of covers, and it’s a good sampler of the Greenwich Village folk clubs in New York. The young Bob Dylan’s provides enough charisma to add life to these well-worn folk songs. He also slips in a couple of originals that hint at his potential as a writer – ‘Song For Woody’, dedicated to role-model Woody Guthrie, is a surprisingly honest moment from an often cryptic man.

Another Side of Bob Dylan

Another Side is Dylan’s last completely solo album. The more complex songs often sound like they would have benefited from full band arrangements, and his vocal limitations are exposed as he navigates through more expansive melodies. But there are lots of great songs here; ‘All I Really Want To Do’ and ‘My Back Pages’ would later be covered by The Byrds. The eight minutes of ‘Ballad of Plain D’, on the other hand, is the most excruciating song from Dylan’s 1960s catalogue

Bringing It All Back Home


We’re only halfway through the list and we’re already into the heavy hitters. Dylan’s first electric album still features a largely acoustic second side, with ‘It’s All Right, Ma (I’m Only Bleeding)’ and ‘Mr Tambourine Man’, while the first side has highlights like ‘Maggie’s Farm’, ‘Subterranean Homesick Blues’, and ‘Love Minus Zero/No Limit’. Bringing It All Back Home is an excellent record, but Dylan made four even better albums during the decade.

Highway 61 Revisited

There’s a strong case that Dylan’s first fully electric album has the strongest bookends of any record in popular music – it opens with the sneering put-downs of ‘Like A Rolling Stone’ and closes with the austere, literary desperation of ‘Desolation Row’. It’s not bad in between either, with the silliness of ‘Tombstone Blues’, the strange and sinister ‘Ballad of a Thin Man’, and ‘Just Like Tom Thumb Blues’ backed by great musicians like Al Kooper and Mike Bloomfield.

John Wesley Harding

When Dylan re-emerged into the public eye after his motorcycle accident, he was less of a strung-out beatnik and more of a backwoods preacher. Dylan cut an album of mystical, low key pieces in Nashville, with a simple three-piece band. It doesn’t sound pre-possessing, but it’s one of his finest albums, full of economical and enticing storytelling. The most famous song is ‘All Along The Watchtower’ – Dylan’s version wasn’t a hit, but Jimi Hendrix electrified it, both figuratively and literally.

The Freewheelin’ Bob Dylan

At his second turn at bat, Dylan turned in a batch of terrific songs that hold attention even with his simple guitar, harmonica and vocal presentation. Early Dylan is best characterised by the protest folk of ‘Blowin’ In The Wind’, ‘A Hard Rain’s A-Gonna Fall’, and ‘Masters of War’; has there even been a nastier, yet more justified line than “even Jesus would never forgive what you do?” But there’s also the English folk inspired ‘Girl From The North Country’ and the perfectly weighted kiss off of ‘Don’t Think Twice, It’s Alright’. “I gave her my heart, but she wanted my soul.”

Blonde on Blonde

Rock’s first double album is also one of the only double albums to be almost devoid of filler. There are fun blues songs, like ‘Leopard Skin Pillbox Hat’ and ‘Stuck Inside of Mobile with the Memphis Blues Again’, with great backing bands, including Robbie Robertson’s searing guitar. But at the heart of the album are the intricately developed acoustic pieces, ‘Visions of Johanna’ and the beautiful closer ‘Sad Eyed Lady of the Lowlands’, my pick for the best song in an illustrious career.

Dylan certainly had his moments after the 1960s, especially in the mid-1970s with Blood on the Tracks and Desire. My favourite Dylan album, however, is the archival release of his 1966 “Royal Albert Hall” concert.

Do you have a favourite Dylan record?

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  1. My Mount Rushmore of Dylan would be- Blonde On Blonde/ Highway 61 Revisited/ Blood On The Tracks/ Freewheelin’ Bob Dylan… at least for today!

    • Obviously similar to mine – I have mixed feelings about Blood on the Tracks (I feel I say this a lot, but I really hate the bass line for Lily, Rosemary and the Jack of Hearts) – the bright country arrangements work for some songs, but not others. Great collection of songs though.

  2. Great idea. Haven’t thought about it much but generally speaking, I’d probably rank them as 1, Highway 61, 2 Blonde On Blonde; 3, Bringing it All Back Home, 4, Freewheelin’, 5, Nashville Skyline. From there on, roll the dice. Haven’t listened to all them in a while so, hard to rank the rest.

  3. Hard to argue with that sequence, although on any given day numbers 1 through 6 could swap places. During my teens, from the late-’70s through ’82, I only had his Greatest Hits album. The first non-compilation I owned was Infidels, which remains in my all-time Dylan Top 5. Desire and Blood On The Tracks are up there for me as well, along with latter-day classics like Love & Theft and Modern Times. I also have a weird affinity for his Christmas album, much to my wife’s chagrin. And many of the Bootleg Series releases are as good as any proper album.

  4. Good round-up! Freewheelin’ is my current favorite albeit I haven’t yet listened to Blonde, Nashville, Another Side or Bringing. The Times They Are A-Changin’ has its moments, but I agree the LP is a bit of a chore. I still don’t know what to make of John Wesley Harding, a record that rewards repeat listens due to its enigmatic lyrics, I like the drumming and harmonica even though the album is hard to grab hold of in terms of melodies.

    • #4 does seem low for Highway 61 Revisited, but there’s an embarrassment of riches there. As I said in another comment, all of the top 5 are great albums that could make a strong case for the top spot.
      I have a bootleg of Blood on the Tracks of the New York Sessions. I like the more polished final versions in some instances (like Tangled Up In Blue) but not so much in others (Lily Rosemary and the Jack of Hearts – hate that country bass playing in such a long song). Feel like if I could pick and choose an album from the two different sessions, it would be one of his very best, but in its finished configuration it might struggle to make the top 5 above any of the big 1960s releases.

  5. Great idea.
    I don’t think I’d argue with this breakdown with the only exception of John Wesley Harding as I’ve not spent much time with that one, I’d probably drop it back up the list some

  6. I would put Highway 61 and Bringing It All Back Home above JWH and Freewheelin’, but they are very special albums and this is a great list!
    I guess my biggest disagreement would be regarding the placement of The Times They Are A-Changin’. I know that it is often viewed as Dylan’s weakest 60s album alongside his debut, Nashville, and JWH (not because they are bad, but because they are the least classic in a massive run of classics), but I actually love all tracks in The Times They Are A-Changin’, including The Lonesome Death of Hattie Carroll.
    Dylan never again made such a heavily political album; a decision I can understand given all the problems he had with people who tried to make him “the voice of a generation”. But I really like that side of his, and I love how dark the album can get (Ballad of Hollis Brown sends shivers down my spine) while being very defiant as well (the title track). If I were to choose the weakest link among his 60s output, I would pick Another Side of Bob Dylan. For some reason, I never warmed up to it as a whole, even if I love a handful of tracks in there.

    • Another Side of Bob Dylan is an interesting one – it has a bunch of really good songs, but he was outgrowing the acoustic format. It’s the one album where his voice really bothers me, as he’s doing more complex songs, but his vocal limitations are exposed with the low key backing. Throw in a full band on some songs, and drop Ballad in Plain D, and it would be a whole lot more enjoyable.

      • That’s a good analysis, and you are right about what would make it more enjoyable.
        To perhaps support your point, I had never really cared for Spanish Harlem Incident until I heard The Byrds’ take on the song. Now I love the tune and quite appreciate the Dylan original.

  7. I find much of his really early stuff dry and uninspiring, but obviously the Byrds, Hendrix etc. saw things in it and gave songs their own treatment with spectacular results. Highway 61 Revisited is my favourite from the 60s but I wouldn’t take even that to a desert island. Blood on the Tracks, Desire and the 1976 live album Hard Rain are much more approachable for me.

  8. What a wealth of great music. I’ve been stuck in a Tom Russell spin cycle. I tune into your take and while reading it Tom comes on my player and sings ‘Jack Of Hearts’ with another one of my favorites, Joe Ely (Townes cousins). Yeah those first few albums I can’t listen to without hearing Woody.

  9. Admittedly, I have somewhat mixed feelings when it comes to Bob Dylan. On the one hand, there are many songs I really dig. Many of them are on the albums you highlighted. Then there’s other music I’ve heard from him that’s definitely not my cup of tea.
    I guess I also haven’t forgotten my bitter disappointment about the only Dylan concert I’ve ever been to. It was in Germany in the late ‘80s. Dylan opened his set with “Knocking On Heaven’s Door” and then only played stuff I didn’t know.
    To “prepare” for the show I had listened to “Before The Flood” to the point where I knew that album in and out. Naively, I thought it would be representative of what I could expect for “my” concert.
    Afterwards, a friend and Dylan fan cheerfully told me that Dylan is known for being unpredictable and basically doesn’t give a shit.
    Luckily, Roger McGuinn and Tom Petty and the Heartbreakers were on the ticket as well and saved the night!

    • The 1960s is generally acknowledged as his strongest era, although he had a comeback in the mid 1970s with Blood on the Tracks and Desire. It’s not an uncommon pattern to do your best work in your first ten years, it’s just his later career gets a lot of attention because he’s Dylan.
      I saw him in 2003. I got a pretty normal setlist with stuff from his OK newest album at the time (Love and Theft) and chestnuts like ‘My Back Pages’ and ‘Desolation Row’. It felt a little perfunctory, but I still enjoyed it.

  10. I’m loving these worst to best rankings. I did one for Wilco once and it took FOREVER to decide.
    Anyway, Highway 61 is my easy #1 for 60s Dylan and I’ve also always thought Another Side is underrated. To Ramona is one of my all time favourites and I actually really like Ballad in Plain D (yeah, I said it – something about that song just clicks for me, even when the lyrics get goofy).

    • Glad you enjoyed them! I haven’t done one for a while, but usually I review and rate the albums first then post the worst to best as a summary, which makes things easier. For me with Dylan’s 1960s, there are two clear tiers – the top five (Freewheeling, the four albums from 1965-1967) are way ahead of the other four for me. Another Side is very good in places, but I think some of it is really asking for full band arrangements.

  11. 09: Nashville Skyline
    08: Bob Dylan
    07: John Wesley Harding
    06: The Freewheelin’ Bob Dylan
    05: The Times They Are a-Changin’
    04: Another Side of Bob Dylan
    03: Bringing It All Back Home
    02: Blonde on Blonde
    01: Highway 61 Revisited

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