Almanac Music: Bob Dylan Top 20



Inspired by Smokie Dawson’s recent post listing his favourite 50 Rolling Stones songs, I thought I’d create a Bob Dylan list.  


However, my list is not as ambitious as Smokie’s as it turned out to be a lot more difficult than I expected so I settled upon a top 20. There is the firm half dozen or so favourites that readily come to mind to automatically be in my top 20 then after that any from the many 100s recorded.


As Bob recorded nearly 1000 songs provides a considerable body of work to select from with rarely a dud amongst them, I could have created a dozen different favourite lists. 


Depending on the mood I’m in depends which Dylan songs are played, and naturally they are for ever changing though the firm favourites always remain at the top of the list. 


After much consideration I’ve come up with a top 20. Here they are listed in order of preference.


1.‘Positively 4th Street’
I remember thinking ‘wow’ when I first heard this song. Such a bitter and biting reflection of feeling cheated. Many believe it is a response to Joan Baez, however Clinton Heylin (1) suggests it’s a reaction to the response Dylan received from fans at Newport when he went electric on stage. Originally slated to appear on Highway 61 Revisited  but dropped from the final release. It was released as a follow up to ‘Like A Rolling Stone’  in 1965.


2.‘Queen Jane Approximately’
One of the many fantastic tracks from Highway 61 Revisited.  


3.‘Desolation Row’
The words and imagery reflect Bob the wordsmith at the peak of his powers.


4.‘Like A Rolling Stone’
I have to thank a former teacher for introducing this song and Bob to me. Read the story here.


5.‘I Dreamed I Saw St Augustine’
I eagerly awaited the release of John Wesley Harding in early 1968. I walked into Allans Music store in Elizabeth St Melbourne and purchased a copy from a display on the front counter. I could not wait until I got home to play the album. Expecting it to be similar to Blonde On Blonde I was surprised on first playing by the change of direction by Bob. Not what I expected but it quickly grew on me.


6.If You See Her Say Hello’
For me this was the standout track from Blood On The Tracks.


7.‘I Threw It All Away’
From Nashville Skyline Bob’s follow up album after John Wesley Harding and continued his move to more of a country feel with his music. He utilised top session musos from Nashville for the album.


8.Workingman’s Blues#2’
This is the only song included on my list that is not from the 60s or 70s. From Modern Times released in 2006.


9.‘She Belongs To Me’
From Bringing It All Back Home released early 1965.


10.‘Love Minus Zero/No Limit’
Also from the Bringing It All Back Home album.


11.‘When The Ship Comes In’
From the Times They Are A-Changing album released January 1964. The Clancy Brothers and Tommy Makem do a great version of the song.


12.‘Forever Young’
I bought Planet Waves when I was living in London in 1974. This song reminded me of the loved ones I was missing back home. The Band backing Bob.


13.‘Mr Tambourine Man’
Another great tune from the Bringing It All Back Home album. And of course, The Byrds really put Dylan on map with their great rendition of the song.


14.‘Absolutely Sweet Marie’
Love the driving beat that pushes this song along. From Blonde On Blonde released in 1966.


15.‘One Of Us Must Know (Sooner Or Later)’
The swirling organ really attracted me in this song. Another great tune from Blonde On Blonde that reflects his search for ‘that wild mercury sound’. (2)


16.‘Most Likely You Go Your Way And I’ll Go Mine’
From Blonde On Blonde. 


17.‘Changing Of The Guards’
From Street-Legal released in 1978. One of the few Dylan songs with brass on the track. Works well.


18.‘Boots Of Spanish Leather’
Bob at his best with just an acoustic guitar singing a love song.


19.Lay, Lady, Lay’
This song really bowled me over when I first heard it. Bob was experimenting with his voice and this was quite different from previous recordings. From Nashville Skyline released in 1969.


20.‘You Ain’t Goin’ Nowhere’
From The Basement Tapes recorded 1967.


Here is a link to Col’s Dylan Top 20 playlist


When preparing a Spotify playlist of my Bob favourites I thought it would be interesting to create a playlist of the 20 most played Bob songs on Spotify. The figures staggered me, and surprised me as well. Here they are in order of the number of plays.


1.’Like A Rolling Stone’   (244,081,427  plays)

2. ‘Knockin’ On Heavens’ Door’    (224,815,328)

3. ‘The Times They Are A-Changin’’    (163,502,478)

4. ‘Hurricane’    (152,570,943)

5. ‘Blowin’ In The Wind’    (128,345,930)

6. ‘Girl From The North Country’    (106,380,408)

7. ‘Don’t Think Twice, It’s Alright’    (83,930,766)

8. ‘Mr Tambourine Man’    (75,571,650)

9. ‘Tangled Up In Blue’    (69,042,940)

10. ‘Lay, Lady, Lay’    (64,101,752)

11. ‘Shelter From The Storm’    (60,874,637)

12. ‘The Man In Me’    (40,247,217)

13. ‘I Want You’    (35,801,743)

14. ‘Subterranean Homesick Blues’    (31,460,521)

15. ‘A Hard Rain’s A-Gonna Fall’    (25,871,045)

16. ‘All Along The Watchtower’    (23,910,297)

17. ‘Must Be Santa’    (22,215,064)

18. ‘Simple Twist Of Fate’    (22,204,398)

19. ‘Forever Young’    (20,639,743)

20. ‘One More Cup Of Coffee’    (19,534,178)


Here is the link to the Spotify Dylan Top 20


  1. 1.Heylin, Clinton  Dylan Behind Closed Doors: The Recording Sessions [1960-1994] Penguin Books, London, 1995
  2. Ibid


More from Col can be read here.


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About Colin Ritchie

Retired teacher who enjoys following the Bombers, listening to music especially Bob Dylan, reading, and swimming.


  1. A lof of 1965 there Col. It’s impossible task, isn’t it. I tend to think top 20 albums when I think of Dylan, but I must say I’m very happy to see something from ‘Street Legal’ on your list – a most underrated album, its biggest crime is that it is sandwiched between ‘Desire’ and ‘Slow Train Coming’. Maybe in 100 years time people will realise how great it is.

  2. Colin Ritchie says

    A tough task indeed DB! I’m quite happy with the first half-dozen or so selections, they are firm and would always be in my top 10, the others are fluid often depending on my mood etc. I must admit I’ve come back and started listening to albums that in the past have been in the background for me, and I’ve been pleasantly surprised. I’m planning to visit the Bob Dylan Centre in Tulsa as part of a New Orleans JazzFest tour next year, and is something I’m looking forward to.

  3. Good job Col. How do you select the 20 best from the career of a person who first recorded before I was born? It’s been a sterling career.

    The first Dylan song I was attracted to was Hurricane. Eight and a bit minutes of a stirring tale of injustice backed by a cacophony of musical sounds. This back in the summer of 1975-76 when I was early on in high school.

    From your 20 I’d take Lay Lady Lay. There’s a great live version from the time of the Rolling Thunder Review.

    I noticed DB commented on a lot of 1965 in your selections.I turned two that year so Mr Zimmerman was literally not on my radar.

    Keep them coming Col.


  4. A might fine list, Col.
    “Desire” and “Blood on the tracks” are particular favourites of mine.
    “Tangled up in blue” would be close to the top of my Dylan list.


  5. Big fan of the Modern Times album. Agree with Workingman’s Blues, but the whole album is beautiful love songs for us ageing boomers. “Beyond the Horizon” and “When the Deal goes Down” are all about celebrating what we have while we still have it. Gets me teary.
    Would also give an honourable mention to some of his songs – but in the version recorded by The Band. “I Shall be Released” and “Tears of Rage” get me every time.
    “Blind Willie McTell” and “Ring them Bells” are other faves.

  6. CR, excellent. And not just because Queen Jane is in there.

    DB reckons Streel Legal is under-rated, tell him his dreaming.

    You could put the whole of Nashville Skyline in there and I would be satisfied.

    By the way, your list would be a whole lot betterer or it would be mine if it included Idiot Wind, Visions and Mississippi.


  7. A couple of obscuro favorites of mine: Romance in Durango from ‘Desire’ (the Marty Robbins ‘El Paso’ story retold with infinitely better music behind it, turning a schlocky melodrama into an epic), and Tomorrow Is A Long Time (not sure what album Zimmo put it on but Rod Stewart made it the last track of Every Picture Tells a Story).

    Worst Dylan song ever: ‘Joey’, all 7:40 of Manilowesque over-production, and all over a Mafia hit-man, coincidentally straight before R in D on ‘Desire’, must be close.

    Where Are You Tonight is another very good song on Street Legal. Unfortunately there are too many very bad ones for it to be among the ATGs – and yes, I am happy to name that schmaltzy, sanctimonious dirge (that manages to rip off two different Neil Young melodies within the same song) ‘Is Your Love In Vain’

    For mine, Bob never topped Like A Rolling Stone – and neither did anybody else, including the Beatles.

  8. “Lily, Rosemary and the Jack of Hearts” has always been a favourite for its witty and compelling storytelling. It’s a great narrative. Hearing it as a teenager it was cinematic in its scope and realisation for me in a way that many celebrated films were not. It’s perfectly sequenced after the bluesy swagger of “Meet Me in the Morning” and (Col’s pick) “If You See Her, Say Hello.”

  9. Peter Crossing says

    Terrific list, Col. Everywhere you look in Dylan’s catalogue there are great songs – with lyrics that contain wonderful images or tell a story or are bitingly clever or sardonic.
    Often, a quirky or whimsical line in a song that may not make the list of “greatest”.
    “An’ I told you, as you clawed out my eyes that I
    Never really meant to do you any harm”
    And they make you think.
    “There’s no success like failure, and failure’s no success at all”
    Texas medicine vs railroad gin.
    Motorpsycho Nightmare is a classic.
    The sparse desolation and sadness of The Ballad of Hollis Brown.
    High Water (For Charley Patton) is a wonder and harks back to Blind Willie McTell and Down The Highway.
    And a vision of America’s future in the final lines of Bob Dylan’s 115th Dream.
    Complementing the lyrics are the brilliant instrumental touches in many of the songs: Michael Bloomfield’s lyrical, swooping guitar on Like Rolling Stone and Tombstone Blues, Charlie McCoy’s acoustic intro on Desolation Row, Scarlet Rivera’s violin on Hurricane, the deft harmonica on so many songs, the solo piano of When I Paint My Masterpiece.
    And so it goes.

  10. I have been giving ‘Its alright, Ma (I’m only bleeding)’ a bit of a run of late.
    A lot of the culture that he gives a serve to is still relevant today.

  11. Trevor Blainey says

    Col, I’ve become a Bob fan late in the piece having had an epiphany years ago after i saw him live the one and only time at a weird venue outdoors at a festival behind the Melbourne Exhibition Centre. way past his best but mesmerising nonetheless with a crack band. I’ve since gathered up all the famous albums and most of those from the last 15 years. Last year’s Rough and Rowdy Ways is a cracker. I compiled this (probably overlong) Spotify playlist that i call Not Quite Bob for my mates who are much more longtime fans. Didn’t understand my early reticence etc. You and some of the Bob nuts here might get a kick out of it.

    NB: not all tracks here are representative of Bob but it’s the influences innit.

    regards, Trevor

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