My Favourite 50 Bob Dylan Songs

Before you start reading I would like to point out that I mainly write about films, not music. In the process of writing this I looked back over what I've written and saw what I wrote. I saw the same kind of writing to my first movie reviews. I hope this isn't a deterrent but I do hope my love Dylan comes through.

Bob Dylan was born on May 24, 1941 in Duluth, Minnesota, U.S.A. He grew exposed to musicians such as Woody Guthrie, Johnny Cash, and Hank Williams. He moved to New York after high school and made his first record 'Bob Dylan', which mainly consisted of covers. It was a moderate success. His second album however 'Freewheelin' Bob Dylan' did a lot better. This time he wrote most of the songs. He was instantly hailed as songwriting genius for songs like 'Blowin' in the Wind' and 'A Hard Rain's A Gonna Fall'. His songs were picked up by protest movements as their anthems. He made a couple more folk records before doing an informal trilogy of rock albums that would divide his fans.

These albums didn't focus on social change but rather were more self reflective. After these records he would have career ups and downs, good albums and bad ones but he always had good songs. Even when he was making gospel music he would release gold. This consistency over five decades has also lead to him becoming of the most hailed songwriters of all-time. He has his fair share of Grammies but he also has an Oscar and even a Nobel prize.

I spend most my time thinking and writing about film. I'm also predominantly influenced by people who write and make films. The main exception is Dylan. His writing has often inspired my (so far) small creative output.

I haven't listened to all of Dylan's albums yet and I'm sure between now and this time next year this list will change substantially. Especially, as I delve into his back catalogue more. So make of it what you will.

A playlist of all the songs on the list can be found at the end.

50. Masters of War (Freewheelin' Bob Dylan)

Best Line: Even Jesus would never forgive what you do

49. Tweedle Dee & Tweedle Dum (Love and Theft)

Best Line: Tweedle-dee Dum said to Tweedle-dee Dee“Your presence is obnoxious to me".

48. Idiot Wind (Blood on the Tracks)

Best Line: I noticed at the ceremony, your corrupt ways had finally made you blind.

47. It Ain’t Me Babe (Another Side of Bob Dylan)

Best Line: You say you’re lookin' for someone/Who’ll pick you up each time you fall/To gather flowers constantly.

46. Trying to Get to Heaven (Modern Times)

Best Line: When I was in Missouri/They would not let me be/I had to leave there in a hurry/I only saw what they let me see/You broke a heart that loved you.

45. To Ramona (Another Side of Bob Dylan)

Best Line: I’ve heard you say many times/That you’re better than no one/And no one is better than you.

44. Shelter from the Storm (Blood on the Tracks)

Best Line: I came in from the wilderness/A creature void of form.

43. One of us Must Know (Sooner or Later) (Blonde on Blonde)

Best Line: When you whispered in my ear/And asked me if I was leavin' with you or her/I didn’t realise just what I did hear.

42. Rainy Day Women #12 & 35 (Blonde on Blonde)

What's 12 times 35? It's mind blown.

Best Line: Everybody must get stoned.

41. Mississippi (Love and Theft)

Best Line: City’s just a jungle; more games to play/Trapped in the heart of it, trying' to get away.

40. With God on Our Side (The Times They Are A-Changin')

Best Line: I’ve learned to hate the Russians/All through my whole life/If another war comes/It’s them we must fight/To hate them and fear them/To run and to hide/And accept it all bravely/With God on my side.

39. I Dreamed I Saw St Augustine (John Wesley Harding)

Best Line: No martyr is among ye now/ Whom you can call your own.

38. If Not For You (New Morning)

Best Line: If not for you/Babe, I’d lay awake all night/Wait for the morning light.

37. Just Like Tom Thumb’s Blues (Highway 61 Revisited)

Best Line: I started out on Burgundy/But soon hit the harder stuff.

36. It’s All Over Now Baby Blue (Bringing It All Back Home)

Best Line: The empty handed painter from your streets/Is drawing crazy patterns on your sheets.

35. Farewell, Angelina (Bringing It All Back Home out take)

Best Line: The bells of the crown/Are being stolen by bandits/I must follow the sound.

34. I’m Not There (Soundtrack of Dylan biopic of the same name)

Recorded with The Band at Big Pink, this song didn’t see an official release until 2007 for the Dylan biopic of the same name. Dylan’s vocals here carries a lot of emotion… The song maybe from the basement but it echoes Blonde on Blonde. Dylan may have foregone his rock sound immediately after Blonde on Blonde but this is a great example of how it always stayed with him, albeit in a more toned down fashion.

Best Line: I don't belong to anybody/She's my prize-forsaken angel/But she don't hear me cry

33. Honest With Me (Love and Theft)

Honestly, Dylan can still rock and this is a great example. The production here holds up without Dylan’s writing and Dylan’s writing echoes his early rock days. It’s references galore and the persona Dylan has written into the song is fascinating.

Best Line: I’m avoidin’ the Southside the best I can/These memories I got, they can strangle a man.

32. I Want You (Blonde on Blonde)

Best Line: Now your dancing child with his Chinese suit/He spoke to me, I took his flute/ No, I wasn’t very cute to him, was I?

31. Don’t Think Twice, It’s All Right (Freeweelin' Bob Dylan)

Best Line: When your rooster crows at the break of dawn/Look out your window and I’ll be gone

30. Stuck Inside of Mobile with Memphis Blues Again (Blonde on Blonde)

Best Line: She said that all the railroad men/Just drink up your blood like wine

29. Lo and Behold! (The Basement Tapes)

Best Line: Gonna save my money and rip it up!

28. Hurricane (Desire)

One of the most accessible Dylan songs is oddly enough one of the most enjoyable to sing along with. It’s about Rubin Hurricane boxer framed for murder. The song had a public impact as it triggered a re-trial. Hurricane is also one of Dylan’s most overtly political song. ---

27. Mr Tambourine Man (Bringing It All Back Home)

Best Line: Yes, to dance beneath the diamond sky with one hand waving free/Silhouetted by the sea, circled by the circus sands/With all memory and fate driven deep beneath the waves/Let me forget about today until tomorrow.

26. Every Grain of Sand (Shots of Love)

Best Line: I hear the ancient footsteps like the motion of the sea/Sometimes I turn, there’s someone there, other times it’s only me.

25. Blowin’ in the Wind (Freewheelin' Bob Dylan)

How could I not pick this line?

Best Line: How many roads must a man walk downBefore you call him a man?

24. Chimes of Freedom (Another Side of Bob Dylan)

Best Line: Flashing for the warriors whose strength is not to fight/Flashing for the refugees on the unarmed road of flight.

23. Million Dollar Bash (The Basement Tapes)

While The Band and Bob Dylan were hidden away for most of 1968 this track shows they were having a great time in Big Pink and you can hear that in Dylan’s vocals and the performance of The Band.

Best Line: Well, I took my counselor/Out to the barn/Silly Nelly was there/She told him a yarn.

22. Maggie’s Farm (Bringing It All Back Home)

Best Line: Everybody says she's the brains behind Pa

21. All I Really Want To Do (Another Side of Bob Dylan)

Best Line: I don’t wanta' fake you out

20. Girl From the Country North, with Johnny Cash (Nashville Skyline)

While originally recorded for Dylan’s breakout album ‘Freewheelin’ Bob Dylan’, it’s his re-recorded version that is the defining one. Dylan had briefly quit smoking and his voice changed so much that a lot of people didn’t know it was him when they heard the song on the radio. In ‘Nashville Skyline’ Dylan went more a country root and what better way to start it off than a duet with one of the best. Johnny Cash. When listening to the song I imagine that the pair is in the studio singing and halfway through they look at each and share a moment. It’s one music’s best bromances. I have read that Dylan and Cash once spent some time recording a bunch of songs. If there’s there’s a competition for the best album never made, that has to be up there.

Dylan isn’t the most karaoke-friendly songwriter but here the essence of the song makes it perfect for a karaoke duet. Except the song isn’t a pop hit. It’s a fun song but it also has a soothing effect thanks to Dylan and Cash’s singing. It’s easily one of Dylan’s most unique songs.

Best Line: Where the winds hit heavy on the borderline

19. All Along the Watchtower (John Wesley Harding)

While the Jimi Hendrix cover may be widely considered the superior version, even by me (just), it’s Dylan’s vocal performance that Hendrix was never able to replicate. The song contains 12 lines and features plenty of Dylan’s writing tropes. Ambiguous figures (who is The Joker and The Thief?), playing around with past and present tense, and possibly some lines that chronologically belong at the end of the song.

Best Line: There are many here among us who feel that life is but a joke.

18. Highway 61 Revisited (Highway 61 Revisited)

If Queen Jane Approximately is about Dylan's mother than this is about his father. Dylan's father (whose name is Abraham) has a confrontation with God, who tells him he has to kill his first born. Who is Dylan.

Also best use of a slide whistle ever.

Best Line: "I got forty red-white-and-blue shoestrings/And a thousand telephones that don't ring/Do you know where I can get rid of these things?"

17. Love Sick (Time Out of Mind)

If Blood on the Tracks and Desire proved Dylan didn’t get lucky in the 60s then Love Sick solidified him as a legend. It proved that he was undeniably talented as he has now managed to put out great material at three points in his life. And, Love Sick leads it all off. The opening razor-sharp notes get your attention. Dylan sings about an inner conflict which he wants to be with a woman but he’s also sick of being in love. It’s a conflicted love but not between two people, within our narrator. This is a recurring theme but now that Dylan tackles it with age it offers an alternate, more mature take.

Dylan’s late-career trilogy (Time Out of Mind, Love and Theft, and Modern Times) are all folk/rock albums but I find it hard to believe that the first is over 20 years old. I refuse to use the word timeless for these albums yet but I can’t date anything Dylan does on these albums to a period of music that has come in the last 20 years.

Best Line: I’m walking through the streets that are dead/ walking, walking with you in my head.

16. Blind Willie McTell (Infields outtake)

What do you do when you write not only a great song but one of your best? Well most would put it on that album but Bob isn't most. Dylan reflects on America's history through the view of blind blues singer Blind Willie McTell.

The simple acoustic and piano arrangement certainly seem grander than what it is until it's pointed out to you.

Best Line: I travelled through East Texas/ where many martyrs fell/ and I know no one can sing the blues like Blind Willie Mctell

15. Tombstone Blues (Highway 61 Revisited)

Some people will always be sour about Dylan’s move to rock in the mid-60s but you can’t deny that his writing as a surreal comic was only helped by the move. Dylan loves references and there’s a lot here to dig through. The first two stanza features Paul Revere’s horse, Belle Starr, and Jezebel.

To follow the cleaner production of ‘Like a Rolling Stone’ Dylan and (producer) Bob Johnston do a 180 and go for a messier and faster sound. This song was probably the furthest he got from his established folk sound but ‘Tombstone Blues’ cemented Dylan’s talent to write more than just protest songs. Dylan’s writing has never been so ridiculous yet so much fun.

Best Line: A bald wig for Jack the Ripper, who sits at the head of the chamber of commerce.

14. Positively 4th Street (single)

If this song was on Highway 61 Revisited it would be the greatest album of all-time. Instead we get one of the greatest singles of all-time. Dylan lets his anger seethe through his teeth as he confronts an estranged friend and it's satisfying to listen to because we 'get' what he's going through on this track. It's also fun to hear Dylan dis someone.

Best Line: I know the reason, that you talked behind my back./I used to be among the crowd you're in with.

13. Bob Dylan's 115th Dream (Bringing It All Back Home)

Easily Bob's funniest song. Bob is a member of a ship's crew when they discover America when they get arrested "for carrying harpoons". He manages to evade the law and he goes about trying to get his crew out of prison. He makes ridiculous orders at fancy restaurants, joins protests against himself, and crashes in other people's house only to be kicked out. However, how it ends is a cherry on top for the rest of the song.

115th Dream is one of Dylan's first reflective songs. He wasn't concerned about his social songs anymore. He became a much more reflective song writer and this was one of the first and best examples of that.

Best Line: I said you know, they refused jesus, too. He said you're not him.

12. Thunder on the Mountain (Modern Times)

I’ll be honest with you and I didn’t properly give this song a listen until compiling the list but I did fall in love with this song very quickly. His later career songs manage to pack more into less and this is a great example. If he wrote this in the 60s I feel like this could’ve been a 10-minute song but it wasn’t. Not because he wrote it in the 2000s but because it’s a song that had to be written by Dylan in his 60s. A time where he become more efficient in his songwriting.

One of the notable references in his song is to Alicia Keys in the second stanza. Apparently inspired after her performance at the Grammys but he borrowed the structure of this stanza from another song, which he did a fair bit on Modern Times. For me this reference to a figure who Dylan has had no relationship with grounds him because he still can be mystified(?) by musical figures. Alicia Keys has also been seen as a saviour of American music and so was Dylan. I think it can be seen as a nice way of Dylan wanting to move back from the spotlight so he can do his own thing and others can take his place. Now that I read this paragraph of rambling it’s probably not right but it’s a testament to how Dylan’s lyrics offer multiple assessments.

Best Line: I've been sitting down studying the art of love/I think it will fit me like a glove

11. Things Have Changed (single)

This is a bit of a cop-out but I really like how Dylan sums it up in his Oscar acceptance speech so I’ll leave it to Bob to describe it.

“I want to thank the members of the academy who were bold enough to give me this award for this song which obviously doesn’t pussyfoot around or turn a blind eye to human nature”

Best Line: I’m locked in tight, I’m out of range/ I used to care, but things have changed

10. Tangled up in Blue (Blood on the Tracks)

In Tangled up in Blue, Dylan effortlessly flows through time as recounts his experience with a past lover or maybe lovers. Each of the stanzas in the song almost acts as their stand-alone vignette. Each stanza is never clear who it’s talking about. The first two are obvious but the way Dylan uses past, present and future tense to create an oddly profound confusion. One can even assume the individual plot points in the song aren’t chronological.

Blood on the Tracks and Tangled up in Blue confirmed that Dylan wasn’t just striking lucky with his 60s output. It marked a come back for Dylan as well after a bit of slump. It also marked a new direction production wise. Dylan has a backing band but they’re not electric like this rock trilogy. Dylan’s voice is often compared to sandpaper but here isn’t angelic but he plays to his strengths. A member of his backing band pushed the song up half an octave(?) and it strains Dylan’s voice just enough to make that lingering pain within him come out.

Best Line: She said to me “don’t I know your name?”/ I muttered something under my breath/ she studied the lines on my face

9. The Times They Are A-Changin' (The Times They Are A-Changin')

This song is not only a lasting icon of the 1960s but of people's lives. This is one the few songs that Dylan purposely wrote as a "anthem for change". I don't know what hasn't be said about this song but I don think the song speaks for itself. No explanation is needed about the lyrical themes of this song. You just have to shut up and listen, which is something not enough people do these days.

Best Line: Your sons and your daughters are beyond your command

8. Sara (Desire)

Early on in the song, Dylan sings the line “So easy to look at, so hard to define”. The moment I heard it I knew Dylan was about to show me why he’s earned his Nobel Prize. But, also put me through a gut wrenching song which Dylan confesses his mistakes and his love for his wife. His pain is never talked about in the song but you know exactly what he is going through.

You can hear that this song is one of Dylan’s last attempts to save his marriage here through his voice. If Blood on the Tracks was the album about his marriage, Sara is about the devastating end.

Best Line: So easy to look at, so hard to define

7. Just Like a Woman (Blonde on Blonde)

Thanks to a 12/8 time signature, which sounds fast unless you listen carefully, every note lingers just like the past love Dylan sings of. This song manages to be both a critique of a lost love and a yearning to come back. It was obviously a complex relationship and Dylan captures the elegance, the pain and the mystique of it all.

A lot of the character in the song can be found in Dylan’s singing in which he speeds up and slows down his singing. He adds so much context to each line with his singing, which is something so few other singers can do.+In a way, I think this song can be seen as a sister song to Highway 61’s ‘Ballad of a Thin Man’.

Best Line: But when we meet again/ introduced as friends/ please don’t let on that you knew me well

6. Ballad of a Thin Man (Highway 61 Revisited)

Most people will know The Times They Are A-Changin’, Blowing in the Wind, and Like a Rolling Stone. Most people like them and it’s probably how most people get into Dylan. Except for me. I liked those songs but I didn’t start digging into his back catalogue until I heard Ballad of a Thin Man. On my second or third attempt to appreciate Highway 61 Revisited this song clicked. Then everything else fell into place. It was this song that didn’t make like him, I enamoured him.

The open piano notes get your attention and then the opening lyrics starts a fascination. The lyrics are surreal, yet somehow relatable. I didn’t realise it at first but the song is basically a big gay innuendo. Except what makes the song universal is how confusion is captured. Mr Johns, a name whose simplicity I like because it implies discreteness.

Also check out the live performance found on The Bootleg Series Vol 7: No Direction Home

Best Line: You’ve been through all of F Scott Fitzgerald’s books/ You’re very well read, it’s well known

5. Subterranean Homesick Blues (Bringing It All Back Home)

Rap’s the name of the game. Except it wasn’t in 1965 because it wasn’t even an alternative to the more mainstream music genres yet. Bob Dylan didn’t create it but his quickfire delivery certainly left an impression on lots of people. Even with all his lyrical complexities, it’s still easy to conjure up images of what Dylan is singing about. Lines like “Johnny's in basement/ mixing up medicine” carry a lot of ideas but it conveys narrative and character. It’s the show don’t tell rule.

Musically the track sounds like a sped-up country track mixed with an electric sound. This is probably Dylan’s fastest song and the 2: 21-minute length also makes it one of the shortest.

If your career is built off songs that make a statement, how do you go against everything you've been known for? You make a statement that is not what you’re expected to say. Subterranean Homesick Blues does just that.

Best Line: Orders from the D.A. look out kid/ Doesn’t matter what you did/ Walk on your tiptoes

4. Sad Eyed Lady of the Low Lands (Blonde on Blonde)

More than just a love song for his then wife, Sara. It was a wedding song. It's easily one of the best love songs ever written and its epic scope that makes it unique. Dylan takes his time singing the song, which helps account for its run time but in every pause you can feel the air and Dylan's thoughts.

His backing band were told about the structure of the song heading into recording but they never knew how long it was. For every chorus they gave it their all thinking it was the end but Dylan kept going. When you've gone all the way what can you do? Go further, obviously.

Best Line: With your silhouette when the sunlight dims/Into your eyes where the moonlight swims.

3. Like a Rolling Stone (Highway 61 Revisited)

The moment the music starts the song excites long-time listeners and grabs the attention of people who’ve never heard it before. This is all before the man who won a Nobel prize for his lyrics even starts singing. Dylan fires out a memorable line after another then comes the chorus (in which the first line rhymes with the last of the preceding stanza). If you think he can’t sing. Maybe you need to stop thinking that singing is what they make it out to be in reality TV. Dylan’s vocal performance is one of the ages as you can hear him seethe his anger through his voice. Not to much to be on a rampage but enough to bring his lyrics to life.

No matter who ranks Dylan’s songs you’re guaranteed that this song will be either be #1 or very high up. In some cases, it’s the number song of all time. More than any other song Dylan has written (maybe The Times They Are A-Changin’) ‘Like a Rolling Stone’ has become part of great American song tradition in which Dylan effortlessly contributed to in his early days.

Best Line: As you stare into the vacuum of his eyes/ And you say do you want to make a deal

2. A Hard Rain’s A-Gonna Fall (The Freewheelin’ Bob Dylan)

There are plenty of stories behind the origin of the song but in the end none matter. I mean, they do add the persona of this song but it’s the scope and haunted beauty that Dylan presents us here that matter. Part of the mystique of the song is how each song becomes more than the sum of its parts. While ‘A hard rain’ could be taken as a representation of a nuclear bomb, I think it’s when you deny this interpretation the song becomes something else.

Dylan is in a dialogue between a parent and their blue-eyed son and darling young. The things the children have felt through their experiences will have an impact on their worldviews. Through these experiences, Dylan doesn’t go for the obvious to make a protest song. He doesn’t yell at the top of his lungs in anger or become complacent. He sits in this area called ‘generous orthodoxy’. This song didn’t become the song of a generation. It changes a generation.

Best Line: I saw a newborn baby with wild wolves all around it

1. Desolation Row (Highway 61 Revisited)

Dylan's magnus opus (in my opinion) is about various characters from the bible (Cain and Abel), fiction (Ophelia, Cinderella), and some real people (Ezra Pound, Nero), in a way that he manages to capture the essence of them all with a few lines each and tieing them all to 'Desolation Row'. While the circumstances described for each character are certainly saddening, you can't help but be in awe of the songwriting. And, while each character lives a disheartening life, Dylan never denies that there is hope for these people.

Everything I like about Dylan is in this song. References that make you need to look up to understand, simple descriptions that capture characters personally, bio-imaged story and feelings, and more.

Structurally the song is a ballad but just one without a narrative direction. The song flows from one stanza to the next with great ease, which may come as a bit of a surprise as Dylan only uses about three chords. Dylan's poetical lyricism and musical simplicity is meditative unlike few songwriters can even come close to.

Best Line: Her profession’s her religion, her sin her lifelessness.

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What is your favourite Bob Dylan song?