19 favourite Bob Dylan songs

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Well, it’s summertime, the Olympic Games are in full flood, and my mind is on holiday. So I can only set aside the usual sort of cod-philosophical post for the time being, and instead revert to lists. Maybe a series of lists. I’ve not produced any lists for ages, and they’re easy (or so it seems), and sometimes interesting, and of course vitally important.

To kick things off, here are my nineteen favourite Bob Dylan songs. Not the nineteen best, which as ever is a nonsense game to play, but nineteen for which I feel a special affection after some forty-five years of listening to the man. I’ve restricted them to one per album, though they more or less turned out that way in any case. And, in case you’re asking, I’ve never much cared for Blonde on Blonde. So, in reverse order…

19. In Search of Little Sadie (Self Portrait)

Some of my favourite Dylan songs weren’t written by Dylan, but he puts such a stamp on them that they become his. This was originally a folk song from the 1920s about a man who shoots his girlfriend and is sentenced to prison for him. Dylan adapted it from Clarence Ashley’s 1930 recording and turns it into a kooky ballad with weird chord changes and shifts in tempo that ends up sounding like a deconstruction of itself.

18. Tempest (Tempest)

Dylan’s longest song yet (a shade under 14 minutes) and one of his most satisfying epics. Its inspiration comes out of The Carter Family’s folk song ‘The Titanic’ mashed up with a viewing of James Cameron’s film. Dylan adds observations both banal and mysterious, the overall theme of looming disaster one that dominates the brilliant Tempest, his most recent – and maybe last – album of original music.

17. Sugar Baby (Love and Theft)

It’s hard to pick one song from Love and Theft, an album where each of its constituent parts in particularly enriched by association with the others. But ‘Sugar Baby’, with its faint echo of the death-rattle blues of Dock Boggs, is the track that haunts me the most, with its distinctive combination of menace (that treading beat) and mournfulness (that falling chord progression). A song of well-earned world-weariness.

16. Rita May (Masterpieces)

This was recorded during the Desire sessions, was released as a the B-side of a single and ended up on an obscure compilation album. it’s the kind of throwaway song of his that’s always appealed to me, a dash of fun amid the more heavily considered pieces. This is a chirpy number with goofy lyrics (“Rita May, Rita May / You got your body in the way”), with spare yet tip-top musical accompaniment (exuberant violin from Scarlet Riviera, Howard Wyeth’s pin-sharp drumming). Sadly, it’s not on Spotify.

15. One More Night (Nashville Skyline)

Possibly the cheesiest song Dylan has ever recorded, but it makes me smile every time I hear it. It maybe the closest he’s got to being like one of his lifelong heroes, Hank Williams. It’s a pure song.

14. Freight Train Blues (Bob Dylan)

The first Dylan album still sounds like one his best. Barely out of his teens yet trying to sound like a 1930s Delta bluesman, he gets away with it through sheer exuberance and belief. ‘Freight Train Blues’, adapted out of Roy Acuff’s version of a John Lair country song, Dylan’s frenetic train sounds like the brake handle has fallen off. It’s a song from someone who doesn’t know much yet but knows he can do anything.

13. When the Ship Comes In (The Times They Are A-Changin’)

Somewhat overlooked among the heavyweight folk songs of Dylan’s early period, this ballad of impending retribution sounds like it could have come from any century yet is absolutely of its moment.

12. New Pony (Street-Legal)

Dylan doesn’t do raunchy, and probably with good reason, but this thumping single entendre piece from the overlooked Street-Legal album is a shining exception. He never used backing singers so well as he does here (“How much, how much, how much longer?”).

11. Sante Fe (The Basement Tapes Complete & Bootleg Series Vols. 1-3)

Another throwaway gem. Of all of the songs recently unearthed from the complete ‘Basement Tapes’ session, this wistful yet hopeful number is the one that keeps drawing me back the most. It’s not entirely clear what the muffled lyrics are about, but it hardly matters. It’s a wanderer’s song, the calling card of someone forever on the road to somewhere else, and not minding.

10. Lily, Rosemary and the Jack of Hearts (Blood on the Tracks)

What I think I like best about this song if how it’s been talked about as the possible narrative source for a film, yet no one has made the idea work because it isn’t quite possible to determine what the story is. The elements appear to be there, but what seems real slips into dream and metaphor. It’s the film that you remember rather than the film that you saw. It’s also bright, funny and catchy, an inspired counterpoint to the tales of love just lost that fill Blood on the Tracks.

9. Not Dark Yet (Time Out of Mind)

The shock effect of Time out of Mind, after the lean years of the 80s and 90s, has lessened a little, because of the still finer albums that followed it, but this song of resignation at the nearness of death (“It’s not dark yet / But it’s getting there”) still takes the breath away. It’s the simple guitar figure, like the tolling of a bell, that makes it. Probably the first rock song written about getting old, and as such maybe one of his most influential.

8. Workingman’s Blues # 2 (Modern Times)

The older Dylan gets the more you understand his songs are a commentary on what he had heard. This is a sort of sequel to Merle Haggard’s ‘Working Man Blues’, which mixes the personal with the political in a profoundly mysterious way. Has Dylan ever come up with a better few opening lines than here? “There’s an evenin’ haze settlin’ over the town / Starlight by the edge of the creek / The buyin’ power of the proletariat’s gone down / Money’s gettin’ shallow and weak”. It feels like the key to a failing America.

7. Drifter’s Escape (John Wesley Harding)

A drifter is taken from a courtroom, unable to understand what it is that he has done wrong. “You fail to understand,” says the judge, “Why must you even try?”. But just at the point when the world has condemned him simply for being, a blot of lightning strikes, all kneel to pray, and the drifter escapes. It’s Kafka with a get-out clause.

6. Lone Pilgrim (World Gone Wrong)

Dylan was discovered by John Hammond, the music producer who did so much to recover American folk song, and Dylan has been following along the same path ever since. He recovered this transcendent 19th century folk hymn from a 1960s Doc Watson recording, using it to conclude his album of covers, World Gone Wrong, a pivotal record in his career. A song set at a graveside, it’s about resignation, compassion and salvation. Perhaps his single finest musical performance.

5. Never Say Goodbye (Planet Waves)

I’ve never understood why this poetic gem isn’t better known, and certainly more revered than appears to be the case. A haunting picture of wintertime (“Twilight on the frozen lake / A north wind about to break / On footprints in the snow / Silence down below”) rises into a rhapsodic declaration of mystical love as music and words spiral upwards. One from the heart.

4. Red River Shore (Tell Tale Signs)

The ‘Bootleg’ series of albums has consistently dumbfounded with examples of songs rejected by Dylan around which anyone else would have built an entire career. Most dumbfounding of all is this song, left off Time Out of Mind, probably because it didn’t match the mood of the rest of the album. It’s an adaptation of a traditional song about a lost love, which Dylan converts into ballad both simple yet with the weight of life on its shoulders. “Some of us turn off the lights and we live / With the moonlight shooting by / Some of us scare ourselves to death in the dark / To be where the angels fly”. Plus it has the prettiest accompaniment, and a pay-off in the final verse like no other.

3. Love Minus Zero / No Limit (Bringing It All Back Home)

The genius of simplicity. A mid-tempo number without chorus, underpinned by simple but insistent strummed chords that prefigure the Velvet Underground, overlaid with a lyric about a mysterious, superior woman (dated now, but it was the 1960s). It’s the confidence that it exudes that I find so impressive. Like its subject, it just knows more than others do. Here Dylan leaves the competition so far behind, he’s in a contest all of his own.

2. Queen Jane Approximately (Highway 61 Revisited)

Of all the songs on the album many think is Dylan’s best, this track tends to get the least attention – so naturally it’s my favourite among them. It’s a song not quite like any other, with verses that sound like you’ve stumbled in the middle of them, a lyric that poses questions without answers, and a rising and a falling tune that surges forward on some neverending quest. The accompaniment is a bit of a racket, and not entirely in tune, but somehow it only adds to the charm. It’s a song that just sweeps me away every time I hear it.

1. Corrina Corrina (The Freewheelin’ Bob Dylan)

There was an old pop song called ‘Corrina Corrine’, but Dylan turned it into his own. Why is this my favourite of all his songs? It’s perfectly formed, and it lightly touches the heart. It just satisfies.

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2 thoughts on “19 favourite Bob Dylan songs

    1. I’m temperamentally driven to pick the minor or the overlooked, but all are something quite special. I’m intrigued how many are adaptations of other people’s songs. Maybe the greatest role he has played is as interpreter.

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