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Bob Dylan’s five best B-sides


Lingering in the shadows of any artist’s back catalogue is the flipside world of the B-side. When it comes to Bob Dylan, he has proven so prolific in his wondrous output that the shadow he casts is perhaps the longest in music. Dylan is the sort of artist that you can accurately claim to be a huge fan of even if you have only absorbed a solid third of his discography but that shouldn’t stop you from continually digging further for there are always other gems to unearth.

There’s a slew of tracks in Dylan’s back catalogue that have inexplicably ended up on the ash heap, slung out without an album to call home, lingered on the flipside of a 45 or else as simply slipped down the back of the piano.

As Joan Baez confirmed on Desert Island Discs: “He was very creative during the short time we were together, and I was going around stealing his songs. I mean literally, ‘Four Letter Word’ he wrote, dropped behind a piano somewhere and forgot about it. I retrieved it in my own house and learnt it and a year later I was singing it and he says, ‘hey that’s a great song where did you hear that from?’ and I said, ‘You wrote it you dope!’”.

Baez’s tale is a paradigm of exactly why Dylan is the ultimate bootleg peddler. In fact, his approach to music almost makes his outtakes more defining. Here, in the sheltered world, his humble timeless tales can truly be themselves—all dust-covered and threadbare like the original vagabond himself.

Sadly, more often than not his singles were backed with album tracks making genuine B-sides a rarity as the rest of his discarded songs only made it to light on compilations. Nevertheless, we have scoured the singles and collated a collection of the five best genuine B-sides (i.e. not album tracks like ‘Gates of Eden’ that doubled up as backing for ‘Like a Rolling Stone’) that he has offered up over the course of his wayfaring career.

Bob Dylan’s five best B-sides:

5. ‘Thirsty Boots’ (Demo Version)

Record Store Day has brought about a return in the world of B-sides. Dylan gladly joined the fold and offered up a beauty backing the single ‘Wigwam’ in 2013 celebrating the event. This old demo pairs piano, acoustic and harmonica harping for a rolling ditty that recalls the blissed-out John Wesley Harding era. 

Recorded at a time when his pipes were more silken, Dylan almost croons his way through the tale of a worn-out traveller in a truly figurative sense. He sings that he is looking for “the morning in your eyes” and lines have rarely matched a melody with greater fidelity as he captures the sound of a sanguine Sunday with his stirring arrangement. 

4. ‘George Jackson’ (Acoustic Version)

Dylan’s acoustic version of ‘George Jackson’ on the B-side of the 1971 single sees his guitar work in fine form as he rattles off the folk tale of the slaying of the Black Panther leader in a timeless fashion. The big band version may well waltz along with a bit more of a skip in its stride but Dylan’s dogeared acoustic has a touch of a fitting limp as it wearily wanders by. 

On August 21st, 1971, George Jackson, was shot and killed by guards at the San Quentin Prison and while Dylan had run away from anything considered a current event at the time, he quickly returned and proved with his distant, historical sounding ditty, that society is still dealing with the same problems that they sang about in murder ballads of old. As a result, this old crooked acoustic version seems even more prescient today.

3. ‘Blind Willie McTell’ (Live Version)

This classic, first recorded in 1983, wouldn’t appear in Dylan’s discography until his 1991 Bootleg Series Volumes 1-3 with this original live version first joining the B-side realm in 2000, backing ‘Things Have Changed’. Thereafter, it has forever been regarded as a head-scratching conundrum akin to when archaeologists find ancient artefacts of phenomenal value, left in a bog in Arbroath.

This visceral unfurling musical journey in some ways tells the allegorical tale of blues itself as it follows Blind Willie McTell’s story from oppression towards the exultant boon of music. It might not be as profoundly vital as ‘Hurricane’, but it’s in the same guise of using music to give power to a story that needs to be told, and it unspools with much the same power. 

2. ‘Spanish is the Loving Tongue’ (Acoustic Version)

While the original take of ‘Spanish is the Loving Tongue’ from the album Dylan might have a hefty dose of big band pomp to savour, this humble stripped back take that accompanied the release of ‘If Not for You’ from New Morning has a note-perfect reverie to it as though this is how it was always meant to sound. The bare-bones interpretation exposes a vulnerability to the song that makes lines like the following soar: “Still I’ve always kind of missed her / since that last sad night I kissed her / I left her heart / I broke my own.”

“Soft as music” Dylan sings over a stream of half notes that seem to float by as if to prove his point. The content, in truth, bears a heavy load as he tackles love lost and moving on, but he does it with the sort of sleepy wonder that renders it almost dreamy and weightless. 

1. ‘Positively 4th Street’

In fairness, ‘Positively 4th Street’ was originally intended as an A-side and only found itself usurped by ‘Can You Please Crawl Out Your Window?’ due to an error while printing, thus fate has sealed its place on this list, and we can all be glad of it because it’s one of Dylan’s greatest songs of all time. Regardless of the printing error, this song goes to show the power of a 45. 

By modern standards, it seems incredulous that a song of this quality could go without an album to call home, but back in Dylan’s pomp, he was pumping out classic after classic for fun, and a new little seven inch from the master would have been a nice little way to spend some loose change. What’s more, the standalone nature of the song almost makes it seem like he simply, befittingly, wanted to get his great break-up rant off of his chest in a hurry. 

The beauty of the track is the juxtaposition that Dylan offered, with an unbridled disdain which he parades on a sanguine soundscape to give the impression of pure hard-earned indifference. It packs all the same punch and caustic acerbic wit as its big brother ‘Like A Rolling Stone’, riding along on a slightly sweeter organ tone. The gem in the crown of this piece of folk-rock perfection is the very last verse, perhaps one of the best break-up verses ever penned: “I wish that for just one time you could stand inside my shoes / And just for that one moment I could be you / Yes, I wish that for just one time you could stand inside my shoes / You’d know what a drag it is to see you.”