Credit: CBC

The beauty of any bootleg is that they can creep out from the shadows of your favourite artists back catalogues as a brand-new song, just like a birthday gift that got lost in the post. What’s more, when you open the package, it reveals something new, offering just a little more illuminating light through the workings of an artist’s creative process.

The king of the bootleg is most definitely Bob Dylan who had a spell so prolific that half of the songs he wrote he would simply leave lying around and forget about them — and that’s not in a figurative sense either, as Joan Baez affirmed 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!’”

His works imply extreme care in his creativity, as Paul Simon once said about how Dylan surely sweated over every line: “With Dylan, everything he sings has two meanings. He’s telling you the truth and making fun at the same time.”

However, clearly, that same care wasn’t stretched to thoughts of how they would be released, thus, lord knows how many classics of his lay dormant in a cubbyhole or await the pandora’s box moment of a dropped stylus to finally burst their forgotten sound into bloom. Alas, below we are looking at simply ten of them that prove essential for any Dylan fan to unearth. 

Ten essential Bob Dylan bootlegs:

‘You Ain’t Goin’ Nowhere’ – Studio Outtake 1971

There is so much depth to Bob Dylan’s work that quite often one key factor is chronically overlooked: how good he is at writing a simple jam. Away from all of his spiritual introspection, inciteful views on society and philosophy and his filigreed poetic propagation is an uncanny knack of tying a few chords together into a simple pleasant melody that goes almost as unrivalled as it is unnoticed.

This particular rhythmic gem was first written by Bob Dylan during his self-imposed 1967 exile from the music industry following mounting stresses and a near-mythic motorbike accident. He performed this rough cut with The Band and then it was condemned to the backburner until 1971’s Greatest Hits Vol. II.

‘You’re a Big Girl Now’ – Take 2

Taken from Dylan’s More Blood, More Tracks release back in 2018, Dylan revealed an early stripped back take of ‘You’re a Big Girl Now’ that provided a tender counterpoint to the often-caustic Blood on the Tracks masterpiece.

The song also does what many bootlegs do brilliantly, it removes any performative notion to the song and lays it down with a vulnerable bare-bones profundity. There is no hint of final take pressure and bravura, it’s just Dylan quietly acquainting himself with the track and it proves to be one hell of a thing to behold.

‘Abandoned Love’ – Studio Outtake 1975

Although ‘Abandoned Love’ was recorded in 1975, it wasn’t released until 1985 on his Biography bootlegs LP. The track was dropped in favour of ‘Joey’ from the Desire sessions. However, it more closely resembles his pining ode on ‘Sara’ in its documentation of love gone awry.

With flowing Rolling Thunder Revue sounds and lyrics of paradoxical tender torture, Dylan perfectly captures the sore malaise of a breakup with sonic perfection. While there is no doubting the brilliance of Desire, ‘Abandoned Love’ certainly wouldn’t have gone amiss. 

‘Tomorrow is a Long Time’ – Live at Town Hall, New York, April 1963

Upon the ten-year anniversary of Elvis Presley’s death in 1987, Bob Dylan told US magazine: “When I first heard Elvis’ voice, I just knew that I wasn’t going to work for anybody; and nobody was going to be my boss. He is the deity supreme of rock ‘n’ roll religion as it exists in today’s form. Hearing him for the first time was like busting out of jail,” he said, before concluding: “I think for a long time that freedom to me was Elvis singing ‘Blue Moon of Kentucky’. I thank God for Elvis.”

This notion of your childhood hero suddenly channelling your whims is what Bob Dylan had in mind when Rolling Stone asked him if there were any particular artists that he liked to see take on his songs. “Yeah, Elvis Presley,” Dylan replied. “I liked Elvis Presley. Elvis Presley recorded a song of mine. That’s the one recording I treasure the most…it was called ‘Tomorrow Is A Long Time’. I wrote it but never recorded it.”

Indeed, Dylan did write it back in 1962, and it demonstrates an absolutely terrifying amount of wisdom for someone so young at that time, not to mention the sheer unadulterated beauty of the behemoth thing.

‘House of the Rising Sun’

There are certain folk songs with an almost eerie timelessness about them, as though they hark back through eternities and dip a toe into the streaming future. That is how Bob Dylan once saw the old folk songs that inspired him. In 1961, he was stirred by the old Dust Bowl singers like Woody Guthrie to leave university and walk the roads to Greenwich Village like Jack Kerouac and his beat disciples had done before him. 

Therein there was somehow so many folk singers crammed into one borough that it’s hard to understand just how it sustained itself. There were quite literally a thousand gingham-clad troubadours, all quite literally singing the same songs, and all suffering the same downbeat tropes of the genre which led Dylan towards individualistic introspection.

This transition to introspective songwriting meant that the folk songs of old were put on the back burner, including the classic ‘House of the Rising Sun’. Ultimately, Dylan only played the classic song live eight times, and only twice in the ’60s. It is believed that this rare recording took place either on April 12 or April 18, 1963; although the exact date is disputed. It sees Dylan play in lend it a fingerpicking style and he imbues it with a befitting careworn atmosphere, for a folk combination that just seems right. 

‘I Want You’ – Studio Outtake

There is a monumental undertone to hearing Dylan’s first immortalising of a song in acetate, and when it’s a Blonde on Blonde classic, that moment of ether coaxing alchemy is elevate to strangely spiritual heights. In subsequent years, the song has gone down as a classic, but for my money, it has never sounded as good as this first time. 

This version of the song, the first take that Dylan and the band laid down, is much rockier with a sweetly sustaining organ sound. As well as providing the first take of the track we also have Dylan providing a quick rehearsal of the song. Recorded in the early hours of a March morning in 1966, a 24-year-old Bob Dylan steps up to the mic to record a purring sultry classic. “‘I Want You’,” he responds when asked to name the track, and the rest, as they say, is ancient history.

‘Blind Willie McTell’

This classic, first recorded in 1983, wouldn’t appear in Dylan’s discography until his 1991 Bootleg Series Volumes 1-3. 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.

‘The Groom’s Still Waiting at the Altar’

Dylan’s switch towards up-tempo blues-rock in the late 1970s and early 1980s might have raised a few eyebrows, but it certainly reaffirmed him as the original propagator of the mantra that David Bowie would give voice to when he remarked: “Never play to the gallery. Always remember that the reason you initially started working was that there was something inside yourself that you felt that if you could manifest it in some way, you would understand more about yourself and how you coexist with the rest of society.”

This rousing number rattles the rafters in a way that some of the songs only stretched for during this era and as such came off as misfires. From the slide-guitar that has slipped off the radar into an off-road territory to his own impassioned snarl, there is an energy on display here akin to Highway 61 Revisited, rendering it one of the best of a subpar era for Dylan.

‘I Shall Be Released’

‘I Shall Be Released’ is the sort of protest song that got passed around the houses so much that there’ll be fans out there who perhaps don’t even realise that Dylan wrote it in the first place. Although the likes of Joe Cocker and Nina Simone might have lent it their own incomparable vocals and Dylan’s pals in The Band may well have delivered the definitive version, there’s certainly a beauty to the raw original that is hard to surpass.

Taken from The Basement Tapes Raw, Dylan really gets the simple point of the song across in uncomplicated tones. The recording even has the sense that he is providing the mandate for others to follow when he performs it, rather than polishing up the fineries and labelling his work with a signature of his own.

‘Kansas City’ by The New Basement Tapes

Whether this can be classed as a Bob Dylan bootleg is debatable, but it’s certainly worth an honourable mention. Using unearthed handwritten lyrics and melodies The New Basement Tapes rehashed scraps of Dylan’s source material into ensemble pieces of music, all helmed by the sui generis sonic force that is T Bone Burnett. This particular single sees Johnny Deep, Jim James, Marcus Mumford, Rhiannon Giddens, Taylor Goldsmith and Elvis Costello all join forces.

Burnett would later give The Daily Telegraph his interpretation of the track, stating: “In 1967, he had gone, in five years, from being an obscure folk singer to an international rock ‘n’ roll icon of the highest magnitude. And, in the process, his original supporters turned on him and it seems like he’s saying: ‘Just how long can I keep singing the same old song?’.”

Adding: “There’s a great line: ‘You invite me into your house, then you say you got to pay for what you break.’ I think that resonated very strongly with Marcus, because he has had a similar trajectory,” Burnett added. “He came out of the box very strong, became internationally successful and suffered an extreme backlash. Kansas City is his song as well.”