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(Photo Credit: Mike Hauptt)

From the Velvet Underground to Bob Dylan: The 11 best bootleg songs of all time

“Versace designs have always been bootlegged. Now it’s Versace bootlegging the bootleg for the bootleggers to bootleg the bootleg.” — M.I.A.

The beauty of the bootleg or rarity, and, in turn, this article with a bit of luck, 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 illumination of what the artist was working on at the time. 

The king of the bootleg is most likely 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. However, he is not alone; a great many of the tracks gathered up from the darkness in the list below will leave you scratching your head wondering why such a gem never made it onto a record to rightfully call home. 

Thus, without further ado, let’s take a look at ten of the greatest songs ever written only to be shrouded in the depths of the bootlegs, rarities and long-forgotten dust collectors realm.

The ten best bootleg songs of all time:

‘Sweet Song’ by Al Green  

Nobody, not nobody sings them like the Reverend Al Green. He is a ‘soulman’ who could sing the phonebook and whilst of course you wouldn’t listen to it unless your mind had been warped and turned abstract like the concept of love, it would nevertheless be better than just about anyone else singing it in the world. 

With that sort of voice, it’s easy to see why many of his silk-woven songs never became singles, but quite how ‘Sweet Song’ never made it off the cutting room floor is as inexplicable as a postal worker’s unwavering determination to always wear shorts. 

With a very similar sound to that which was achieved on the gorgeous Gets Next to You record, it can only be assumed that this comes out of those same 1971 sessions, but it was never heard outside of the studio until the 1990 release of You Say It! Raw! Rare! And Unreleased!. The only detraction from the wonderment of his aural spiritual syrup is a lingering confusion about how someone figured it fitting to almost ascribe this one to the ash heap of history from which it thankfully now soars like a sexy phoenix. 

‘Over You’ by the Velvet Underground

Nick Cave once said: “[Lou Reed] taught me that you can put the most sonically aggressive music and put it side by side by some of the most beautiful ballads that anyone has ever written.” As it happens, ‘Over You’ may well be one of the most beautiful songs that Lou Reed ever wrote and very few people have actually ever heard of it. 

Taken from a live recording in 1969, the band are in stirring form as Sterling Morrison delivers the sweet sort of guitar solo that brings to mind a chorus of chirping birds while Lou Reed concocts a melody of such honeyed belle that contentment is inevitable for any listener. 

Somehow, this YouTuber who uploaded it seems to have captured the tone perfectly with the sepia-toned Simpsons thumbnail that accompanies. 

‘Under This Moon’ by Nick Cave & the Bad Seeds

A common factor with bootlegs is that the tracks sequestered from the record are often variations on a theme. It would seem that ‘Under This Moon’ suffered relegation to the deep cut realm because of the similarities it shares with ‘Breathless’ on Abattoir Blues / The Lyre of Orpheus

While the beauty of ‘Breathless’ is unimpeachable, ‘Under This Moon’ is such a mammoth beast of gilded beauty that the fact it resides in the undergrowth of his back catalogue is proof that Nick Cave is one of the greatest living songwriters.

With gusto and dalliance, the track is a brisk summertime boon to behold. 

‘The Palace of the King of the Birds’ by The Beatles

In the early 1970s, a band called Klaatu caused quite an underground stir as many devoted Beatles fans thought they had uncovered the latest psychedelic guise of their recently split favourites.

Of course, it turned out to be a red herring, but what added creditability to the initial claim was how truly chameleonic The Beatles could be. 

This psychedelic jam sees them float into trippy terrain on a spring breeze of mellowed-out instrumentation. There is an awful lot of joy to sponged from this gentle shimmering Let It Be session track. It’s the sort of effervescing melody that you could listen to all day. 

‘You Ain’t Goin’ Nowhere’ by Bob Dylan

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

‘Conversation Piece’ by David Bowie

A posthumous boxset release of the same name brought a slew of long-forgotten Bowie songs back to life in 2019 and chief among them was the folky gem that is ‘Conversation Piece’.

Bowie may have struggled to find any sort of fame or acclaim during his fallow early spell but tracks like this show that he was always a burgeoning talent. 

Not a great deal is known about this track even now. There are drums, a cello and what sounds like an oboe in the mix, but the players remain uncredited. If anything, the obfuscated origins of the hidden song add another layer of mystique to the twelve-string beauty of Bowie’s unfurling poetry.

‘White Tornado’ by R.E.M.

On the liner notes for their Dead Letter Office compilation album, Peter Buck writes: “We wrote this song the same afternoon we wrote ‘Radio Free Europe’, I think. This is an unreleased version recorded at Mitch Easter’s Drive-In Studio at the same time as our first single on Hibtone.”

With that sort of competition, it perhaps isn’t all that surprising that the track resided on the subs bench, however, that is more of a reflection on a truly prolific creative explosion as opposed to a lack of class on the part of ‘White Tornado’.

The song has the joyous youthful feel that all surf songs should. In less than two minutes it could rattle clouds from the sky and thrust a beer kindly forward. 

‘In the Hot Hot Rays’ by Fleet Foxes

Before Fleet Foxes turned towards harmonies and exploded as beanie-clad saviours of folk onto the world stage, they were putting out chilled out folk-rock to behold.

The First Collection compilation record that they unleased in 2018 resurrected their early rousing efforts and there is a slew of rousing classics among them. 

With a mellowed-out earworm of a riff and Robin Pecknold’s measured vocals, ‘In the Hot Hot Rays’ is a nostalgia-inducing indie classic that sprinkles a sanguine aural air to any summers day. 

‘Roses are Blooming’ by Harry Nilsson

Capturing Harry Nilsson performing live at any point in his career is a rarity, and it is not for a lack of ability to be able to do so. Nilsson was, in fact, one of the greatest pop singers of all time, but crippling anxiety prevented him from taking to the stage all that often.

The profound tragedy to this sad twist of fate is that he cleared soared on the joy of performing live on the rare occasion that he did end up doing it. The record Campaign Hero collates his appearances on both the Skip Wehner Show and The Smothers Brothers, all of which are scintillatingly good. This track, in particular, sees him stretch his octaves with the ease of a blackbird and briskly deliver a short and sweet gem on the breeze. 

‘Machine Gun’ by Jimi Hendrix

Too many people lament the quality of modern music without ever really exploring the depth of unbelievable talent that is actually out there. However, if there is one undeniable element creeping into the mix of current records it is that all too often songs have a distinctly manufactured feel about them and lack any live bravura. 

Jimi Hendrix, on the other hand, was an artist whose records always sounded like they were recorded on stage let alone live in a studio. Hendrix was not only a guitar god but a performative hero at that.

The marginal drawback to that was that he could often wail a little too long and loosely for a philistine in it for the jams. This live deep cut, however, sees him dole out a perfectly refined piece of pure energy and atmosphere. And it even delightfully underscored one of the best Coen Brothers scenes ever, to boot. 

‘I’ll Try Anything Once’ by The Strokes

Sometimes a deep cut trumps the latter permutation that follows, ‘You Only Live Once’ is a fantastic single from The Strokes, but there are similar indie-rock classics lingering in their records that are more than capable of conquering it. The original demo, however, is a wonder to behold.

‘I’ll Try Anything Once’ defines the inherent appeal of deep cuts in general. It stands out as a far more withdrawn and vulnerable song than the fresh indie joys that make it to record. With Nick Valensi tentatively tapping about a sort of mellowed melancholic melody on piano and Julian Casablancas purring out the best lyrics that he has ever written, the song almost seems fated to be shrouded in the ethereal darkness of demos where creativity quietly creeps into illuminated existence.

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