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From Prince to Bob Dylan: The 10 most essential bootleg albums of all time

The idea of a “bootleg recording” is a concept lost to time. Back in ye olden days of the music industry, when the distribution of music was most assuredly not at the touch of a button, performances and recordings that were not officially released by record companies could still find their way to record stores and secondary markets through entrepreneurial minds with access to a vinyl presser. It might seem strange in the era of YouTube and Soundcloud, not to mention how extremely common it is for artists and labels to scrounge up every last recorded note for a box set releases nowadays, but the unrefined, unfinished, or unverified pieces of music that came through bootlegs were controversial enough to incite slight hysteria among label heads who believed their product was being diluted by knockoffs and cheap profiteers looking to make a quick buck.

The reaction of artists to bootlegging has varied: bands like Led Zeppelin – and more specifically manager and intimidator extraordinaire Peter Grant- attempted to find those responsible and shake them down for stealing the band’s material. In contrast, the Grateful Dead famously welcomed recorders at their live shows by setting up a specific section near the soundboard to optimise the quality of these bootleg recordings, and the subsequent tapes that were passed from Deadhead to Deadhead increased the band’s profile exponentially.

If you’re looking for a primer to understand the wild world of bootlegging, look no further. Here are 10 of the most important, and most essential, bootleg recordings in rock and roll history.

The 10 greatest bootleg recordings of all time:

Bob Dylan: Great White Wonder

This is where it all starts with bootlegging. Not literally, as movie soundtracks and live performances of popular music artists had been circulating in the marketplace for years, but this was the first bootleg to see major cultural attention and distribution.

Mainly consisting of outtakes and informal sessions that would later be compiled into Dylan’s 1975 album The Basement Tapes, the sound quality of the songs on Great White Wonder is notably shoddy, especially on the material that Dylan recorded in a Minnesota hotel room back in 1961. Still, Great White Wonder was a watershed moment in the world of bootlegs, having been the first release from the notorious label Trademark of Quality, which churned out some of the most notable bootlegs of the ’70s. It also served as the impetus for Dylan to recognise the incredibly high demand for his unreleased work, eventually leading to his famous The Bootleg Series that began to legitimise (and allow artists themselves to profit off of) the unpolished and unrefined works that had been circulating for decades.

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The Rolling Stones: Live’r Than You’ll Ever Be

Here we see one of the first examples of bootleg recordings becoming so popular that the artist themselves had to respond. On 9 November 1969, The Rolling Stones performed at the Oakland Coliseum in California and played a number of their most recent cuts, including ‘Gimme Shelter’, ‘Midnight Rambler’, and ‘Honky Tonk Woman’.

In the crowd that night was “Dub” Taylor, the founder of Trademark of Quality, who snuck in a microphone and reel-to-reel tape recorder to document the proceedings. The result, Live’r Than You’ll Ever Be, wound up being reviewed by Rolling Stone and eventually received a gold certification from the RIAA. The Stones were apparently so caught off guard at its success that their subsequent live album Get Yer Ya-Ya’s Out! was allegedly spearheaded to counteract how widespread the distribution of Live’r Than You’ll Ever Be had gotten.

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The Troggs: The Troggs Tapes

1970 was still a fairly delicate time in popular music. You couldn’t exactly get away with profanity, and most bands worked hard to retain a certain kind of squeaky clean image. So imagine the capital-s shock that must have been felt by putting on a bootleg tape that featured members of The Troggs arguing with palpable vitriol and seemingly disintegrating right in front of your ears.

The band were trying to cut a single, ironically titled ‘Tranquility’, and the pressure they felt as their glory years waned is felt in every last insult and shouting match inadvertently captured on tape. If you are sensitive to certain four-letter F words, I would not recommend The Troggs Tape. For anyone else, I highly recommend The Troggs Tape.

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Pink Floyd: Dark Side of the Moo

If you were an American fan of Pink Floyd in the ’70s, your collection of the band’s material was frustratingly incomplete compared to that of English record buyers. Due to the ramshackle practices of EMI distributing some of their most famous artists’ records to a number of different labels in the U.S., the results would often be truncated, sliced up, and generally not representative of what the artists originally planned.

To rectify those injustices comes Dark Side of the Moo, which compiled tracks like ‘Astronomy Domine’ and ‘Point Me at the Sky’ for the first time on U.S. soil. Bands like The Beatles had required their material to be unaltered by labels as early as 1967, but it took bootlegs like Dark Side of the Moo to finally convince labels to keep their track listings consistent.

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The Yardbirds: Golden Eggs

Trademark of Quality were the undisputed kings of bootleg recordings in the 1970s, releasing material from a range of artists in the rock world like David Bowie and Santana that mainly consisted of live tracks or studio outtakes. Occasionally though, the label would venture into the compilation game, mainly to cover our-of-print material from British artists not readily available to American audiences.

In 1975, during the height of Led Zeppelin’s popularity, the label released Golden Eggs from Jimmy Page’s previous outfit The Yardbirds featuring much of Page’s guitar work during his tenure in the band, along with occasional features from Eric Clapton and Jeff Beck. These recordings helped solidify the Yardbirds’ reputation as a farm system for some of the most talented guitarists of all time and bolstered the band’s legacy a number of years after having closed up shop.

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Elvis Presley: Elvis’ Greatest Shit

To understand the world of bootlegs is to appreciate both sides of unreleased material. A number of recordings could be viewed with a sort of Robin Hood-esque grandeur: hidden gems squired away by greedy record companies valiantly bestowed onto the public through less than legal means. But then there are the recordings that were never released for a reason.

Everything about Elvis’ Greatest Shit is in bad taste, from the album’s title to the front cover showing a deceased Presley at his actual funeral to the LP’s contents, largely consisting of film soundtrack songs that not even Elvis fanatics would deem up to snuff. Elvis’ Greatest Shit isn’t exactly a pleasant listening experience, but it’s an important line of demarcation in the history of bootlegging because it shows why some unreleased material is unreleased in the first place.

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Frank Zappa: Mystery Box

A massive stash of unreleased concert recordings and television appearances, Mystery Box is ten vinyl LP’s of solid gold for any Frank Zappa fanatic that covers the entirety of his golden age in the late 1960s to the late ’70s.

Unfortunately Frank wasn’t a fan of the unauthorized recordings, so he came up with the simplest solution: since the bootleg did most of the work for him, all he had to do was repackage it with minimal changes and distribute it officially. The not-at-all subtle title of this compilation? Beat the Boots! Wonderfully petty, that Mr. Zappa was.

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Prince: The Black Album

You knew what you were getting into when you listened to a bootleg: unmastered, rough demo recordings or crudely mixed live tracks were the norm. If an album was fully fleshed out, professionally recorded studio work, why not just release it legally? No one would just waste perfectly good material like that, right? Enter Prince.

In 1987, the Purple One records a funky, hard-hitting album meant to contrast the widely varying styles on Sign ‘o’ the Times. But after a “spiritual epiphany” (or bad drug trip) Prince becomes convinced that the album contains malevolent entities and shelves it less than a month before its release. Promotional copies had already been sent out, so it doesn’t take long for the album to be bootlegged into oblivion. Eventually, Warner Bros. releases The Black Album officially, even offering free copies to those who sent their bootleg copies into the record company. At that point, most owners realised they had gold on their hands, and the bootlegs have become far more valuable than the legal version even though they contain the same music.

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Oasis: Wibbling Rivalry

There is some argument as to whether this actually counts as a bootleg. First off, it’s only the length of a conventional single, not a full length album. Secondly, it was distributed by Fierce Panda Records, a fairly well respected independent label that has released official material from the likes of Coldplay and Death Cab for Cutie. Third, it’s not a song, it’s an interview with the brothers Gallagher where they verbally spar over a now-famous drunken incident on a ferry.

Still, it’s hard not to appreciate the magnitude of Wibbling Rivalry in terms of scrounged up, not explicitly meant for release-type of recordings. It reached number 52 on the UK singles chart, firmly established the Gallagher’s warring dynamic, and reopened the door for band scrums like The Troggs Tape to reignite the seedy world of bootlegs for a mass audience.

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Danger Mouse: The Grey Album

As unauthorised sampling became much more common in the ’80s, and as unofficial recordings became commonplace on YouTube in the new millennium, the age of bootlegs is now officially over. But there was one last hurrah for the practice before the internet took over: Danger Mouse’s The Grey Album.

Combining vocals from Jay-Z’s The Black Album with instrumentals and samples from The Beatles’ White Album, The Grey Album was simply ahead of its time when it appeared in 2004. EMI, apparently not having learned their lesson from headaches of the bootlegging past, attempted to halt its release, only serving to give it an increased platform a-la The Streisand Effect. Now that mashup albums proliferate freely on online platforms, The Grey Album exists as the transition point between the Wild West days of bootlegging and the ubiquitous remix culture that we live in today.

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