Record labels hated them. (So did Neil Young.) Fans loved them. (So did the Stones.) Bootleg records played an important, though ambiguous, role in the music world during the rock era. (You can find The A.V. Club’s history of bootlegging here.) On one hand, they were technically illegal, the people who made them didn’t share their profits with artists, and they frequently contained material that musicians didn’t want released to the public. On the other hand, they provided fans with a perspective into the creative process that was unique in pre-social-media days, introduced a number of formats (live albums, odds-and-sods collections, box sets) that legitimate labels would make a lot of money from, and basically kept rock ’n’ roll’s renegade spirit alive during its most bloated, out-of-touch days. With their backdoor production quality, they often didn’t seem like much, but a handful of them have turned out to have a legacy that few people—especially the ones making them—could have predicted. Below are a few of the best and most important.

1. Anthology Of American Folk Music (1952)

For a musical community so fixated on authenticity, the postwar New York folk scene had some fairly illegitimate roots. The whole thing was essentially tied together by the Anthology Of American Folk Music, a six-LP compilation of pre-Depression 78s (curated by the experimental filmmaker, amateur ethnomusicologist, obsessive collector, and proto-hippie Harry Smith) that connected the young, white, urban bohemians of the scene with obscure, decades-old cuts originally marketed as “hillbilly” and “race” music. And though it was released through the venerable Folkways label, no one bothered to clear the rights for the recordings until the set was reissued in 1997. Smith not only saved a valuable trove of early American music and provided inspiration for one of the century’s most important aesthetic movements, he also set the precedent for unruly offspring like the garage- and punk-centric Pebbles and Killed By Death compilation series that ignored legal niceties for the sake of keeping obscure sounds alive. [Miles Raymer]

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2. Bob Dylan, Great White Wonder (1969)

The bootleg record industry as we know it was born in 1969 when two enterprising hippies named Ken Douglas and Dub Taylor decided to use their music-biz connections to press up vinyl copies of a tape of Dylan rarities. A hodgepodge of then-unreleased Basement Tapes material recorded with The Band, a pre-fame demo tape recorded in a Minneapolis apartment, and a live performance on The Johnny Cash Show, it was still an immediate hit in L.A.’s counterculture-friendly record shops and on the city’s more daring rock radio stations. Packaged in a plain white sleeve, the LP became known among fans as Great White Wonder. Its success inspired Douglas and Taylor to pursue careers as renegade record moguls with their legendary bootleg label Trademark Of Quality, and a legion of copycats to follow their lead (often with their own pressings of GWW). [Miles Raymer]

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3. Bob Dylan and The Band, The Basement Tapes (1967)

As Dylan helped to get the bootleg industry off the ground in the first place, so would he also play a substantial role in keeping it going thanks to his baffling decision in 1967 to retire from the pop-star business and start a brief new career as an anonymous songwriter for other artists. He and The Band cut acetates of some of the tracks they’d recorded in casual basement jams in order to shop them around, and they ended up in the hands of critics who loudly campaigned to get the album officially released. Columbia eventually came through, kind of, with a sloppily assembled LP padded out with Dylan-less Band songs, but there was plenty more material left over for bootleggers to continue reissuing their own editions. (Dylan eventually got the last laugh in 2014 when he released a six-disc, 139-song Basement Tapes that included tracks even the bootleggers hadn’t heard before.) Over the years the bootleg versions became something like holy relics in the rock underground, and Dylan and The Band’s ramshackle sessions would play a formative role in the birth of alt-country and indie rock. [Miles Raymer]

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4. Bruce Springsteen, Roxy Night (1978)

Bruce Springsteen has a well-earned reputation for being one of the greatest live performing acts in the history of rock music. But he may have hit his peak in 1978 with the Darkness On The Edge Of Town tour. While many cite the Boss’ show at the Agora in Cleveland or the Winterland in San Francisco, this gig at the Roxy Theatre in Los Angeles might just edge both of those out as the high-water mark of the tour. Taken from an FM radio broadcast, audio recordings of this show have circulated around the bootleg network for years, sometimes even with the deejay introduction and patter included. Even almost 40 years removed, the intensity is palpable through a pair of headphones. [Corbin Reiff]

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5. The Rolling Stones, Brussels Affair (1973)

The Stones often billed themselves as “the world’s greatest rock ’n’ roll band,” and their live performances went a long way toward backing that claim up. So it’s not surprising that they were the first band to have a concert bootlegged, when Dub Taylor somehow managed to sneak a microphone and reel-to-reel tape recorder into a show at the Oakland County Coliseum and pressed it up as Live’r Than You’ll Ever Be. (Mick Jagger and Keith Richards were reportedly thrilled over its release.) Recorded four years later at a concert in Belgium—which the band put on because France wouldn’t let them in—The Brussels Affair captured the Stones at the absolute peak of their powers, savagely and expertly thrashing their way through two unhinged sets of prime ’70s material. Stones connoisseurs have long considered it their best live recording. The band apparently agrees, since they released an edited-down official version in 2011. [Miles Raymer]

6. Neil Young, Chrome Dreams (1976)

Neil Young is a mercurial, prolific, and inscrutable musical force, and over the years he’s walked away from a number of finished albums, or made drastic changes to them, for reasons that even he can’t adequately explain. In 1977 he finished an album he called Chrome Dreams, inspired by a drawing by his longtime producer David Briggs. The material pulls together all the disparate strands of Young’s musical identity—the squalling guitar hero, the country rocker, the intensely intimate acoustic balladeer—in a balance that only a couple of his albums have ever been able to do. If it had been released, it would easily rank near the top of his best recordings. Instead he canceled production and made the far inferior American Stars ’N Bars, which mixed alternate versions of a few Chrome Dreams cuts in with some of his most unremarkable material of the decade. Luckily an acetate of the scrapped album made it into the hands of bootleggers, a fate that his Homegrown album and the almost mythological first mix of Tonight’s The Night unfortunately didn’t meet. [Miles Raymer]

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7. Led Zeppelin, The Final Option (1983)

Bootleggers loved Led Zeppelin for its legendary live shows and massive popularity among the kind of intensely devoted music fan who’d gladly plunk down money on recordings of dodgy provenance. With its tendency in concerts to stretch its songs out into jams long enough to fit an LP side, Led Zeppelin was particularly suited for box sets. In the mid-’80s, the Rock Solid label made a name for itself with extravagant sets aimed at the most obsessive collectors, including a 20-disc Dylan collection and three separate 10-disc Frank Zappa boxes. But no box set before or since can compare in sheer ridiculousness with The Final Option, which reached new levels of audacity with 70 LPs of Zeppelin recordings packaged in custom-made acrylic cases adorned with the band’s signature runes. In terms of unrestrained bombast, it truly is the Led Zeppelin of box sets. [Miles Raymer]

8. The Velvet Underground, Live At The Gymnasium (1968)

The Velvet Underground is one of those bands whose earliest years are shrouded in fable and enhanced by legend. This recording of a gig the band played on April 30, 1967 in New York goes a long way to enhancing both elements and captures a portrait of the group at its most incendiary. The guitars are cranked, the drums are raucous, and you can almost hear Lou Reed’s vocal cords tearing out of his throat. It’s pre-proto punk. The entire show was eventually released as part of the deluxe 45th anniversary edition of the band’s White Light/White Heat. [Corbin Reiff]

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9. The Beatles, A/B Road (2004)

There’s extensive and then there’s the A/B Road bootleg set. Amassed on a staggering 83 CDs, the collection captures nearly every note, every cough, every slight, every joke, and every conversation The Beatles committed to tape during the tumultuous Get Back/Let It Be sessions in 1969. If it seems excessive, it most definitely is, but then again, The Beatles are renowned for having one of the most ardent and dedicated fan bases in music history, and there are apparently plenty of folks out there willing to sort through hours and hours of musical and non-musical moments to try and make sense of the band’s creative process. [Corbin Reiff]

10. John Lennon, Paul McCartney, Stevie Wonder, and Harry Nilsson, A Toot And A Snore In ’74 (1992)

Bootlegs have frequently captured important moments in pop history, like hearing Dylan be mercilessly heckled by the audience during the electric portion of a 1966 show in Manchester, England on the widely bootlegged (and eventually officially released) “Royal Albert Hall” recordings. Sometimes, though, they capture things artists would rather forget, or, in the case of A Toot And A Snore In ’74, had possibly actually forgotten by the morning after. The story goes that while John Lennon was producing Harry Nilsson’s unhinged opus Pussy Cats, Paul McCartney and Stevie Wonder stopped by the studio, and they all decided to jam. Since this was during Lennon’s famously debauched “lost weekend,” everyone involved is clearly wasted, and this once-in-a-lifetime meeting of the minds (and the last time McCartney and Lennon recorded together) resulted in a completely unlistenable pile of wet noodling that’s only interesting in the most morbid of ways. Standout moments on the album include Lennon offering Wonder cocaine, Lennon berating his band for not being able to follow his changes, and Wonder leading the blacked-out supergroup through a medley of Sam Cooke hits for the one shining moment of the session where everything stopped going completely wrong. [Miles Raymer]

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11. Prince, The Black Album (1988)

Like Neil Young, Prince has a habit of recording entire albums’ worth of material and then abandoning them on a whim, which has made him a boon to bootleggers, much to his very vocal dismay. In 1987, one album made it all the way to being pressed up in promo form before Prince called off its release. The copies that made it into journalists’ hands came in all-black sleeves and didn’t list Prince’s name or the title he had for the record, which may have initially been called The Funk Bible, but quickly became known as The Black Album. Its inverse-Beatles title and rapturous word-of-mouth reviews gave it a deep dose of renegade samizdat cool, but the record’s biggest attraction came from the mystery surrounding its near-release. Why would one of the biggest pop stars suddenly withdraw a finished album that everyone in the world wanted to hear? There were rumors that the music was too risqué for the label, or that Prince had freaked out on drugs and decided that the whole album was possessed by demons. It’s also possible that Prince is just a control freak who decided at the last possible minute that its more hard-funk-oriented direction wasn’t the right next move. Still, it remains a crucial part of Prince folklore, and eventually saw legitimate release in 1994. [Miles Raymer]

12. Nirvana, Roma (1994)

Until Live At Reading was released in 2009, the only official document of Nirvana’s legendarily combustive live performances at the peak of its fame was the bewilderingly spotty compilation From The Muddy Banks Of The Wishkah. Lucky for fans, Italy’s state-owned RAI Radio 1 broadcast the band’s February 22, 1994 show in Rome, and enterprising bootleggers pressed the crisp, professionally engineered recording under a number of different titles, the most popular of which was Roma (from the alt-rock-heavy ’90s label KTS). The band—in its expanded In Utero-era incarnation with Pat Smear on guitar and Lori Goldston on cello—is raggedly magnificent, and Krist Novoselic’s stage banter is phenomenally on point. In an eerie display of the speed with which bootleggers could turn around product, copies of the recording made it to market just weeks after the show, in between Kurt Cobain’s subsequent overdose in a Rome hotel in March and his suicide in April. [Miles Raymer]

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13. Danger Mouse, The Grey Album (2004)

Ironically, the bootleg record industry got hit by the internet and digital music piracy even worse than the traditional labels did. There’s no money to be made when formerly rare recordings are just a search away as free downloads and bands that had once been easy to bootleg like Phish and The Grateful Dead can sell their own live recordings directly to fans. Simple online piracy isn’t the true heir to the legacy of passionate bootleggers like Ken Douglas and Dub Taylor, though—it lacks a certain amount of flair and obsessiveness. There are still people passionate enough about music that they’re willing to find creative ways of breaking the law to express it. In fact, mashups used to also be called “bootlegs” when they first became a thing around the turn of the millennium. While it turned out to be something of a one-trick pony, the form did produce one legitimate masterwork. Danger Mouse’s brilliantly executed and, from a legal standpoint, breathtakingly daring blend of Jay Z and The Beatles blew pop music’s collective mind, and helped to prove just how much new technology and disintegrating genre distinctions had changed pop’s rules. [Miles Raymer]

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14. Jimi Hendrix and Jim Morrison, Bleeding Heart (1972)

This bootleg recording trades more on its legendary status as a meeting of the minds between two of the greatest iconoclasts of the era than for its actual musical merits. The specific date of the jam is a bit fuzzy, but it is said to have taken place sometime between March and June of 1968 at the Scene club in New York. Playing with the house band, Hendrix and Morrison run through a number of blues covers together, with the former doing his best to keep it together, while the latter typically devolves into a drunken embarrassment. Hendrix himself was apparently responsible for recording the gig, and it only became available to bootleggers after the two-track tape was stolen from the guitarist’s apartment. [Corbin Reiff]

15. The Troggs, The Troggs Tapes (1972)

The Troggs are best remembered for the seminal British Invasion hit “Wild Thing” in 1966, but they’re also renowned in many circles for this illicit recording made four years later. Not so much celebrated for musical content, the tapes became a huge hit for the sheer level of acrimony and bile spewed among the band members, with singer Reg Presley in particular teeing off on Ronnie Bond for failing to properly play a desired drum pattern. Legend has it that many producers around London and beyond would keep a copy of the tape handy and play it for nervous groups before the red light went on in the studio—to relieve some of the tension. [Corbin Reiff]

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