Ebay has breathed new life into a traditional underground industry:
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My father's family is from Kentucky, and they bootlegged back in the early days of the 20th century. Of course they did not bootleg live or rare music; my dad's relatives were purveyors of that original ol' mountain dew. We don't know for sure if any of them was the one who first carried a bottle of illegally distilled whiskey in a hollow boot in place of his peg leg, as the legends go, but now you young'uns out there know from whence this interesting and storied term hails.
I had a very small collection of Black Sabbath bootlegs before I began my Ebay addiction in early 2001. Now, however, amongst Philadelphia Sabbath fans, I am a force to contend with if you're comparing boots of live Sabbath shows, whether on video or cd. I go for the really rare stuff, with the late Ray Gillen and those interesting shows with Ian Gillan where Sabbath plays Deep Purple's old dinosaur stomp 'Smoke on the water' (truly something I wish I'd seen live myself). I have even now waded into collecting Judas Priest boots and will soon start throwing my cash away on BOC's fan-recorded shows.
Ebay has simply made it so easy for me to find excellent recordings of shows by my favorite bands, with the kind of rarities artists never seem to include on official live albums. Thus I consider live bootlegging an honorable tradition in rock'n'roll, assisting the preservation of the legacy of artists' live performances and also their odd moments, such as my three (count'em!) different editions of Ray Gillen's recording of Black Sabbath's 'Eternal Idol' album (1986, Warner Bros.), later rerecorded by Tony Martin for the official release after he left the band. Two have different 'extras', and one has actually been remastered from the rough pre-produced version commonly available.
I've been able to acquire items from people in trade, since bootleggers are a community. Everyone seems to have something you don't have; I've only met one other Sabbath fan who seemed already to have everything. One of the other great treasures of this hobby is finding shops here and there that 'specialize' in bootlegged concerts and rarities and make it yet easier to find stuff like this, without dealing with the postal aspect of services like Ebay. It's nice to be able to browse rarities by the dozens in one place, where you can learn things about your lifetime-favorite bands that you've never known, or discover covers you never knew they did.
For those of you who are not into metal, take heart: the bootlegging tradition is alive throughout the entire spectrum of rock'n'roll and probably throughout popular music. Any band or artist you like is going to have some boots available on Ebay and probably the other internet auction services as well.
One interesting technique in selling bootlegs has also evolved on Ebay: since there is some reasonable fear of legal retribution among bootleggers, there are ways of marketing bootlegs that are quite clever, one of which is auctioning off a commonly commercially available item and giving the 'bootleg' away free, expecting that the smarter collectors will realize this tactic and push the price up for the 'free' item, but removing the bootlegger from legal liability for 'selling' the bootlegged CD.
The last thing I must say is that if anything has made bootlegging of live shows and rarities easier, it's cd burners (and now, DVD-burners). We all know that commercial music and videos are commonly bootlegged, especially outside the USA, which is a bad thing, but for the preservation of a band's live performance legacy I must praise the increasing ability of technology to enable people to publish and propagate their collections and share them. All of this has also helped largely to eliminate the notorious bane of the bootleg hobby: bad sound or video quality. All the technology and fast search/purchase trends have elminated bad boots from the mix almost entirely, and smart consumers are now able to nearly guarantee that the stuff they buy is going to be good. I can say personally that I've been extremely fortunate in collecting all of my boots, and that they're more than high enough in quality and diversity that I come back to them again and again to enjoy.
In short, this is a really good time to get involved with this hobby and build yourself a very unique cd collection.