As one of the last demographic members of Generation X, spanning the cultural gap between cassette tapes, Napster, and hipsters, the word bootleg has found its way comfortably into my vernacular. A word that once literally meant the top portion of a tall boot, or the leather that made up the top of a boot, it has become an iconic term for an ironically nostalgic culture of on-demand content, freedom of information, and memetic de-evolution. The bootleg culture is accelerated, saturated, and exposed.
The most sure-fire way to create an underground market is through taxation and prohibition. As early as the 16th century, the taxation of alcohol resulted in the illegal smuggling of rum between colonies. Rum runners were usually pirates or merchant sailors who would transport the contraband along with their trade cargo. It is speculated that during the American Civil War, soldiers would conceal flasks of liquor in their boots, or under the leg of their trousers, hence the term bootleg, deriving the name of the action by its method of execution. During the prohibition of alcohol in the 1920's, bootlegging flourished in the United States. Legends of Appalachian rum runners, moonshiners, and mob bosses continue to fascinate us.
Google "bootleg" and you're sure to find more results on music than liquor. A more contemporary folktale, the music bootlegger has increasingly become a problem for musicians, record companies, and shareholders since the 1960's, when unlicensed or unofficial recordings began to find their way from the preproduction studios to eager consumers without copyright. In strict definition, a bootleg is different from pirated material such as a burned cd or peer-to-peer download. Bootlegs are illicitly or unauthorized distribution of material that is not commercially released, while pirated or counterfeit material is simply an unauthorized duplicate of post-production material that has been published. Bootlegs often recordings of live performances, alternate or deleted recordings, demos, and promotional content.
The advent of the internet completely revolutionized the music industry, throwing concepts of copyright and intellectual property, and traditional methods of distribution and marketing, completely out the window of Rick Rubin's office at Sony headquarters. Peer to peer file sharing reduced much of the music industry to tears of outrage, and spawned legal action against peer-to-peer intermediaries, such as Napster, eMule, SoulSeek, BitTorrent, and ISOhunt, not to mention the infamous lawsuits filed against Napster by Metallica and Dr. Dre.
The effects of internet file-sharing have helped to produce a culture of accelerated, on-demand media consumption. Outside of the economic effects of this change, the music industry was shaped by the redefinition of content. With the entertainment world at their fingertips, it was not enough to have access to the newest singles and releases, or a massive catalogue of our favourite artists. When we discovered a way to access free distribution of unlimited content, we began searching for bootlegs. We grew up with our parents telling us that we were unique and special, and our music had to reflect that. So we sought obscurity and rarity instead of popularity and top 40. Instead of pretending to know who a We were on our way to making a successful industry based on quality, meaningful content, but somewhere along the way the demand outweighed the supply and we broke open the floodgates. Now, in order for the music industry to survive, major labels have to sell concert tickets, promotional material, advertising space, and ringtones instead of music. They can no longer risk an uncertain investment so any original content has to be produced on an independent level, artists swimming upstream against a strong current of user-generated content. The music industry has become memetic, absent of translation and interpretation, capable only of being copied. We wanted the bootleg, we asked for the gritty underground, and I guess we got it, but we lost something meaningful along the way.
 Inside joke: Infamously, Rick Rubin, the legendary record producer and co-president of Columbia Records, refuses to work from an office, and has never held one. See Lynn Hirschberg, "The Music Man." The New York Times, September 2, 2007. http://www.nytimes.com/2007/09/02/magazine/02rubin.t.html?pagewanted=all