Bootlegging refers to the practice of illegally selling, transporting or producing liquor.

In the early 1900s, in the United States heavy taxation was implemented in an attempt to regulate the liquor industry. Between 1920 and 1933 prohibition was instated and the act of bootlegging turned into a well organized crime, involving gangsters such as Al Capone and Legs Diamond. Liquor was shipped to known customers and to Speakeasys, avoiding any taxation or confiscation.

It is said that the term bootleg comes from federal troops that hid liquor in their bootlegs, during the Civil War.

1. "Bootlegging," The Columbia Electronic Encyclopedia, Sixth Edition.
2. "Bootlegging," Encarta® Online Encyclopedia 2001
More generally, to bootleg is to transport contraband of any sort. While the term originated during Alcohol Prohibition in reference to the carrying of contraband alcohol in one's boot, it has survived long enough that distributors of FDA-unapproved AIDS medicines have been described as bootleggers. (So, for that matter, has Han Solo.)

Bootlegging is also the second-most-common term for the act of distributing proprietary software in violation of copyright law. The most common term is, of course, piracy -- a term whose usage has the unfortunate connotation that one believes copyright violation to be morally equivalent to rapine, robbery and murder on the high seas.

The image of the bootlegger, like that of the seagoing pirate, is a somewhat romantic image and may seem ill-applied to unwashed warez d00dz. Nevertheless, copyright violation is a crime of contraband, not a violent crime like piracy at sea.

Bootlegging is also the term used for the creation and sale of copies of illegal recordings - specifically live recordings, outtakes and other material the creator hasn't authorised for release. These recordings, reasonably enough, are called bootlegs.
Bootlegging is distinct from piracy, which is the creation of unauthorised copies of released recordings. Many people find bootlegging more morally acceptable than piracy because bootlegs tend only to be bought by people who already own all the legitimately released recordings of the artist, while pirate copies take revenue away from the copyright holder.
Some famous bootlegs include:
Smile - the Beach Boys
Great White Wonder - Bob Dylan
Get Back - The Beatles
But almost every artist with a substantial following, from Eminem to the Beautiful South will have a plethora of poorly recorded live CDs available at your local record fair...

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