As a noun, bootleg means the top part of a boot, the part that is around the leg instead of the foot. From the practice of hiding small items in a boot to smuggle them past the authorities, the word became a verb, meaning "to smuggle", and an adjective, describing something that has been smuggled (or, more rarely, stolen). Anything that is regulated can be bootlegged, so the term now often refers to such items as audio or video recordings not released by whoever holds the rights to them (also known as "pirated" copies), to cigarettes on which the required taxes have not been paid (also known as "black market" cigarettes), and to jeans or other clothing with phony (or "counterfeit") manufacturers' labels on them. It is also the name given to a type of American football play.
Alcohol smuggling
The traditional meaning of "bootlegging", going back to Prohibition in the U.S., is selling liquor on which the federal taxes have not been paid. The term is sometimes mistakenly used to refer to making untaxed alcoholic products, but, properly speaking, that is "moonshining", not bootlegging (although a bootlegger may be working with a moonshiner, selling or delivering the liquor for that manufacturer). Most bootleg liquor is not "home-made" by a moonshiner but, instead, bottled by professional distillers: During Prohibition, much of the bootleg whiskey in the U.S. was brought in from Canada and much of the bootleg rum from Mexico or Cuba, but today most bootleg alcohol in the U.S. is made domestically but sold "under the table" or "off the back of a truck" without the necessary permits and taxes. Smuggling of cigarettes instead of alcohol (i.e. from low-tax to high-tax states) is sometimes called "buttlegging".
Unlicensed music
A bootleg recording is one that was not officially released by the artist (or their associated management or production companies). Sometimes they consist of works-in-progress or discarded material distributed against the artist's will; these might be made from master recordings stolen from a studio or label, or from demo recordings not meant to be shared with a wide audience. Bootleg albums can also be recorded "unofficially" with gear smuggled into a live concert -- virtually all artists and live venues prohibit such recording, but modern portable technology has made it increasingly easy to do.
Many bootleg albums have since been released officially by the copyright holder; for instance in 2002 Dave Matthews Band released Busted Stuff in response to the success of the "Lillywhite Sessions" album which they had not intended to release; The Beatles' release of their Anthology albums effectively killed the demand for many Beatles bootlegs previously available; and Bob Dylan has released an entire bootleg series, which as of 2003 had five volumes.
A few artists like Peter Gabriel and Duran Duran have responded to the demand for bootleg concert recordings by experimenting with selling "official" bootlegs made directly from the live soundboard feed, and thus superior to surreptitious audience recordings which are typically marred by crowd noise and muffled sound; these are generally available a few days to a few weeks after the concert. A newer business model allowed by improving technology in high-speed CD reproduction can make these "official boots" available to audience members as they leave the concert; however, a key patent in the process has been bought by media giant Clear Channel Communications, which appears to be stifling competition and development of the process.
Recently bootlegs have become the term for melding two music records into each other to make a new piece of music out of two old components. Among the most popular artists in this genre are The Freelance Hellraiser, Soundhog, Go Home Productions and Lionel Vinyl. These type of records area also referred to as mash ups or bastard pop.
Bootlegging can also refer to the unlicenced filesharing of copyrighted music.
American football play
In American football, a bootleg is a play where the quarterback runs with the ball in the direction of either sideline behind the line of scrimmage. This can be accompanied by a play action, or false hand off to a running back running the opposite direction.
The quarterback can be accompanied by an offensive lineman to block for him, or run without a blocker, which is known as a naked bootleg. If more than one offensive lineman moves with the quarterback to block, the play is known as a rollout. After escaping the area behind the offensive line, the quarterback may either throw a pass downfield or run with the ball himself to gain yards.
The play is called to confuse the defense, by moving the quarterback away from where they expect him to be, directly behind the center. The quarterback's motion also may attract the attention of the defensive backs, allowing one of the receivers to become uncovered. The play is typically used by teams with mobile, or fast, quarterbacks, such as Michael Vick, Steve Young, and Randall Cunningham.