Definition: To produce and/or distribute legally prohibited products.
Usage: Today's word is used mostly as an adjective (bootleg DVDs) (DVDs piratas?) and a verb (to bootleg DVDs). It has settled into the US vernacular as a regular verb referring to the action of bootlegging, which is carried out by a bootlegger, who bootlegs.
Suggested Usage: Remember that the original meaning of today's word began in the days of rum-runners: "Izzy Russianoff got the capital to start his charity hospital bootlegging moonshine in the 30s." However, don't let that restrain you from applying it to any product illegally distributed, "Curt's avocation was bootlegging illegal fireworks up and down the east coast until a bolt of lightning caught up with his truck on a run through the Poconos."
Etymology: Today's word originated from the habit of men, when they wore high boots in centuries past, of smuggling objects across borders by hiding them in the legs of their boots. In the late 19th century, however, its meaning shrunk to the smuggling of whisky into counties and states that were 'dry.' During Prohibition, the word became even more popular as the vocation of smuggling alcoholic beverages into the United States from Canada or from, well, bootleg distilleries. However, the word did not go the way of Prohibition. Rather, its meaning has broadened again recently to refer to the distribution of any illegal product, such as copyrighted tapes, CDs, and DVDs that are widely produced and distributed illegally today.
Fonte: Dr. Language, YourDictionary.com