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bootleg (n.)
also boot-leg, "upper part of the leg of a boot," 1630s, from boot (n.1) + leg (n.). As an adjective in reference to illegal liquor, 1889, American English slang, from the trick of concealing a flask of liquor down the leg of a high boot. Before that the bootleg was the place to secret knives and pistols. Extended to unauthorized music recordings, etc., by 1957.
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bootlegging (n.)
also boot-legging, 1890, from bootleg (q.v.).
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bootlegger (n.)
also boot-legger, 1889, from bootleg (q.v.). The word enjoyed great popularity in the U.S. during Prohibition (1920-1933), and the abstracted element -legger was briefly active in word-formation, e.g. meatlegger during World War II rationing, booklegger for those who imported banned titles such as "Ulysses."
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