Green’s Dictionary of Slang

1. of liquor, illegally transported, smuggled or distilled.

1885		Humeston (IA) New Era 10 Dec. 8/2: The latest scheme practiced by the boot leg saloon man.
a.1889		Omaha Herald n.p.: There is as much whisky consumed in Iowa now as there was before, ‘for medical purposes only’, and on the boot-leg plan [B&L].
1902		Baxter Springs News (KS) 17 May 1/2: Under the old bootleg system [...] a man had to buy a half-pint of squirrel poison [...] A few glasses of hop tea [...] does not have the fighting qualities of bootleg whiskey.
1922		S. Lewis Babbitt (1974) 25: There were [...] rumours of bootlegged whisky.
1925		D. Hammett ‘Corkscrew’ Story Omnibus (1966) 221: I found I knew some of her friends. A couple of them were high-class swindlers, one was a bootleg magnate.
1931		W.N. Burns One-Way Ride 95: Morgan Collins, his chief of police, launched an honest drive against the bootleg ring.
1945		J. Fishman Bullets for Two 7: With heavy taxes on legal liquor, bootleg stuff is coming back.
1953		J. Thompson Savage Night (1991) 8: He’d dropped out of the bootleg racket before the war.
1954		J. Thompson Swell-Looking Babe 18: Tug had headed a statewide bootleg syndicate.
1962		Mad mag. June 45: He makes a bundle pushing bootleg rye.
1969		‘Iceberg Slim’ Mama Black Widow 58: Whiskey was legal, but he drank bootleg stuff.
1976		Cab Calloway Of Minnie the Moocher and Me 38: Whiskey, mostly old, hard bootleg rye.
1984		C. White Life and Times of Little Richard 32: Daddy used to hide the jugs of bootleg whisky.
1996		H. Roth From Bondage 280: Ira took notice of Dalton [...] who was drinking a glass of bootleg gin.
1999		Observer Mag. 4 July 32: Home-made bootleg (or ‘bathtub’) gin was of such poor quality.

2. fake, counterfeit.

1895		Chambliss Diary 324: The menu at the meal stations along through Texas and Arizona consists of white-leather steak [...] bad-smelling butter, corn dodgers, and ‘boot-leg’ coffee.
1969		H. Rap Brown Die Nigger Die! 104: Half of the Black ‘militants’ ain’t nothing but a bunch of potheads, bootleg preachers and coffeehouse intellectuals.
1997		A. Frewin London Blues 11: I paid £15 for this bootleg tape.
1997		C. Hiaasen Lucky You 74: He became known throughout the county as a reliable supplier of bootleg wheelchair emblems.
2000		Indep. 5 Feb. 19: At least six times as many copies of the album, all of them bootleg, have been sold there since [Ibid.] Bootlegged cassette tapes are sold on the street for the equivalent of 30p.

3. illegal in general.

1928		Daily Express 5 Mar. 11/6: Bootleg [i.e. smuggled] baby.
1931		W.N. Burns One-Way Ride 37: Torrio and Capone invaded Cicero in October, 1923, and annexed it like a conquered province to their bootleg kingdom.
1942		N. Algren Never Come Morning (1988) 137: A world of alleys, side streets [...] padlocked poolrooms and bootleg bookies.
1956		‘Ed Lacy’ Men from the Boys (1967) 57: The bootleg boxing bouts when a carload of us ‘amateurs’ would tour in a battered heap [...] fighting each night under a phony name.
1973		L. Ambers in Heller In This Corner (1974) 179: I started [boxing] in 1929, in bootleg shows.
1986		J. Ellroy Suicide Hill 140: ‘[A] bootleg message service.’ ‘What's that?’ ‘A two-way answering service. Mostly it's used by parole absconders and their families’.
1995		(con. 1985–90) P. Bourjois In Search of Respect 109: The Social Club was raided half a dozen times, because it doubled as a pool hall and bootleg bar.
2000		Ebonics Primer at www.dolemite.com 🌐 bootleg Definition: stolen. Example: None of my shit is bootleg. So, step back.

4. (US teen) in fig. use, second-rate.

1997		Eble Campus Sl. Apr. 2: bootleg – cheap, imitation, copied: ‘Her hairdo is bootleg’.
2002		Teen Lingo: The Source for Youth Ministry 🌐 bootleg adj. Newer term to replace ‘ghetto’. Something that is an imitation, cheap or of bad quality. ‘oooh, that Macaroni and cheese was bootleg!’.