bad boy, n. — Green’s Dictionary of Slang

bad boy n.

[bad adj. + SE boy]

1. a tearaway, a young criminal.

1929		E. Booth Stealing Through Life 250: ‘Where’s Peck’s bad boy?’ the sheriff called into the cells.
1930		M. Fiaschetti You Gotta Be Rough 62: As a property owner [...] the criminal element didn’t make any hit with him [...] , and the more bad boys that went to jail, the better.
1971		E. Wilson Show Business Nobody Knows 141: One of the bad boys, a mobster named ‘Pretty’Amberg, had a fondness for puncturing people’s faces with a fork.
1988		D. Woodrell Muscle for the Wing 28: He wore a black coat with narrow lapels, a white shirt and a string tie, all in accordance with the resurging style of the rockabilly bad boy.
1996		Weekender (Wilkes-Barre, PA) 8 Feb. 41/1: There can be a difference between [...] macho assholes [...] and ‘bad boy’ types with charm.
2000		W. Shaw Westsiders 269: The trouble is, Sneak has been a bad boy for too long.
2012		T. Piccirilli Last Kind Words 227: If she went for bad boys she could still go for smarter.
2021		T. Pluck Boy from County Hell 77: Shooter, the bad boy turned lawman’s friend.
2023		Rayman & Blau Riker’s 255: Fuck all that bad-boy shit.

2. (US black) a general term of approval, referring both to individuals and to objects.

1953

L. Durst Jives of Dr. Hepcat (1989) 9: When I pin you daddio the wagon in here, and you lodes my heart on. You don’t pack no six gun, but you are a bad bad boy, and for you my lid always flip.

3. (UK black, also bad bwai, bad bwoy) in positive use, a black youth who rejects the second-class role offered by the dominant white society.

1956		C. MacInnes ‘A Short Guide for Jumbles’ in England, Half Eng. (1960) 26: A peculiarity about any coloured ‘bad boys’ one may encounter is that [...] they often seem delightful personalities.
1999		(con. 1979–80) A. Wheatle Brixton Rock (2004) 3: Feeling he must keep up his ‘bad bwai’ pose [etc.].
1999		Guardian Rev. 3 July 9: The burgeoning attraction between her and Orin, a young ‘bad bwoy’.
1999		Indep. Rev. 25 June 12: Some astonishing Jamaican gangster sequences featuring a hilarious Kingston bad-boy called Lennox.
2014		Stormzy ‘Shut Up’ 🎵 If you got a G-A-T bring it out / Most of the real badboys in the south.
2020		G. Krauze What They Was 63: [M]e see how unu badboy fi true.

4. (US) anything considered impressive.

1981		W.D. Myers Hoops 85: I poured myself some of the rum, drowned that bad boy in some Coke .
1983		R. Price Breaks 156: Tell them to get it the hell out of room 220 so I can move in the way I was supposed to, and this bad boy’s yours.
1991		D. Simon Homicide (1993) 323: I saw an ad for one of these bad boys [i.e. a gun].
1992		R. Price Clockers 224: If I did [have a gun] I’d sell it [...] I’d sell the shit out of that bad boy.
2002		D.H. Sterry Chicken (2003) 82: Ya better git that badboy [i.e. a large penis] out, or there’s gonna be trouble here ta-night!
2003		Simon & Alvarez ‘Backwash’ Wire ser. 2 ep. 7 [TV script] You get this bad boy [i.e. a concealed microphone] within ten feet of any conversation, asounds like Chuck thomspon doing play by play.
2006		C. Hiaasen Nature Girl 235: I could inhale a whole box of those bad boys [i.e. doughnuts].
2012		Cape Argus (SA) 31 Jan. 🌐 Grand Cherokee a bad boy among SUVs.
2022		J. Hannaham Didn’t Nobody Give a Shit 108: [of shoes] Ise like, There ain’t no motherfucking way I could afford two a these bad boys.

5. used self-referentially, oneself.

1996

T. Wolff ‘The Chain’ in The Night in Question 143: ‘Prime rib for this bad boy. Rare. Taste of blood, eh, Brian?’.

6. (N.Z. prison) a firearm.

2001

D. Looser Boobslang [U. Canterbury D.Phil. thesis] 11/2: bad boy n. a firearm.