Green’s Dictionary of Slang

1. (US) a general term of address, sometimes sincere, often ironic.

1918		A.P. Mckishnie Willow, the Wisp 279: ‘Hold on, ‘Big Boy,’ he called .
1923		Alberta Hunter ‘Someone Else Will Take Your Place’ 🎵 Hit that thing, big boy!
1929		D. Parker ‘Big Blonde’ in Penguin Dorothy Parker (1982) 207: Snap it up there, big boy.
1939		P. Hamilton To The Public Danger 78: Okey-doke, big boy!
1941		Batman No. 4 8: Come ahead, big boy!
1951		S.J. Perelman letter 23 Nov. in Crowther Don’t Tread on Me (1987) 119: The phrase ‘Fuck you, big boy’ trembled on my lips.
1960		D. Lytton Goddam White Man 136: I say O.K. big boy, I win.
1970		San Diego Sailor 18: You sure can dish it out, big boy.
1981		A. Weller Day of the Dog 128: Well, big boy, don’t get lost in your coat.
1984		W. Murray Tip on a Dead Crab 162: [to a horse] Hey, big boy.
2001		Guardian G2 20 Mar. 18: Fancy yourself, do you, big boy?

2. (US black) a foolish, reckless, devil-may-care young man.

1922		Eve. Public Ledger (Phila., PA) 6 Sept. 2/1: Federal agents yesterday arrested two Negroes believed to be active in drug tgraffic. teh men are ‘slated’ as melvin Mullin [...] alias —‘Big Boy’ [etc].
1928		R. Fisher Walls Of Jericho 145: ‘Got the big boy goin’, huh?’ grinned Pat.
1942		Z.N. Hurston ‘Story in Harlem Sl.’ in Novels and Stories (1995) 1008: Big boy: stout fellow, in South it means fool.

3. (US) a superior person or one who claims to be so; also attrib.

1929		M. Bodenheim Sixty Seconds 33: She respected his huffy, sassy, big-boy attitude.
1930		M. Fiaschetti You Gotta Be Rough 46: What I wanted to do was give him a chance to choose between taking a stretch or tipping me off as to the big boys of his smart set.
1940		F.S. Fitzgerald ‘No Harm Trying’ in Pat Hobby Stories (1967) 123: The Big Boys would have some way of killing it.
1948		(con. 1944) N. Mailer Naked and Dead 227: It’s the big boys, they’re scared of us.
1952		Lait & Mortimer USA Confidential 207: She discreetly supplies girls for big boys like bankers, industrialists and rich gangsters.
1967		(con. 1920s) J. Thompson South of Heaven (1994) 95: The big boy didn’t tell you, huh?
1977		E. Bunker Animal Factory 5: The big boys down town are watching this one.
1988		H. Gould Double Bang 110: The old man would tell him stories about how everything was fixed so the ‘big boys’ could make money.
1993		M.B. ‘Chopper’ Read How to Shoot Friends 35: In the company of the big boys he was just a hanger on.
2007		A.C. Shepard Woodward and Bernstein 19: He made it clear he was one of the ‘big boys’ and not to be confused with the humble copyboys who ran errands.

4. (US Und., also B.B., big fella) the head of an organized crime syndicate, or some equivalent figure.

1928		Phila. Eve. Bulletin 5 Oct. 40/3: Here are a few more terms and definitions from the ‘Racket’ vocabulary: [...] ‘the big boys,’ men in power.
1929		W.R. Burnett Little Caesar (1932) 12: The Big Boy can’t fix murder.
1930		J. Lait Gangster Girl 7: The Big Boy, as they called him (and it was abbreviated to B. B.) rarely came there.
1939		R. Chandler Big Sleep 164: I think the big boys have told Puss Walgreen to move on.
1949		W.R. Burnett Asphalt Jungle in Four Novels (1984) 143: He was A number 1 with all the big boys.
1956		‘Toney Betts’ Across the Board 213: The glib, flashy prankster says to The Champ: ‘How much insurance do you carry?’ ‘Why?’ ‘The Big Fella is lookin’ for you.’.
1958		R. Prather Scrambled Yeggs 128: ‘Who’s the boss?’ I yelled. ‘Give it to me straight or you’re dead. Who’s the big boy?’.
1960		C. Cooper Jr Scene (1996) 79: Maybe the Big Boy won’t let The Man ease out.
1970		‘Red’ Rudensky Gonif 94: Too many of the big boys are afraid that Red’s too hot too handle.
1975		I. Cameron Crime Films 88: A phrase we have heard earlier from the lips of The Big Boy, the city’s ultimate crime boss.
1987		(con. 1970s) J. Pistone Donnie Brasco (2006) 330: Don’t play around with the big boys.
2000		G.V. Higgins At End of Day (2001) 93: He’ll think he’s one of the big boys, if he’s nailed the whole world’s ended.
2011		‘Jack Tunney’ Split Decision [ebook] If you want the big boys to notice you, you don’t leave loose ends to run out of town.

5. (US) a 100-dollar bill.

1943

I. Wolfert Tucker’ s People (1944) 58: I can’t use a big boy like this, boss. Scare the bar tender to death if I flash this one on him.

6. (US) a shotgun.

1970

in DARE.

7. (W.I., also big-bwoy) an affectionate term for a foolish person.

1995

Francis-Jackson Official Dancehall Dict. 5: Big-bwoy the lovable idiot of Jamaican folklore; village idiot.

8. attrib. use of sense 7.

1930

M. West Babe Gordon (1934) 97: A happy, big-boy expression lighted the Bearcat’s face.

9. (also big boy upstairs) see big boss, the n.