Green’s Dictionary of Slang

1. (US) a shrewd person.

1896		Ade Artie (1963) 84: Down at the farm, he was the wise guy and I was the soft mark.
1904		‘Number 1500’ Life In Sing Sing 264: What do you mean? I’m pinched. Well, you’re a wise guy and I’ll have to stand the guff and cave.
1904		Sydney Sportsman (Surry Hills, NSW) 8 June 6/2: If Mr. Kelly is a wise guy he woii't extend his travels.
1915		Atlanta Constitution 29 Aug. 42/3: The underworld saw John Burglar metamorphose overnight from a ‘chump copper’ to a precinct captain reputed to be a ‘wise guy.’.
1927		W. Edge Main Stem 192: Don’t try to pull that game off on me, Jack. I’m a wise guy.
1936		(con. 1920s) Dos Passos Big Money in USA (1966) 799: He carried the bankbook in an inside pocket [...] it always made him feel like a wise guy.
1941		K. Tennant Battlers 87: He was a ‘wise guy’, who knew that in his life there was enough trouble coming to you without going out to look for it.
1948		A. Wright Under the Whip 15: Not much happened [...] that the ‘wise boys’ did not get to know about.
1967–8		Baker et al. CUSS 223: Wise guy A quick or witty person.
2001		(con. 1975–6) E. Little Steel Toes 164: Abe smiles around his cigar and says, ‘Yes, they said you was a wise guy.’.

2. (US) anyone who thinks they are particularly knowing or clever; a general derog. description: the implication being that the person is too clever for their own good.

1896		F. Hutcheson Barkeep Stories 171: ‘Say, lemme tell you somet’in’, Mr. Wise Guy,’ broke in the barkeep.
1901		‘Hugh McHugh’ Down the Line 13: I’m a dub on the dope, but it was my play to be a Wise Boy [...] on this particular occasion.
1904		C. Connors Bowery Life [ebook] ‘Say, Chuck, I hear you ust to be a prize-fighter,’ said a wise guy with one of them bum wise winks.
1910		Sun. Times (Perth) 6 Mar. 2nd sect. 10/4: The ‘wise guys’ of the racing game who think that studying form closely can only result in the students beating the bookmakers, were all knocked into a cocked hat through Orline’s vic tory in the Australian Cup.
1913–14		Van Loan ‘Easy Picking’ in Taking the Count 313: You’re a wise guy, you are! [...] if this guy is a sucker, I don’t know where you get your wise ones!
1917		Van Loan ‘Levelling with Elisha’ in Old Man Curry 14: What is a sucker? [...] a foolish party who bets money for a wise boy.
1921		T. Thursday ‘Hail the Professor’ in Top-Notch 1 Sept. 🌐 Boobs are born and wise boys are unmade — thanks to the boobery.
1925		O.O. McIntyre New York Day by Day 15 Sept. [synd. col.] Some patron who desires to have his tickets ‘Annie Oakleyed,’ punched by an official puncher. This, they believe, sets them apart as ‘wise guys.’.
1930		W.R. Burnett Iron Man 15: I hope you lick that nigger because them wise boys’ll have all their dough on him now.
1936		R.L. Bellem ‘Falling Star’ in Spicy Detective Sept. 🌐 You’re damned right you haven’t got all day, wise guy. While you’ve been wasting time, I’ve had my foot on a buzzer under my desk.
1936		R. Chandler ‘Goldfish’ in Red Wind (1946) 157: We shook hands, grinned at each other like a couple of wise boys who know they’re not kidding anybody, but won’t give up trying.
c.1939		B. Bennett ‘Sobstuff Sister’ in Billy Bennett’s Third Budget 18: The wise guys and yobs payed their tanners and bobs.
1947		B. Schulberg Harder They Fall (1971) 115: As far away from the wise boys as possible.
1949		N. Algren Man with the Golden Arm 10: When I go after a wise guy I don’t care who he is.
1951		N.Y. Age 29 Dec. 14/1: ’Twasn’t so merry for the hustlers and ‘wise boys’ along the ‘Apple’ this hear.
1951		Kerouac On the Road (The Orig. Scroll) (2007) 237: Don’t worry bout that wise guy.
1952		(con. 1920s) ‘Harry Grey’ Hoods (1953) 272: A guy of the streets and off the streets. A knockaround guy. A wiseguy.
1964		H. Selby Jr Last Exit to Brooklyn 134: That wise punk Wilson tried to pull a fast one and I had to straighten im out.
1964		L. Nkosi Rhythm of Violence II iii: Was I talking to you? Why can’t you shut up until somebody talks to you! Wise-guys!
1967		F. Salas Tattoo the Wicked Cross (1981) 16: If you act up and play the wise punk, I’ll teach you something.
1968		N. Heard Howard Street 20: Gimme the bread back. And just ’cause you’s a wise guy, gimme yours too.
1977		(con. 1949) J.G. Dunne True Confessions (1979) 33: All the harp wise guys go there, tell each how long their thing is, and who they been sticking it into.
1981		G.V. Higgins Rat on Fire (1982) 133: Ya don’t have to be a wise guy, you know.
1992		R.C. Cruz Straight Outta Compton 56: ‘How much does it cost to go all the way to Brooklyn?’ LeRoy asked the driver. ‘Wiseguy, eh?’ The driver pointed to a posted sign.
1997		(con. 1970s) G. Pelecanos King Suckerman (1998) 148: Works with a bunch of wise guys.
2000		Guardian Rev. 21 Apr. 14: Wise guys hang out of cars that shudder under the pressure of hip-hop basslines.

3. (US) a criminal.

1909		H. Green Mr. Jackson 59: ‘Cheer up, my boy, they ain’t no more prisons fur you’ [...] I had to start out an’ be a wise guy again after livin’ with no effort fur mighty near a year.
1930		‘Armitage Traill’ Scarface Ch. iii: There’s been talk about you an’ her goin’ around among the wise-guys in your neighborhood.
1982		J. Ellroy Clandestine 91: ‘What's his occupation?’ ‘Gambler. Punk. Wise guy. I don't think he has a job’.
1987		T. Wolfe Bonfire of the Vanities 396: But the big-time black wiseguys, the drug dealers, they don’t want a black lawyer representing them.
1991		(ref. to 1910s) J. Breslin Damon Runyon (1992) 116: The great line between ‘citizens,’ [...] and [...] ‘wise guys’ or underworld guys, who had either been convicted for something or certainly should have been.

4. (US) as a form of personal address.

1940		W.R. Burnett High Sierra in Four Novels (1984) 323: Look, wise-guy. For fifteen years I’ve been listening to sob-stories.
1953		R. Chandler Long Good-Bye 55: ‘Well, smart guy, just to show you I’m not kidding here it is.’ [Ibid.] 84: He doubled a meaty fist. ‘Darling, think of your manicure,’ I told him. He controlled his emotions. ‘Nuts to you, wise guy.’.
1971		J. Simon Sign of Fool 8: Hey wise guy, I said turn ’em on!
1991		(con. 1920s) O.D. Brooks Legs 91: ‘Okay, wise guy,’ he grinned.
2000		P. Roth Human Stain 117: You don’t do what I ask you. Why’s that, wise guy?

5. (orig. US) a member of an organized crime syndicate, usu. the US Mafia.

1955		B. Appel Tough Guy [ebook] The wise boys down the West Side said with a wink that there must be two kinds of parole. ‘One kind the coppers hound you all the time. The other kind’s the Ownie Madden kind with the coppers kissing your ass’.
1972		G.V. Higgins Friends of Eddie Coyle 57: The brothers’re [...] getting guns from somebody that’s in with the wise guys.
1985		N. Pileggi Wiseguy (2001) 11: At the age of twelve my ambition was to be a gangster. To be a wise guy.
1989		C. Hiaasen Skin Tight 22: Name of Tony Traviola. Wise guy . . . Tony the Eel.
1999		Indep. Rev. 10 Nov. 6: At a time when the Boston Irish and the Mafia ‘wiseguys’ were killing each other in all-out war.
2001		K. Sampson Outlaws (ms.) 23: Throughout the history of wiseguys and goodfellas and that, there’s always been lads knocking on the dressing room door after the show.
2006		D. Winslow Winter of Frankie Machine (2007) 63: You ask what happened to the longshoremen [...] when they tried to get a decent wage and oragnize a union and they didn’t have the wise guys backing them up.
2010		A. Steinberg Running the Books 14: He was an old Boston wiseguy, a former bank robber and mobster.
2017		D. Winslow The Force [ebook] Mobster chic, Russo’s ironic comment on the wiseguys he grew up with and never wanted to be.
2023		Rayman & Blau Riker’s 151: Some of the COs were bringing in seafood for these wiseguys from Little Italy.