etymology

"Wiseguy" can mean a made man in the mafia or a smart ass who acts like they are smarter than others. What I find interesting is that the Cantonese/Chinese slang term 古惑仔 (Gu Wac Zai) has basically the same dual meaning. In this case, it's someone in the Chinese triad, or a mischievous/cunning person.

Pure coincidence? Or does anyone know if there's a connection between the two slang words?

Best Answer

Harold Wentworth & Stuart Flexner, Dictionary of American Slang (1960) includes this entry for "wise guy":

wise guy 1 A person, usu. a male, who is aware of contemporary happenings; one who is hep; one who is hep; most freq.used ironically. Since 1910. --> 2 A person who thinks he knows everything, a smart aleck; one who says everything he thinks, one who gives advice and criticism freely; a troublemaker. Since 1910, common since c1925. 3 An egoistic extrovert, often with a cynical and superficial philosophy of life, who delights in offering sarcastic suggestions and making jokes at the expense of the pride of others.

Early print instances of 'wise guy'

Searches of the Google Books, Hathitrust, and Chronicling America databases indicate that "wise guy" used as in definitions 1 and 2 of the Wadsworth & Flexner entry go back to the early 1890s. Although it is difficult to prove a negative (in this case, that there is no connection between "wise guy" and "gu wac zai" in an East-to-West direction), it may be helpful to review published instances of "wise guy" from the earliest period (1891 to 1896) to see whether they invite any broader conclusions about its demographic origin.

From "A Policeman's Advice" in the Cleveland [Ohio] Gazette (April 18, 1891):

Saw a case of it the other night. Two young fellows had some words; the trouble was patched up by a mutual friend, and they went on arm in arm. But I knew what was coming., and I leaned up against a lamp-post and watched them. Two minutes later I had to run a block to pull them out of the gutter where they were rolling around while the mutual friend kept calling to them to stop. Why didn't he step in? He was too wise a guy. Many a man has got his head pounded for acting as peacemaker.

From "Coming of the Big Un," in the Omaha [Nebraska] Daily Bee (February 15, 1892):

It is not thought probable that a match with [Paddy] Slavin will be made, for the [John L.] Sullivan party think that [Peter] Jackson will fix Francis Patrick in such shape that his stellar aspirations will be quenched, and even should Slavin win Charley Mitchell is too "wise a guy" to allow the Australian to get hurt, as he surely would be if he met the Boston boy.

From "The Spirit That Wins," in the St. Paul [Minnesota] Daily Globe (October 2, 1892):

In significant contrast to all this powerful uncertainty in the Democratic ranks is the action of the Republican wire-pulling managers. Although two conventions have been called by the Republican county committee, great care has been taken to have a sufficient interval between for the inside manipulators to get in their fine work. In many wards practically the same delegates are slated to be in both conventions. And right here the "Kids" are "working their graft." Dar Reese is now a resident of the Second ward, not entirely without design. He is expected to fix it right so far as the county delegations are concerned. George Lamb, of course, still worries along in the Third, and his work is already assigned. In the Fourth, Henry Johns will be the "wise guy" of the younger protective pluggers. The Fifth and Sixth ward workers have been picked and fixed for possible combinations, and in the Seventh Judge Schoonmaker is to manage the maneuvers to accomplish what is aimed at.

From "Testimony in Slang: Language of a Chicago Policeman That Would Perplex the Average Jury," in the Wheeling [West Virginia] Sunday Register (April 29, 1894), evidently taken (without credit) from a Chicago, Illinois, newspaper item:

"Tell the jury how it was that you met them [the three defendants]."

"Oh, yes. Well, it wuz jist dis way: Me an' me pardner wuz doin' a walk on State street. We sees de tree blokes. Dey wuz doin’ a hold-up. De wise guy on de end of de bench dere, he hed a gun an de oder two cadgers, dey wuz doin' de garotte on the victim. I pulls me smoke wagon—me gun, ye know—an' me an' me pardner, we makes a sprint for 'em. I blazes twice. De wise guy drops. I makes de pinch an' turns him in."

"Pardon me," shouted the defendant's attorney, "but we have a constitutional right to have this case tried in the English language. What do you mean, officer, by the 'wise guy' and 'sprints.' and 'cadger,' and such like expressions?"

From "A Six-Story Brick Plant," in the [Indianapolis, Indiana] Clay-Worker (June 1894):

For a long time I had quieted the whisperings of conscience by assuring mys4elf that it was well to have one man on a paper who didn't know the whole thing. I felt that my ignorance was so dense that it bordered on the grand, the heroic, the sublime. Like ignorance on a monument smiling at the wise guy, I might even say.

From "Roxey Dined a Push," in the St. Paul [Minnesota] Daily Globe (December 25, 1894):

"I know 'em all," said the other hasher, and Dutch told him to close his face, as it didn't happen to be his turn to speak.

"I'm the main pipe of the occasion," said Dutch, "and you wise guys who think you know it ail has saw your day. See?"

From "Sporting World," in the Anaconda [Montana] Standard (January 5, 1895):

Aside from his peculiarly handy manner of putting men out by conversational and other means, Jim Corbett has faculties which have won for him the prestige of a "wise guy," among these who are devoted to the manly art, either as patrons or professors.

From "In Hotel Corridors" in the St. Paul [Minnesota] Daily Globe (January 15, 1895):

J. D. Allen, the ambitious Mower county man who is contesting John Furlong's seat in the house, looks like a younger man than he is. His plan of campaign develops his age, at least in that sort of knowledge that would entitle him to be known as "a wise guy." Having made up his mind to camp on Furlong's trail, Br'er Allen proceeded to engage all the trained scouts of the Austin bar.

From a headline in the St. Paul [Minnesota] Daily Globe (June 2, 1895):

Comiskey Smiled: At the Prediction of the Would-Be Wise Guy of the Beer City: St. Paul's Club Will Stay: Saints Will Be Strengthened to Prize Form in Short Order

From "Diamond Dust" in the St. Paul [Minnesota] Daily Globe (June 17, 1895):

Capt. Comiskey finds on every corner a "wise guy" who is willing and anxious to tell him how to run his ball club, and where to place his men. Charlie was in the business before those wise fellows went crazy.

From "Language Itself: Thieves' Parlance and the Extent to Which It Prevails," in the [Mineral Point, Wisconsin] Iowa County Democrat (July 4, 1895), reprinted from the Cincinnati [Ohio] Enquirer:

When you "get to a guy," you mean that you have succeeded in approaching him. "A wise fellow" is one who knows a thing or two, but a "dead wise guy" is one who is up lo everything and could not be swindled at any game.And on the other hand a "dummy" is one who is not well versed in the ways of the world.

From "Two Great Championship Races," in the Omaha [Nebraska] Daily Bee (July 21, 1989):

Hugh Nicol has been in Chicago and Cincinnati looking up talent for 1896. There's no danger of Little Nick's getting left another year. He's a wise guy.

From "Dog Days," in the Indianapolis [Indiana] Journal (August 21, 1895), reprinted from the Chicago [Illinois] Record:

I can slobber all winter / And no one will / Offer objection. / But let me slobber / In August / And I have to begin / Ducking bullets. / Also I have to walk / Very slowly. / If I trot / Some wise guy yells. / And tells everyone to / Look out!

From "Sports for Hazy Autumn," in the Omaha [Nebraska] Daily Bee (September 8, 1895):

C. W. Williams, the individual who is forcing the big, long-winded trotting session along at Galesburg, was one of the knowledgous trotting horsemen who would lend no aid toward defeating the anti-pool selling bill passed by the last Illinois legislature. He was one of the wise guys who knew that the pool box was not concomitant to the success of the trotting turf and he promised to show a doubting world what he knew this campaign. Yet he has failed to keep his word, but, instead, has demonstrated how utterly impractical is a trotting meeting without the allurements of this magic box.

From "Bicycling," in [New York City] Truth (October 26, 1895):

For nearly an hour, while this same girl and instructor careered around the rink, men had been waiting. He wanted a lesson. "Git on!" said the instructor, pushing a wheel toward him. "Ever rode before?"

The man made a crude effort to get into the saddle. The instructor was holding the wheel with one hand and talking over his shoulder with the girl. The bicycle fell and so did the man. "This is a wise guy I've got, ain't it?" said the instructor to the girl, as he stooped to pick up the wheel. "You just keep your eye on him."

From "The Colonel Tells of His Travels with a Circus," in the Wheeling [West Virginia] Register (November 24, 1895), reprinted from the St Louis [Missouri] Republic:

'I'm glad you're on' says Mac. 'Now, some people might call it stealing, but they ain't in the circus business. We don't call it stealing, because we know it ain't stealing. We know that by getting hold of as much as we can of other people's money as the world goes round we save them a great deal of trouble and sorrow, because if we didn't take part of it some wise guy is liable to jump in some time and steal it all.

From "Notes" in the [East Aurora, New York] Philistine: A Periodical of Protest (February 1896):

The impressionistic picture conjured up in the excited mind of the pale but defiant entertainer was that Chicago, startled out of its rawhide boots at this threat of brain-waves rampant, would stampede the sacred apartments of the undefiled and snatch the prairie literati bald-headed. There had arrived a moment when the blushing, the palpitating host could not tip his laurel at a wise guy angle over his eye and say "shoo" real loud at rabid possibilities in a supositious mob. The squall for assistance was prettily timed and cautiously secret, but chiefs of police are difficult upon occasion.

From George Ade, Artie: A Story of the Streets and Town (1896):

"Of course life in the city is much different," said Miller.

"Well I guess yes. I know this town like a book. I can begin at the first card and go through the deck, but out there—they lose me. They had me lookin' like a Reub all the time.The worst one was the hired hand. His name was Elias. I see him up here the time of the World's Fair, dodgin' cable cars and lookin' up at the skyscrapers. He was dead lucky to get out o' town without havin' his clothes lifted, and, at that, I ain't sure he did. But down at the farm, he was the wise guy and I was the soft mark. ...

...

"What kind of wheel are you going to get?"

"Now you've got me guessin'. I've talked to twenty wise guys that've been ridin', and every one of 'em sings a different song. Every guy cracks up his own wheel, and says all the others is made out o' sheet iron and bum castin's.

Assessment

The earliest matches cited above tend to use "wise guy" unironically. But very soon use of the expression seems to fall into one of three categories of usage: an experienced, knowledgeable, or astute person (used admiringly); a would-be knowledgeable or hep person (used sarcastically); or a know-it-all (used disapprovingly). The first group can be subdivided further into people admired for their insight and sagacity and people who are admired for their expertise at various dishonest or even criminal arts.

One interesting point made in the Wisconsin newspaper article from July 4, 1895, is that the word guy for man shows up multiple times in thieves' slang: a "good guy" (a man with money; a "strong-arm guy" (a violent highwayman or footpad), a "right guy" (a man who can be trusted), and a "wrong guy" (a man under suspicion). Guy thus seems to have functioned in U.S. thieves' slang very much as cove did a hundred years earlier in London thieves' slang.

The occupations or pastimes in which early instances of "wise guy" most frequently arise include sports (boxing, horse racing, cycling, and baseball), crime, and politics. Admittedly, those are also the topics that newspapers devote the bulk of their attention to.

In terms of geography, the greater U.S. Midwest—Minnesota, Nebraska, Illinois, Indiana, Wisconsin, Ohio, and Missouri—is heavily represented in the early results, with especially numerous instances from St. Paul, Minnesota, and Omaha, Nebraska. By 1896, the slang usage seems to have been well on its way to nationwide recognition and use. Nevertheless, its occurrence in one of George Ade's novels in 1896 may have given it the additional cachet it needed to win over outlying areas of the country.

In all of this background, I see no indication that the Cantonese slang expression that the poster asks about played any role in the origin or popularization of "wise guy." It is tempting to see the wording "too wise a guy"—which appears in both the earliest (April 1891) and next-earliest (February 1892) instances cited above—as the forebear of the compact term "wise guy." But there is far too little data to offer firm support for that conclusion.