Green’s Dictionary of Slang

boss adj.

[boss n.2 (1)]
(orig. US)

1. superior, important, influential.

[US]W. Otter Hist. of My Own Times (1995) 112: The boss carpenter was awake when we entered the room; he asked us WHAT’S BROKE, said he. I told him we were on a sort of a Jerry, and wished to get a bed for that night if we could.
Solomon Secondthoughts’ [J.P. Kennedy] Quodlibet (1872) 244: The fifer was no other than Charley Moggs, long known as the boss loafer of Bickerbray .
[US]Democrat & Sentinel (Ebensburg, PA) 25 Oct. 1/4: One of the most eminent men of this class that we ever knew, was a ‘boss carpenter’’.
[US]‘Artemus Ward’ Artemus Ward in London in Complete Works (1922) 425: Not one of these common poits [...] but a Boss Poit — also a philosopher.
[US]M. Thompson Hoosier Mosaics 39: Yes, sir, he’s got me! He’s about three lengths ahead o’ me, as these boss fellers says, an’ I don’t know but what I’m distanced.
[US]News & Herald (Winnsboro, SC) 21 July 1/5: The boss catcher, Bob Scott, caught and redeemed from death a bright poodle.
[US]Nat. Police Gaz. (NY) 27 Oct. 6/3: ‘He must be the boss sucker’.
[UK]Sporting Times 4 Oct. 7/1: A city is a town where the principal church is called a cathedral and the boss parson a Bishop .
[Aus]Bulletin (Sydney) 31 Jan. 11/2: [T]he vehicle was boarded by one of Cobb’s boss employés, who, to put it mildly, had evidently anticipated Christmas, and had been where the golden corn was waving.
[US]J.A. Riis How the Other Half Lives 73: With a swinging blow of his club he knocked the faucet out of the keg and the half-filled can from the boss hag’s hand.
[US]Ade Fables in Sl. (1902) 64: If he wanted [...] everybody believe he was a Nobby and Boss Minister he would have to hand out a little Guff.
[Aus]Sun. Times (Perth) 29 Oct. 1/6: The Port’s boss bounder did in a quid over the elections.
[US]N.Y. Eve. Journal 31 Jan. in Fleming Unforgettable Season (1981) 14: Pulliam’s new fighting ‘ump’ [...] was the boss banisher of the year.
[Aus]C.E.W. Bean On the Wool Track 247: A ‘boss bullock-driver’ [...] is a considerable man. Very often he is a steady one. A ‘boss bullocky’ is a man who owns his own team, and perhaps more than one.
[US]H.C. Witwer Yes Man’s Land 7: He’ll give me a letter which would get me past St. Peter, the boss gate-tender of ’em all!
[US]J. Lait Gangster Girl 4: In Chicago the rackets were run by a bunch of boss hoodlums.
[UK]J.G. Brandon Gang War 127: If he isn’t the boss-pedlar for dope [...] then I’m the biggest dud that ever took a salary from the C.I.D.
[US]Murtagh & Harris Who Live In Shadow (1960) 88: The boss pedlar [...] Dom and Alice belong to a mob in East Harlem.
[US]Metronome Apr. 32: The arrangements by Clayton are effortless and elegant — he has always been a boss arranger.
[US]P. Hamill Flesh and Blood (1978) 26: You mean he’s the boss fag [...] Pimp of all pimps, princess of the fuck boys.
[US]G.V. Higgins Patriot Game (1985) 170: The Digger was a boss con.
[US]D. Pinckney High Cotton (1993) 33: Aunt Clara’s grandfather was a ‘boss mechanic,’ a carpenter, blacksmith, and wheelwright.
[Aus]P. Temple Black Tide (2012) [ebook] You find out a bit about the animal [...] whether he wants to be the boss horse.
[US]Ebonics Primer at boss pimp Definition: a powerful pimp with a large collection of prostitutes. Example: Dolemite is boss pimp.

2. excellent, wonderful; also intensified as boss like hot sauce.

[US]‘Artemus Ward’ Artemus Ward, His Book 229: If he had bin a sensible man he’d have put the money in a boss railroad or a gas company, and left this magnificent continent to intelligent savages.
[US]F. Remington letter in Splete (1988) 12: We are to have a boss old fight here next Saturday.
[US] in N.E. Eliason Tarheel Talk (1956) 261: If a coast man wants to express the superlative degree he says ‘That is a “Boss” log or a “Boss suit”’.
[Aus]Bulletin (Sydney) 8 Jan. 8/3: The cartoon went high; and the items were so warm / That even a D. T. man might stand up and say to all the word, [sic] ‘This is a boss paper.’.
[US]Ade Forty Modern Fables 198: I, who have taken no Precautions, am Strong as an Ox and feeling Boss.
[US]H.C. Witwer Smile A Minute 140: It’s slightly different with a woman, especially one which is a boss good looker.
[US]L. Hughes Tambourines to Glory I vi: Stacked, solid – neat, all-reet – boss, baby!
[US] ‘Mexicana Rose’ in D. Wepman et al. Life (1976) 40: I go for you, Sam, I think you’re boss.
[US]M. Braly Shake Him Till He Rattles (1964) 45: He’s got boss connections in the Filmore. He can turn stuff like this.
[US]N. Heard Howard Street 36: Man, him and his chick did a boss job on that stud.
[US]T. Southern Blue Movie (1974) 9: He began his final laugh, his boss laugh, the kind that [...] turns into a monstro cough.
[US] in R.G. Reisner Graffiti 129: Tea is a groove and AMT is really boss.
[UK]M. Thelwell Harder They Come 277: Mek him know say me coming back wid two baas song.
[US]P. Munro Sl. U. 44: That concert last night was boss!
[US]College Sl. Research Project (Cal. State Poly. Uni., Pomona) [Internet] Boss (adj.) Very cool, most excellent.
[UK]K. Sampson Outlaws (ms.) 2: Considering that it’s nearly Christmas and that, it’s a boss fucking day.
[UK]J. Joso Soothing Music for Stray Cats 70: I’d been to Soho loads of times [...] and managed to have a perfectly boss time.

3. best; often as the boss, the best.

[US]Nat. Police Gaz. (NY) 8 Nov. 11/3: ‘I’m the boss body-chopper in America; can hack, hew, pickle and brine more stiffs in less time and in better manner than any living man’.
[US]‘O. Henry’ letter in Rolling Stones (1913) 264: We have the boss trick here now. Have sold about ten boxes of cigars betting on it in the store.
[US]J. Hawthorne Confessions of Convict 145: Mother Mandelbaum, the boss ‘fence’.
[US]O. Wister Lin McLean 134: Smith’s Palace — that’s the boss hotel here.
[US]G.D. Chase ‘Cape Cod Dialect’ in DN II:vi 424: boss, adj. Used to express high commendation, as ‘She’s the boss girl.’ ‘Come, do this for me, that’s the boss.’.
[Aus]Bulletin (Sydney) 4 July 15/1: The camel is the boss kicker of the universe. Hump’s hind leg will reach anywhere.
[US]H.C. Witwer No Base Like Home 22: He came near bein’ the boss ball player I’d ever seen.
[US]H.C. Witwer Fighting Blood 305: The Rags pulls the boss boner of a lifetime devoted to making boneheaded plays.
[US]H.C. Witwer Classics in Sl. 57: As he was the boss scrapper next to the lately Duncan, why he was acknowledged champion of the world.
Minneapolis Star (MN) 12 Sept. 69/4: Boss, theres no mistaking this word. It means you are far out [...] in other words, you’re a stone gas.
[UK]K. Sampson Powder 355: Too much! Bloody, bloody . . . The fucking Boss, that’s all!
[US](con. 1960s) J. Ellroy Blood’s a Rover 23: Crutch had a ’65 GTO the boss ride.

4. of criminals, very dangerous.

[Aus]Bulletin (Sydney) 19 Sept. 22/3: He never refused to go out on a hunt for boss thieves, nor to ante-up his little pile when he bucked the tiger and lost. And he was a rustler when out with the boys.

5. (US) arrogant, overbearing.

[US]W.J. Kountz Billy Baxter’s Letters 21: He was nobby and boss. He was dropping his r’s like a Southerner, and you know how much of a Southerner Johnny is – Johnstown, Pa.

6. dedicated, obsessed with.

[US]K. Kolb Getting Straight 39: In Ward A, man. That’s for the boss nuts, the real experts.
[US]E. Bunker Animal Factory 124: He’s just a boss sucker for pretty boys.

7. important, meaningful.

[UK]K. Sampson Outlaws (ms.) 25: Like one of our own was going to break out and do something boss with their life.

In compounds

boss player (n.) [player n. (3)]

(US black) a thoroughly experienced, professional, worldly wise pimp who may even transcend pimping for superior occupations; the term can be applied to any admirable figure outside the pimp milieu.

[US]Milner & Milner Black Players 34: A pimp who takes his pimping money and opens a legitimate real estate office is said to have gone on to higher game. He is then no longer a pimp but a player; perhaps even a boss (excellent, tops) player.
[US]A.K. Shulman On the Stroll 56: He [...] instilled contempt for the small-time popcorns and respect for the real boss players.