Green’s Dictionary of Slang

1. (also old cove) an old or older man; esp. as the old boy, one’s father; often as a term of familiar address.

1600		Shakespeare Twelfth Night III ii: Did she see thee the while, old boy? tell me that.
1608		Dekker Honest Whore Pt 2 (1630) IV ii: cand.: I drinke [...] To the old Countesse there. hors.: To me, Old Boy?
1668		Etherege She Would if She Cou’d III ii: How now old Boy!
1697		M. Pix Innocent Mistress IV v: I warrant ye, and shan’t we have such lusty treats, old boy?
1706		R. Estcourt Fair Example V ii: My Wife is an Angel, this Gentleman, a Man of Honour – and I am no Cuckold, old Boy – that’s all.
1715		S. Centlivre Gotham Election I i: Come, for once, serve yourself and your Country, old Boy.
1741		Richardson Pamela (1813) 408/1: Never fear, old boy, said Sir Charles, we’ll bear our Parts in Conversation.
1762		Bridges Homer Travestie (1764) I 85: Bravo! old boy! the king replies.
1786		F. Pilon He Would be a Soldier V ii: Here is the money, my old boy.
1796		Sporting Mag. Nov. IX 82/1: How you stare! you don’t know nothing of life old boy.
1797		‘T.B. Junr.’ Pettyfogger Dramatized II vi: He was a fine old boy.
1809		B.H. Malkin (trans.) Adventures of Gil Blas (1822) I 129: The lady of all work crammed a napkin under the old boy’s chin.
1819		R. Waln Hermit in America on Visit to Phila. 64: The ‘old boy’ would’nt [sic] let them have the music.
1825		Pierce Egan’s Life in London 20 Feb. 35/3: ‘Come, old boy, let’s shake hands’.
1827		T. Morton School For Grown Children I ii: Then there’ll be more when the old boy retires, you know.
1832		Egan Bk of Sports 84: No, no, my Old Boy [...] I will not trouble you to write an epitaph on my account.
1841		D. Boucicault London Assurance in London Assurance and other Victorian Comedies Act III: Keep the old boy away.
1849		Sam Sly 21 Apr. 4/1: I say, old boy, is Doctor Thompson’s bill paid yet?
1850		A.C. Mowatt Fashion II i: How the old boy frets and fumes over those papers, to be sure!
1854		Thackeray Newcomes I 287: God bless you, old boy; don’t be too hard upon me.
1863		T. Taylor Ticket-Of-Leave Man Act IV: Now, fork out the pictures, old boy.
1873		J. O’Connor Wanderings of a Vagabond 148: Well, thar’s Cotton; give ’em a hug, ole boy!
1880		G.R. Sims Three Brass Balls 36: Dear Ole boy.
1884		Sporting Times 20 Dec. 5/4: Masher E.: ‘What Babykins! this is ripping [...] Have a drink?’ Quirister: ‘Well, with my old boy, I don’t mind if I do’.
1885		Bulletin (Sydney) 13 June 18/3: The old boy returned home late and found a yokel with a lantern under his kitchen window.
1890		Bulletin (Sydney) 12 July 12/2: His friend: ‘And so she refused you. Never mind, old boy, try again, perhaps you didn’t press her hand hard enough.’ / The rejected: ‘Press her hard enough – why she wouldn’t let me get near her.’.
1899		A. Binstead Houndsditch Day by Day 58: A good-natured, middle-aged old boy.
1914		H. Lawson ‘“I’ll Bide”’ in Roderick (1972) 827: The landlord was one of those little, fat, rounded-headed grey old boys.
1915		R. Lardner ‘Harmony’ in Coll. Short Stories (1941) 191: Keep it up, old boy. You got more than you ever had.
1923		Wodehouse Inimitable Jeeves 96: It would be a bit of a jar for the old boy.
1924		S. Scott Human Side of Crook and Convict Life 32: Pay the bill, old boy!
1937		E. Anderson Thieves Like Us (1999) 72: Pretty good for some old boys that didn’t have a pot or a window to throw it out.
1939		C. Himes ‘With Malice Toward None’ in Coll. Stories (1990) 53: Why, hello, Chick, old boy, I havent ’sen you in ages.
1943		R. Chandler Lady in the Lake (1952) 107: In a number of chairs old boys were snoozing peacefully.
1946		S. Jackson Indiscreet Guide to Soho 47: Congratulations, old boy.
1954		K. Amis letter 1 Dec. in Leader (2000) 414: Whacko, old boy. It’s very good of you both to do this.
1954		Wodehouse Jeeves and the Feudal Spirit 72: Poor old boy, how he does suffer on these occasions.
1963		(con. 1944) L. Glassop Rats in New Guinea 17: After all, old boy, there is a code.
1963		H.E. Bates Oh! To be in England (1985) 345: In an unguarded moment he actually addressed Pop as ‘old boy’.
1972		P. Fordham Inside the Und. 29: It is an education to walk through Mayfair or Belgravia with one of the old boys.
1973		Sun. Times Mag. 7 Oct. 46: You use people, old boy, not machines.
1993		I. Welsh Trainspotting 127: Rents’s auld boy’s [...] no really intae this sortay gig.
1997		(con. 1960s) A. Frewin London Blues 141: ‘Is there anything about her I shouldn’t know, Stephen?’ ‘Search me, old boy.’.
2000		Indep. on Sun. Rev. 21 May 57: Winterstoke is 80, tall and thin, with boyish-blue old-boy eyes.
2001		I. Welsh Glue 54: Dozo’s old boy bein a big gangster or crook or whatever the fuck eh’s meant tae be.
2013		T. Black Ringer [ebook] n.p.: The Old Boy would’ve been proud to see the job I’d done on this bint.
2015		N. Cummins Tales of the Honey Badger [ebook] I worked for the old boy doing landscaping.

2. (US/Irish) constr. with the, the Devil.

1782		in P. Freneau Poems (1976) 216: ’Till they all get as black as they paint the old boy [DARE].
1802		Balance 14 Oct. 317: The devil has been nick-named the old boy, perhaps by some as sounding more modish, familiar, or polite, and not bearing so hard upon him as his proper name .... His impudence in lying proves him to be an old boy.
1833		J.K. Paulding Banks of the Ohio iii 65: They keep more honest men from heaven than the old boy himself.
1858		Yale Literary Mag. xxiii 184: I have the pleasure of being the Old Boy, at your service.
1903		G.D. Chase ‘Cape Cod Dialect’ in DN II:v 298: Harry, n. In expression ‘ Old Harry,’ a rough-looking-strange man. ‘Old Harrry’s come now.’ As exclamations are used The Old Boy! The Old Boy Satan! The Old Boy Divle!
1909		P.A. Sheehan Blindness of Dr. Gray n.p.: The ould boy must have something to say to you, you blagard [BS].
1939		P.G. Brewster ‘Folk “Sayings” From Indiana’ in AS XIV:4 268: The following terms referring to the Devil: ‘the Old Boy,’ ‘old Hairy,’ ‘the Old Scratch,’ ‘old Nick,’ ‘the booger (bogie) man,’ ‘the Bad Man,’ ‘the Black Man,’ and ‘old Ned’.

3. the stuffing, the ‘daylights’, e.g. I’ll knock the Old Boy out of him.

1864

A.F. Hill Our Boys 40: J-j-just you try reportin’ me, and I’ll kn-kn-knock the old be-be-boy out o’ you .

4. (also old chap) the penis [boy, the n.¹ (1)].

1833		‘Black Sam’ in Out-and-Outer in Spedding & Watt (eds) Bawdy Songbooks (2011) IV 142: The next morn when I opened my eyes, / Then the Pavier no more could he stand, / So I drew my arm over his thighs, / To assist the old chap with my hand.
1927		in G. Legman Limerick (1953) 22: An afternoon of joy / Is hell on the old boy.
c.1935		‘Mae West in “The Hip Flipper”’ [comic strip] in B. Adelman Tijuana Bibles (1997) 99: You’ve just sunk the old boy right up to the nuts.
c.1940		in E. Cray Erotic Muse (1992) 385: Monday, I touched her on the ankle. / Tuesday, I touched her on the knee. / Wednesday—success! I undid her dress. / And Thursday her chemise, gor blimey! / Friday, I put my hand upon it. / Saturday, she gave me balls a tweak. Woo-woo! / And on Sunday after supper, I shoved the old boy up her.
1974		R. Blount Jr About Three Bricks Shy of a Load 263: A part of the body that attracts considerable private speculation, but hardly any public, is the old boy.
1985		R.G. Barrett You Wouldn’t Be Dead for Quids (1989) 67: She gently took hold of Norton’s cock and started stroking it. Norton’s old boy wasn’t real keen on the idea at first.
a.1986		in E. Cray Erotic Muse (1992) 43: He laid her on the dewy grass, / And then he shoved the old boy up her ass.
1998		R.G. Barrett Goodoo Goodoo 79: A cute backside [...] going up and down on his rainbow-coloured old boy.
2005		Roger’s Profanisaurus in Viz Apr. 47: flog pocket n. The front flap of a pair of Y-fronts, useful when a fellow needs rapid access to his old chap.