Green’s Dictionary of Slang

1. (orig. US) to go on a spree; ad hoc vars. and extrapolations abound.

1865		letter q. in Wiley Life of Johnny Reb (1943) 66: We [...] visit the Theaters may be get on a big Whope & Paint the thing red.
1878		Oracle XII 28: And nightly I painted, Vermillion, the town; / Or with flashes of crimson, I varied the hue, / While language Soph’moric, Would make the air blue.
1884		Wheeling Dly Intelligencer (WV) 24 Sept. 3/3: The boys painted the town a ‘bright vermillion’.
1884		Caldwell Journal 16 Oct. in Miller & Snell Why the West was Wild 515: A pair of very ‘fly’ Chicago drummers came down last week bent on doing the ‘boys’ up and painting the town red.
1885		Bulletin (Sydney) 23 May 14/1: Great sport up in Newcastle (N.S.W.) steam-tug racing. The local Marine Board, however, do not encourage sport, and threaten to deal severely with any tug-master who takes to ‘painting her red’ in future.
1887		F. Francis Jr Saddle and Mocassin 147: One of these chaps from Texas come in there to paint the town, and got his tank full.
1887		‘’Arry on the Jubilee’ in Punch 25 June 305/1: The town’s painted red, I can tell yer.
1887		Dallas Dly Herald (TX) 28 Jan. 1/2: They wore the garb of a veritable cowboy [...] who might paint the town vermillion hue if they got on a rampage.
1888		A. Trumble Mott Street Poker Club 33: ‘Mr Hong-Lung may be confidently expected to paint things red in his best style’.
1890		Sporting Times 8 Mar. 1/4: A party of Brighton viveurs drove over to Worthing a few days back, and no sooner struck the little town than they began to get in the decorating work with the carmine brush. By six o’clock the pretty little watering place was as red in the face as a spanked baby.
1890		Sporting Times 15 Mar. 3/5: It is utterly wrong to suppose that Wilfrid Lawsonites never ‘paint the town’.
1891		Sporting Times 17 Jan. 1/3: And the pair were painting the Tivoli pea green with the proceeds.
1894		Truth (Sydney) 30 Dec. 1/6: Young Crossbred, son of a big speculating Victoria squatter, ‘came in’ and painted the town red.
1894		Civil & Milit. Gaz. (Lahore) 27 Sept. 1/4: He must not paint the country red, nor go upon the spree.
1894		St Paul Dly Globe (MN) 24 June 9/3: When Coxey gets to Congress [...] we’ll paint the town vermillion just whenever we durn please.
1894		‘O. Henry’ ‘Chanson de Bohême’ in Rolling Stones (1913) 243: I’d rather distribute a coat of red / On the town with a wad of dough.
1894		Mirror of Life 24 Mar. 15/2: [H]e can devote a few evenings out painting the town a deep vermilion.
1895		W. Pett Ridge Minor Dialogues 263: We painted the bally place red, I can tell you. When we’re out on a randan, we don’t care a ---.
1895		C. Crowe Aus. Sl. Dict. 55: Paint the Town Red, to play a great lark.
1897		Melbourne Punch 25 Feb. 4/4: An’ he paints the district crimson when you get him fairly wild.
1900		Punch 17 Jan. 44/3: The cheerful royst’rer of uncertain tread, / Who used to paint the town bright red.
1901		Bateman & LeBrunn [perf. Marie Lloyd] Folkestone for the Day 🎵 We painted Folkestone beautiful red, and came back lovely brown.
1902		‘P. Luftig’ ‘Where are my Dollars Gone?’ in Bulletin Reciter 1880–1901 77: A trifle glorious I may get, now and then, with comrades gay, / And paint the town vermillion.
1904		Sydney Sportsman (Surry Hills, NSW) 30 Mar. 3/7: [A]fter he had painted London a bright carmine he was told he’d better cut it out.
1905		Sun. Times (Perth) 12 Mar. 4/7: A Perth architect, well known for his proneness for painting the town on occasions, gave the city an extra coating [...] last week.
1911		A. Bennett Card (1974) 125: As for setting the town on fire, or painting it scarlet, he seemed to have lost the trick of that.
1911		Dly Ardmoreite (OK) 2 Oct. 5/4: Smith proceeded to paint the town a bright vermillion [...] and to start a rough house at his home.
1914		Truth (Melbourne) 31 Jan. 7/4: The hobbledehoys [...] painting things very red and the gals on their part painting things a trifle blue.
1915		Wodehouse Psmith Journalist (1993) 173: One who, like myself, arrives with a brush and a little bucket of red paint, all eager for a treat.
1918		C.J. Dennis ‘The Joy Ride’ in Backblock Ballads 103: They ses we painted Fernville red; / They ses that we were gay.
1919		Noble Sissle ‘How Ya Gonna Keep ’Em Down on the Farm?’ 🎵 How ‘ya gonna keep them away from Broadway, / Jazzin’ around, /And paintin’ the town?
1920		Capt. Billy’s Whiz Bang Oct. 8: They were the days when we got paid together, painted the town together, and went broke together.
1922		S. Lewis Babbitt (1974) 192: Maybe the Babbitt men won’t paint that lil ole town red!
1925		‘Bartimeus’ ‘The Crusher’ in Great Security 151: ‘What are you going to do wirth all this money?’ [...] ‘Paint the town red.’.
1930		E. Glyn Flirt and Flapper 59: Flapper: [Making whoopee] means to paint the town red — kill time — go on a party — get stewed [...] run wild.
1936		‘Banjo’ Paterson Shearer’s Colt 22: We’ll race in Sydney, and then we’ll go to London later on and paint the place red.
1938		G. Kersh Night and the City 94: Red means having a good time, making whoopee: ‘Let’s paint the town red’.
1940		D. Maurer Big Con 74: He wants to got out and paint the town red.
1953		I. Hamilton Till Human Voices Wake Us 131: I’ve seen many playboys who’d paint the outfit a far deeper shade of red than Cedric could.
1959		S. Bellow Henderson The Rain King 120: Let’s jump off the train and paint the town red.
1965		(con. 1930s) R. Wright Lawd Today 146: ‘Lawd, I’m going to paint the town red!’ he sang.
1967		J. Wynnum I’m a Jack, All Right 21: We ought to paint the town red tonight.
1976		D. Ireland Glass Canoe (1982) 193: I’ve painted the towns red, white and blue.
1981		J. Sullivan ‘Go West Young Man’ Only Fools and Horses [TV script] I’m going out – I’m gonna paint the town red.
1993		I.L. Allen City in Sl. (1995) 65: In another rural view, a trip to town often entailed going on a spree or painting the town red. The latter, first found in print in 1884, is of uncertain origin but seems to be of the Old West, recalling some form of violence, such as the red of flames or blood.
2000		Guardian G2 3 Feb. 16: What is the origin of the expression ‘to paint the town red?’.
2001		Bay Weekly Online 2-8 Feb. 🌐 It had been 30 years since the Big B had a world’s champion on the gridiron, so I guess the boosters were entitled to paint the town purple as horns blared and firecrackers crackled and people danced in the streets.
2015		‘Elvis Costello’ Unfaithful Music 157: By Runcorn, we were a gang, all for one and one for all, ready to paint the town red upon our arrival .

2. to vomit.

1963–74		B. Humphries Barry McKenzie [comic strip] in Complete Barry McKenzie (1988) 27: Beauty. We’ll be painting the old town red, today.
1999		Indep. on Sun. Culture 15 Aug. 1: The latest generation [...] painting the town red, missing the last bus home.