woolloomooloo, adj. — Green’s Dictionary of Slang

woolloomooloo adj.

[Woolloomooloo, a waterside suburb in Sydney]

(Aus.) rough, unsophisticated, thuggish; thus Woolloomooloo bushman, one who rides a horse badly; Woolloomooloo upper-cut, a kick to the groin.

1885		Bulletin (Sydney) 3 Jan. 11/1: After a desperate struggle, he traded away his fish for a glass of what is facetiously called ‘Woolloomooloo champagne’ [i.e. beer]. [Ibid.] 9 May 9/1: Phillips (in the piece, of course) is a well-bred idiot, in whose direction any Woolloomooloo larrikin would be justified in starting a paving-stone without stopping to ask questions.
1904		Sydney Sportsman (Surry Hills, NSW) 12 Oct. 6/2: Mike Williams, the ‘Woolloomooloo rules’ pug who got a cronk decision over our Arthur Cripps.
1910		Sun. Times (Perth) 11 Dec. 14/3: The common terms being placed in inverted commas as if they were the unique phrases of Woolloomooloo larrikins.
1912		Herbert Rule [song title] ‘Woolloomooloo.’.
1967		‘Whisper All Aussie Dict.’ in Kings Cross Whisper (Sydney) xliii 11/3: woolloomooloo upper-cut: A strategic boot in the groin.
1983		R. Aven-Bray Ridgey-Didge Oz Jack Lang 52: Woolloomooloo Cocktail Methylated spirit with cordial [...] Woolloomooloo Uppercut A kick in the testicles.
1985		R.G. Barrett You Wouldn’t Be Dead for Quids (1989) 46: Les swung his foot back and gave him a Woolloomooloo uppercut straight in the balls.

In compounds

Woolloomooloo bummer (n.)

(Aus.) a thug, a tough.

1901

Truth 17 Mar. 6/1: [T]he officials (one of whom is a ‘converted’ Woolloomooloo ‘bummer’) chuck them out into the street, half nude, with the remainder of their clothes after them.

Woolloomooloo rat (n.)

1. (Aus.) a thug, a tough.

1931		A.W. Upfield in Adocate (Burnie) 18 May 4/7: ‘You - you blank Woolloomooloo rat!’ Rainbow snarled .
1935		Newcastle Sun (NSW) 23 Oct. 7/6: Mr. Reid (Indignantly): You Woolloomooloo rat, crawl back to the underworld where you belong .

2. (Aus.) used neg. of humans, in fig. comparisons with the animal.

1931		Truth (Sydney) 22 Mar 3/2: Chide ran a fair race, and it shouldn’t be long before he is giving more cheek than a Woolloomooloo rat.
1933		Sydney Sportsman (Surry Hills, NSW) 14 Oct. 2/1: Another who’s due to give more cheek than a Woolloomooloo rat is Winrose.

woolloomooloo Yank (n.) (also King’s Cross Yank, Sydneyside Yankee, woolloomooloo Frenchman, woolloomooloo Yankee) [Yank n. (2)/SE Frenchman]

(Aus.) a relatively unsophisticated person who attempts to ape the supposedly more sophisticated style of an American or Frenchman.

1912		Truth (Sydney) 13 Oct. 9/8: Janie Smith is a prostitute, and keeps the house in which accused’s brother, at present lives. He had no lawful means of subsistence. He was well known by the name of ‘WOOLOOMOOLOO YANK’.
1914		Sun. Times (Perth) 29 Mar. 8/4: We might even tolerate the Woolloomooloo Yank who wears billowy trousers and says ‘sure!’ when he means ‘yes’.
1914		Sun. Times (Perth) 29 Mar. 8/4: Perhaps the most grievous bore in Australia at present is the Sydneyside yankee who talks through his smelling organ.
1916		Dungog Chron. (NSW) 28 July 3/2: An English exchange has lately published a list of Australian slang expressions. Most of them are quite new to Australians, but are reminiscent of some of the wild-beast expressions of the Wooloomooloo Yankees.
1929		Brisbane Courier 9 Mar. 8/5: The larrikin known as ‘Woolloomooloo Yank,’ who wished to see his men win at any cost.
1937		Courier mail (Brisbane) 25 Oct. 14/6: In Sydney they have the saying ‘A Woolloomooloo Yank’.
1947		Sun (Sydney) 18 May 3/6: On the [USN] flag ship Shangri-la, the crew have been studying the Australian language from a special slang glossary [...] A ‘Woolloomooloo Yank’ or a ‘Fitzroy Yank’ is described as a ‘flashy dresser’.
1963		Aus. Women’s Wkly 18 Sept. 15/6: I talk like a Woolloomooloo Yank but I’m an Aussie in my heart.
1984		V. Darroch On Coast 42: Woolloomooloo Yank: A name applied to any seaman of Australian origin who adopted an American accent.
2001		(con. 1945–6) P. Doyle Devil’s Jump (2008) 87: He was a ‘Kings Cross Yank’ – as Australian as me, probably, but he spoke with a fake American accent.