Most possibly the worst, most undeniably horrible place to be in Sydney. And it has a truly retarded name.
It exists just east of the Sydney CBD.
Contains nothing but a wide range of social problems. The kind that walk up, crown you with a block of wood and relieve you of your wallet, phone and other valuable possessions.
The Bureau of Crime and Statistics shows this area to have the highest concentration of general crime ( assault, robbery etc ) Statistically this place is worse to walk around in than Redfern.
"Shit man, what happened to you?"
"Ugh I was just in Woolloomooloo, Twelve Islanders just bashed me for my phone, then I got rolled by Abos and Lads, and then I was raped by a policeman."
by leftrightout January 10, 2008
woolloomooloo is where you wish you were grown up in and if you wasnt you say you were. its what all you fake lad cunt want to be... whydoubleyoubee

YWB 2011
fakelad1, "i wish i lived in woolloomooloo and was YWB"

fakelad2, "i do im in ywb you can put it up to"

O.G woolo boy, "no you dont your barred lads"
by the OG woolo boys 2011 August 10, 2008

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