Time Out Sydney

Take Time Out's walk on the wild side with these dirty dozen 'no-spots' in Underbelly-land...

Underbelly map

1. Plunkett Street, Woolloomooloo

Home to the ‘Plunkett Street Push', a gang of juvenile delinquents who brawled using sand-filled socks and blades with rival gangs such as ‘Surry Hills's Forty Thieves' and the ‘Ultimo Big Seven' - often merely for beer and tobacco.

Raise... a cuppa to black magic at Toby's Estate Coffee & Tea. Cathedral St.

2. Cathedral Street, Woolloomooloo

Tilly Devine's favourite beat as a working girl, this unholy strip was also where pimp, gunman and leader of the Darlinghurst Push, Guido Caletti sliced and diced citizen Jules De Flyn in October 1927.

Raise... your spirits with a spirit at the blessedly pokie-free East Sydney Hotel. Cnr Crown & Cathedral Sts.

3. 2 Lansdowne Street, Surry Hills

Kate Leigh's lair. Her bodyguard (and sometime lover) Henry ‘Jack' Baker was shot twice here by gunman ‘Chow' Hayes on 19 Feb 1938. Leigh and her henchmen tossed presents to the urchins of Surry Hills from the upstairs balcony every Christmas.

Graze... on Italian cuisine's greatest hits at Caffe Sicilia. Crown St.

4. 212 Devonshire Street, Surry Hills

Of over 20 sly groggeries owned by Kate Leigh, three were on Devonshire Street and the biggest of them ("Mum's") stood at 212. Leigh lived in a tiny one-room apartment above this block until her death in 1964.

Raise... a shandy with your schnitty at the Shakespeare Hotel's killer drinks den upstairs. Devonshire St.

5. 99 William St, Darlinghurst

Razor-era Sydney was "an Alsatia for the criminal, the unfortunate and very poor". So it was in 1931 when Frank ‘the Little Gunman' Green (with Tilly Devine's husband ‘Big Jim' as accomplice) blasted Barney Dalton to oblivion here in 1931 - payback for the Leigh-ordered shooting of Green months before.

Raise... a bevy to Barney at wine bar Love Tilly Devine. Crown Ln, Darlinghurst.

6. 104 Riley Street, Surry Hills

Kate Leigh shot and killed "Snowy" Prendergast here on 27 March 1930. The next year she gunned down Joseph McNamara. Her luck ran out in 1931 - busted with cocaine by Sydney's most famous policewoman, Lillian May Armfield.

Raise... a $3.50 schooner at the Porterhouse, once the Razor-era Dimitri's Five Doors tavern (named for its escape routes). Riley St, Surry Hills.

7. Charlotte Lane, Sydney

Norm Bruhn, leader of the original razor gang, was bugled to Jesus here in 1927, gunned down outside Mack's, a sleazy cocaine and sly-grog den he'd robbed days earlier. Bruhn's bulleting was inevitable after he'd robbed and raided Tilly Devine-owned brothels, assaulting prostitutes and patrons alike.

Graze... at Bill and Toni's for bloody good bolognaise. Stanley St.

8. Cnr William & Forbes Streets, Kings Cross

The 50/50 was Sydney's most iniquitous drug and illegal liquor den, where "thugs, half-castes and painted women of the street mingled with well-known scions of society". Pick-pocketing, fisticuffs and extortion were rife.

Raise... a cup at Ten Buck Alley (named for the nearby street where "anything's yours for a price"), a café where the coffee - like Razor-day revenge - is best served cold. Bourke St, East Sydney.

9. Eaton Avenue, Kings Cross

Site of the ‘Battle of Blood Alley'. When the Woolloomooloo Push realised Phil ‘The Jew' Jeffs was charging high for low-grade cocaine cut with boracic acid, biff was imminent. At 10pm on 7 May 1929 two heavily armed mobs met in this dim lane off Bayswater Road and for a hair-raising half hour went at it with guns, razors and clubs.

Raise... a mug of Ducale coffee at the café-cum-office for Richard Roxburgh's character in Rake. Piccolo Bar, Roslyn St.

10. Kellett Street, Kings Cross

On 9 August 1929, gangs loyal to Kate Leigh and Tilly Devine fought a pitched battle with guns and knives here, leading to a series of legislative crackdowns including the Consorting Act, which made it illegal for a felon to be in the company of other felons.

Gaze... into the eyes of a lover (or enemy) at Melt, a bar of whispers and dark corners. Kellett St.

11. 191 Palmer Street, Darlinghurst

Tilly Devine's brothel was the scene of wild parties, bloody shootings, Devine's 1945 wedding to Eric Parsons (and her shooting of him the same year) and, ahem, much horizontal refreshment.

Raise... a toast at bloodhouse Tradesman's Arms - now the swish East Village Hotel. 234 Palmer St.

12. Frog Hollow, Cnr Riley & Albion Streets

This pit was once the most vice-filled acre in the Commonwealth. Flimsy tenements piled on top of each other were home to gambling, drug dealing, prostitution and the movement of stolen goods. In 2007 it was reclaimed by the city as public parkland.

Raise... merry (yet responsible) hell with the Green Fairy at Absinthe Salon. 87 Albion St.

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Updated on 5 Jun 2015.

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