Tough Nuts: Australia's Hardest Criminals - Season 2 (2011)

Tilly was a drug dealing brothel madam, a criminal sociopath and Sydney's Queen of vice, who clawed her way to the top of the city's sex trade with a razor in her hand. Tilly Devine was a prostitute who founded a criminal empire on the mean streets of Sydney after the First World War.

Criminal lunatic, gunman, arch-thief and armed robber, Jockey Smith terrorized Australia at gunpoint for three decades. When confronted, the short angry guy with a bad case of small man syndrome invariably reached for a gun.

Multiple murderer, drug dealer, kidnapper, extortionist and street hoon, Dino Dibra grew up in Sunshine - a tough working class suburb where he became lifelong friends with a group of boys at school who would all go on to make their marks in Melbourne's underworld.

Multiple murderer, extortionist, pimp, child killer and violent thug, Regan is arguably the most violent and terrifying person in Australian criminal history. A genuine psychopath, Regan spent his childhood in rural New South Wales torturing animals.

Murderer, standover man, race fixer, SP bookmaker and crime lord, George Freeman was the King of Sydney for over three decades. His skills as a gambler and race fixer meant he could enrich his associates and a growing band of influential people who helped keep him out of trouble with police.