Australia's Hardest Criminals Episode Rating Graph

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. She established a network of brothels, enslaved her working girls on cocaine and slashed, bashed and shot her way to the top of the criminal tree in Australia. Growing up as a child prostitute in London, Tilly met Jim Devine, an Australian soldier during World War One. Tilly arrived in Sydney as a war bride in 1920, only to find Jim putting her back on the game again. After five years working the streets, Tilly began building a network of brothels around the Palmer Street area of Woolloomooloo in inner city Sydney, with the violent drunken thug Jim as her partner. When the men reached for their cutthroat razors in gang fights, which proliferated in the 1920s, Tilly did the same, slashing the face of any man who got in her way. Her propensity for violence and the impulsive bursts of rage never left her and Tilly remained a sea of explosive anger to the day of her death in 1970. Tilly survived two World Wars and the Great Depression and became incredibly wealthy from the proceeds of her sex and drug empire. Like the gangster Al Capone, Tilly’s empire collapsed when she was pulled up by the Tax Office and handed a fine of 20,000 pounds. Tilly was forced to liquidate everything, and lost her empire overnight. By the time of her death in 1970, Tilly had become an embarrassment; an historical anomaly, a ghastly monster of a past that the people of Sydney no longer cared to dwell upon.

Brutal killer, armed robber, heart-breaker and prison escapologist, Ray was the ultimate anti-hero who spent his whole life running from the nightmares in his head. Denning’s cards were marked when he was just ten years of age. After many years of terrible domestic violence, his mother committed suicide in the family home by setting herself alight. Ray was found trying to quench the flames. With his teenage years spent on the streets and in and out of reformatories, Denning drifted into a life of crime. But whereas most boys his age were involved in petty theft or stealing cars, Ray Denning became an armed robber at 18 years of age. Caught by police and sentenced to 13 years in prison, Denning tried to escape from Parramatta Jail. During the escape attempt, Denning bashed a prison guard almost to death with a claw hammer. The prison guard, Willy Faber was so terribly wounded that he later died of his injuries, but as he died over a year after the attack Denning could never be charged with murder. Sent to Grafton Jail, one of the toughest prisons in Australia, Denning became politicised and started campaigning for prison reform. He also became the only man in history to escape from its walls. After his escape from Grafton Jail, he fled to Sydney where he conducted a high profile campaign for prison reform. Denning was a serial escapologist, who also escaped from Maitland and Goulburn Prisons, and spent over two decades in prison or on the run before stunning police and criminals alike when he rolled over to avoid a life in jail.

Meet Australia's most wanted man for a record 11 years. Russell 'Mad Dog' Cox was a man no prison could hold. He escaped from New South Wales' notorious 'electronic zoo', the maximum security Katingal jail - the jail the politicians had said was escape proof.

Arguably Australia's most feared gangster, Frederick 'Chow' Hayes was a convicted double murderer, sentenced to hang in 1952 for the brazen killing of standoverman and former boxer, Bobby Lee.

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. Freeman grew up on the tough streets of Annandale and fell into crime at an early age. A product of boys’ reformatories like Mt Penang in Gosford, Freeman was a small waif like child, and suffered the worst imaginable treatment. His response to the terrors of his childhood was a seething violence that remained with him until his middle years. Approached by Sydney’s Mr Big, Lennie McPherson, Freeman dropped his life of property crime and began concentrating on illegal gambling at McPherson’s behest. Freeman rapidly became one of Sydney’s most influential criminals, running a network of SP bookies and standing over the illegal casinos for protection money. Freeman, together with McPherson and Stan “The Man” Smith formed a criminal alliance known as The Team. While Freeman fronted as The Team’s gambling heavyweight, he was not above committing murder to entrench The Team’s dominance in the Sydney underworld. When the madman, Stewart John “The Magician” Regan loomed as a threat, it was Freeman and Tough Nut Stan ‘The Man’ Smith who did the shooting. A decade later, Freeman and Smith would join forces again, this time to dispatch the loose cannon, hit man, Christopher Dale “Rentakill” Flannery. In 1979 and at the height of his powers, Freeman faced an assassin’s bullet but lived to tell the tale and exact revenge. Muller had a grudge against Freeman, and shot him in the neck and face outside the front door of his mansion at Yowie Bay with .22 handgun. The gangster kingpin took a contract on Muller’s life, and within six weeks Muller was shot dead. In his dotage, Freeman, a chronic asthmatic, became addicted to pethidine, and the King of Sydney died prematurely as a result of his addiction.

Dennis Allen was the oldest son of Melbourne crime matriarch, Kath Pettingill. While the remainder of her sons are criminals and some of them vicious killers, not one comes close to the utter brutality of Dennis Allen.

Christopher Dale Flannery earned the nickname of 'Rent-a-kill'. He was a hit man and gun for hire who would kill anyone if the price was right. Find out about the man who killed in cold blood before returning to his home to smother his children with affection and dote after his wife, Kathleen.

Alphonse Gangitano was known as the Black Prince of Lygon Street and was the most lethal member of Melbourne's notorious Carlton Crew in the 1980s and 1990s. Through a series of re-enactments of the most significant events in Gangitano's life, relive the rise and fall of the Melbourne crime tsar.

Michael 'Melbourne Mick' Sayers was a run of the mill crook who got in too deep with some of the tough nuts in Sydney's organized crime scene. An associate and friend of Chris Flannery, Sayers ventured to Sydney and discovered that to survive on the mean streets, he had to turn his hand to drug dealing, extortion, race rigging and murder.

Raymond 'Ray Chuck' Bennett was Australia's criminal mastermind. A brazen armed robber and thief, he did the jobs that other criminals considered were beyond them. His most audacious robbery was The Great Bookie Robbery - a heist at the Australian Jockey Club while the bookies met to settle up from the weekend's trade.