The folk song The Wild Colonial Boy is known around the world and has been sung by artists as wide ranging as the Clancy brothers and Mick Jagger. Despite the popularity, very few know of the inspiration for the song: seventeen year old John Doolan. 

This mugshot is the first prison portrait of Doolan, a teenage tearaway who went on a spree of highway robbery with another teen, Ned Donnelly, in the early 1870s. Operating in the north of Victoria with the occasional jaunt into southern New South Wales, Doolan and Donnelly stuck up travellers on the highways for fun. Coming from a poor background, some could perhaps see that the poverty was a contributing factor in Doolan’s lawlessness, though Doolan demonstrated poor respect for authority and very little in the way of impulse control. 

Doolan stabbed a fellow apprentice during an altercation in 1869 and was imprisoned for one year. Doolan met Ned Donnelly on the prison hulk Sir Harry Smith and the two became instant friends. When Doolan completed his sentence, Donnelly absconded three months later to join him. 

Taking to the bush, the boys became a nuisance on the roads and stations around Huntley, stealing clothes and supplies. Their lawless days ended outside the Robin Hood Inn after stealing a spring cart. Chased down by troopers, the boys surrendered. 

When the boys were put on trial, their judge, Sir Edward Eyre Williams, decided to impose what he considered to be “deterrent” sentences. John Doolan received fourteen years while Ned Donnelly got seventeen. According to reports at the time, Doolan’s mother became hysterical at the sentencing given to her son. The harsh sentences were publicly denounced but Doolan stayed in prison until 1882 before vanishing from history. 

While the song was ostensibly about Doolan, the narrative includes parts of the careers of Harry Power and Jack Donohoe including Donohoe’s death during a gun battle. Despite the artistic license, the song has meant that Doolan remains a familiar name in the Australian “rogues gallery”.