'The Wild Colonial Boy' is a traditional Irish/Australian ballad of which there are many different versions. It has been argued that the original version was really about Jack Donahoe (variously spelled Donahoo or Donahue), an Irish transport who arrived at Sydney Cove in 1825, and was subsequently convicted of highway robbery and sentenced to death. He escaped and waged a guerrilla war against the wealthy for more than two years in the country around Sydney. On September 1st 1830 he was ambushed by a police party near Cambelltown and shot dead, his companions Webber and Warmsley escaping into the bush. This version was eventually outlawed as seditious so the name of the protagonist changed.

The resulting Irish version is about a young emigrant, named Jack Duggan, who left the town of Castlemaine, County Kerry, Ireland, for Australia in the 1800s. According to the song (and in keeping with the true story of Jack Donahoe), he spent his time there 'robbing from the rich to feed the poor'. In the song, the protagonist is fatally wounded in an ambush when his heart is pierced by the bullet of Fitzroy.

The Australian version has Jack Doolan (or sometimes Jack Dowling) as the protagonist, and here Castlemaine refers to the Australian town in Victoria. In both versions variation in the wording and language occurs across different sources.

In his Old Bush Songs, Banjo Patterson wrote: "it will be noticed that the same chorus is sung to both 'The Wild Colonial Boy' and 'Bold Jack Donahoo'. Several versions of both songs were sent in, but the same chorus was always made to do duty for both songs." This chorus, included in some (not all) Australian versions is as follows:

Come, all my hearties,

we'll roam the mountains high,

Together we will plunder,

together we will die.

We'll wander over valleys,

and gallop over plains,

And we'll scorn to live in

slavery, bound down with iron chains.