The near absence of Indigenous people in mid-nineteenth-century colonial painting has been one of the most potent assertions of continued settler presence in Australia. This invisibility reinforced the myth of terra nullius and rendered further colonial expansionism picturesque. Many colonial artists were reluctant to insinuate the original owners into the landscape, thereby avoiding complicated issues of dispossession, resistance and guilt. Remarkably, the oeuvre of Robert Dowling is distinguished by his depiction of Aboriginal people, not as background figures but as subjects, conspicuously interacting with Europeans, which opened up new mythologising possibilities. Robert Dowling’s commissioned portraits and history paintings of the nineteenth century engage with the Indigenous population, yet the resultant works cannot be innocent of the impact of colonisation in south-east Australia. Masters George, William, and Miss Harriet Ware with the Aborigine Jamie Ware (fig. 1), Tasmanian Aborigines (fig. 2) and Early effort – art in Australia (fig. 3) reflect Dowling’s sometimes didactic, ambiguous and oppositional views and his representations of Aboriginal people can be described as a move from apparent harmony to memorial and, finally, to unchallenged ascendancy.