In 1793, the artist Thomas Watling wrote to his aunt in Scotland and described his unhappy experience of living in the colony of New South Wales.1 As a disgruntled convict, Watling was far from impressed with his new surroundings; little escaped his diatribe, from the dull landscape to the unfair policies of the Governor. While Watling’s words are cheerless and dismissive of the fledgling community at Sydney Cove, they still offer us tantalising insights into colonial life, particularly regarding the colonisers’ interactions with the local inhabitants. When Watling writes about the ‘hours’ that the ‘natives’ would sit with him and watch him work, he conjures up an intriguing scene of people from vastly different worlds sitting calmly together and observing each other. Watling noted that it is ‘no small compliment’ to the art of painting that it is found in different countries, observing that ‘several rocks round us have outr e figures engraven in them’.2 But such glimpses fuel further questions: Who were these Aborigines? Why were they so fascinated by Watling’s work? Could these moments of contact have changed the relationship between people who were of such different cultural backgrounds? This article analyses the portraits of Aborigines produced by artists working in Australia during the first two decades of the European settlement of New South Wales, concentrating on the period from 1788 through to the start of the nineteenth century. The images are examined in relation to European colonisation and Enlightenment thinking, as well as via an attempt to gauge the perspective of the sitters. The study is limited to portraits (as opposed representations of a ‘type’, or unnamed, anonymous, generic figures), because portraits inherently involve negotiation between the artist and sitter, and the nature of this exchange is the focus of this study. The portrait is analysed as a relic of encounter, an object that has survived historical vagaries and is the product of a particular meeting at a particular time.