In 1941 Ernestine Hill published My Love Must Wait, a biographical novel based on the life of navigator Matthew Flinders. In the same year, Eleanor Dark published The Timeless Land, imagining the arrival of European settlers in the Sydney region from the perspectives of multiple historical figures. In this article we examine how each author represents the important figure of Bennelong, a man of the Wangal people who was kidnapped by Governor Phillip and who later travelled to England with him. While both works can be criticized as essentialist, paternalist or racist, there are significant differences in the ways each author portrays him. We argue that Dark’s decision to narrate some of her novel from the point of view of Bennelong and other Indigenous people enabled different understandings of Australian history for both historians and fiction writers. Dark’s “imaginative leap”, as critic Tom Griffiths has termed it, catalysed a new way of thinking about the 1788 invasion and early decades of the colonization of Australia. The unfinished cultural work undertaken by these novels continues today, as demonstrated by subsequent Australian novels which revisit encounters between Indigenous inhabitants and European colonists, including Thomas Keneally’s The Chant of Jimmie Blacksmith (1972), Richard Flanagan’s Wanting (2008), and Rohan Wilson’s The Roving Party (2011). Like Dark, these authors situate parts of their novels within the consciousness of Indigenous figures from the historical record. We analyse the diverse challenges and possibilities presented by these literary heirs of Eleanor Dark.