This thesis contributes to the growing scholarly interest in connections with Australia's past through localised, individual stories. While much of this scholarship has focused on literature and the writings of cultural historians, this thesis concentrates on ways of visually recovering the memory of historical figures in relation to land through examining a unique form of portraiture which I have termed 'imagined'. The concept of imagined portraiture is distinguished from more conventional modes of portraiture using analyses of traditional portraiture by Richard Brilliant, Omar Calabrese and Catherine Soussloff. Imagined portraits, as I have defined them in my thesis, result from a temporal separation between subject and artist and involve a high degree of projection of the artist's self in portraying the absent subject. In contrast to naturalistic posthumous portraits which suppress the artist's identity as maker of the image to preserve external likeness, imagined portraits reflect the persona of the artist as much as the subject of the portrait. This thesis is structured around imagined portraits by five Australian artists: Sidney Nolan's paintings of Ned Kelly, John Lendis's paintings of Lady Jane Franklin, Anne Ferran's photographic portrayals of female convicts, Leah King-Smith's photo-compositions of Victorian Aboriginal people, and Julie Dowling's paintings of her ancestors. In all of the artworks under consideration person and place are intimately bound and inseparably recalled. Land is central to the identity of the subjects, but it is also important to each artist's own relationship between self and place.The artists studied in this thesis bond with historical figures to connect with Australia's past and form, or repair, meaningful attachments to the land. Using an interdisciplinary approach, I draw on the theoretical writings of philosophers Edward Casey and Jeff Malpas, historian Peter Read and feminist scholar on race and gender issues bell hooks to contend that knowledge of the past is critical to constructions of place and identity. Due to the imaginative nature of the portrayal of the figures and the fusion with land, many of the featured artworks have not previously been considered portraits. Doing so enables a fresh perspective which highlights that an individual who actually existed lies at the core of each image. I argue that this is crucial to the artwork's capacity to arouse empathy with current-day viewers ‚Äö- something that is underscored by theorists of historical fiction, such as Herbert Butterfield, Georg Luk‚àö¬8cs and Jerome de Groot. The historical subjects portrayed in this thesis are outsiders, many of whom have a troubled place in mainstream Australian history. Imagined portraits activate remembrance of these figures. They can contribute to the memory of those already mythicised, or recover individuals who were previously marginalised or excluded from Australian history. The imagined portraits featured in this thesis expose historical myths, gaps and silences while providing meaningful ways to connect with the past and negotiate displacement.