This paper examines the interconnections between the history of homelessness and the history of labour in Australia. Taking a purposeful broad scope, focusing on the nineteenth and early twentieth centuries, the paper explores the ways in which homelessness is central to the history of work and labour. Drawing on the mythology attached to the swag and swagmen in Australian popular culture as its starting point, this paper demonstrates the need to understand the diverse experiences and meanings of homelessness - across specific contexts and times - as connected to the shifting cultures and practices of work, and associated gender and race relations in Australia's settler colonial context.