This chapter considers how Australian children’s and young adult literature published from the late twentieth century complicates early depictions of Anglo-Australian young people as uniquely connected with rural adventures and larrikinism through the exploration of urban Australian lives and multiculturalism. It pairs six novels as exemplars of three key moments of transition in Australian children’s literature in the past half century. First, it discusses Ivan Southall’s Josh (1971) as indicative of the abandonment of the bush as a central concern in the genre, situating it in relation to John Marsden’s Tomorrow, When the War Began (1993), which depicts rural Australia as under threat, rather than as a threat to children, as was typical in depictions of the bush in colonial children’s literature. Second, it examines the turn towards representations of ethnic diversity in Melina Marchetta’s Looking for Alibrandi (1992), a narrative of European assimilation, and Randa Abdel-Fattah’s Does My Head Look Big in This? (2005), which responded to post-9/11 anti-Islamic sentiment. Finally, it considers two novels published in 1998 that signal the long road to the depiction of fully realised Indigenous characters: Phillip Gwynne’s Deadly, Unna? (1998) and Melissa Lucashenko’s Killing Darcy (1998).