This chapter addresses the development of Mediterranean island prehistory from Gordon Childe to John Evans's watershed papers, and charts the emergence of a comparative and explicitly quantitative island archaeology, heavily informed by biogeography, in the 1980s and 1990s. If the dominance of Childe's legacy into the 1960s explains the failure of an explicitly insular Mediterranean archaeology to emerge, then the breakdown of the diffusionist paradigm likewise played a decisive role in its development. The chapter outlines critiques of Mediterranean island archaeologies posed in the 1990s and 2000s. Essential to the development of maturity within Mediterranean island prehistory has been the recognition that many causal factors must be combined, in order to account for the development of island lifeways. The chapter also presents the practical and heuristic consequences of different paradigms, and suggests future areas of development in Mediterranean island prehistory using data from the period between the later Upper Palaeolithic and the Late Bronze Age.