This article focuses on teaching critical literacy in the context of Singapore. It begins with a conceptualization of critical literacy as a stance oriented to questioning and challenging the often taken-for-granted meanings and assumptions found in ‘everyday’ texts. It then discusses how this stance can be cultivated in students through a critical reading and writing project aimed at encouraging students to question the underlying motivations of seemingly unremarkable texts (‘making the familiar strange’) and produce alternative texts that challenge and destabilize the normative structures of society (‘making the strange familiar’). The article concludes with a brief discussion of the issues and challenges faced by teachers in developing a critical disposition in students that will help them negotiate the information-saturated and text-mediated world of the twenty-first century.