This thought-provoking collection of dialogues delves into the complexities of decolonization in Southern Africa, reimagining the concept of classics and shedding light on transformative pedagogies. Drawing on diverse voices and experiences, the book explores the histories and reinterpretations of African classics, as well as the challenges and triumphs of teaching and learning in this unique context. With a focus on southern Africa, this book offers a nuanced exploration of the region’s rich cultural heritage and the ongoing process of decolonization. Through four distinct dialogues, the authors engage with pressing questions and debates, avoiding simplistic answers and instead offering new insights and perspectives. By bringing together established and emerging voices, this book provides a rich tapestry of ideas and experiences that are relevant far beyond South Africa.