This article follows the careers of two African drivers in social environments that circumscribed their movement and access to technology. It begins with Vincent Njovu, whose memoir, The First Driver of Tanganyika, describes the driver's ability to navigate racial hierarchies of movement and technology, including the unlikely circumstances in which he fell in love with an ideal colonial machine. It then explores post-colonial cultures of gender and modernization by using the unpublished memoirs of Hawa Ramadhani, a woman who used automotive skills learned among nuns in the 1940s to become Tanzania's most respected driver. Paired together, the life histories of these drivers challenge historical narratives in which movement and technology (roads and motor vehicles, in particular) are used to discuss Africa's marginalization and decline. Instead, they show how transgressive practices of mobility can be used to challenge social and political orders and inspire new ways to think and act at uncertain historical junctures. Roads in these narratives are defined less by their danger than by their potential to turn unlikely individuals into heroes. Copyright © International African Institute 2013.