The profile of prisoners across many Western countries is strikingly similar 95% male, predominantly undereducated and underemployed, from the most deprived neighbourhoods. This book reflects on how similarly positioned men configure masculinities against global economic shifts that have seen the decimation of traditional, manual-heavy industry and with it the disruption of long-established relations of labour. Drawing on life history interviews and classical ethnography, the book charts a group of mens experiences pre, during and post prison. Tracking the development of masculinities from childhood to adulthood, across impoverished streets, failing schools and inadequate state care, the book questions whether this proved better preparation for serving prison time than working in their local, service-dominated, labour markets. It integrates theories of crime, geography, economics and masculinity to take into account structural and global economic shifts as well as individual long-term perspectives in order to provide a broad examination on pathways to prison and post prison.