As more societies around the globe will have to reduce the dominance of motorized transport for more sustainable mobilities, masculinity studies has much to contribute towards engaging more fully with mobility and transport issues, not least the many ways in which technologies of movement relate to men, masculinities and (un)sustainable transport futures. Against this background, the chapter begins with a brief note on gendered mobilities and transport more generally, then moves on to discuss the connections between men, masculinity and automobility, followed by a section that focuses on driving, emotions and risk-taking. The chapter ends with a discussion on the implications of a transport future populated with increasingly automated vehicles, including what the implications for men and masculinities may be.