Largely unquestioned throughout the twentieth century, the connections between cars, mobility and notions of progress are beginning to unravel. This paper traces an argument that loosens the path dependence of automobility and hints at alternatives. It begins with a critical engagement of the burgeoning literature on hegemonic automobility to develop our analytical lenses of multiple automobilities and ecologies of the car. We then provide examples of two contemporary trends that try to reconstitute automobility. The first sees the major automotive companies attempt to re-position the car through advertising as an environmentally friendly mobility option. The second one, carsharing, poses more substantial challenges to hegemonic automobility through its re-imag(in)ing of the car. These examples, we conclude, highlight the complex possibilities of technology and culture coalescing to shape future forms of automobility.