This article places race at the analytical center of a comparative urban transport history of early twentieth-century Singapore and Manila. It focuses on motorization, as seen in the influx and eventual dominance of streetcars and automobiles. The British and the American colonizers turned these Western-made vehicles into symbols of colonial modernity, defined in racialized terms. They regarded the different “Asiatics” as naturally ill-equipped to handle streetcars and automobiles, and when the colonized proved them wrong, the colonizers framed these acts using the racialist discourse of “potentiality.” Nevertheless, the native transport laborers appropriated motorized vehicles in ways that the colonizers did not imagine. Machines presented the natives a world of knowledge, which was maximized for financial gain. The acquisition of various forms of knowledge thus revealed a paradox of the civilizing mission: the colonizers exposed natives to the world of civilized knowledge, but the acquisition of this knowledge disrupted colonial discipline.