The socio-legal technology of licensing is one of the primary tools governments use to manage spaces and practices deemed risky or threatening to public order. Licensing requirements thus play a crucial role in shaping routine experiences in public space as well as the trajectories of emerging forms of public life. Yet licensing laws have largely been ignored in critical urban scholarship: too often concerned with the interpretation and critique of popular practices and public spaces, the mundane operations of urban governance are often left to practitioners and policy researchers. This article demonstrates how paying closer attention to licensure can provide valuable and unexpected insights into matters of social equality, urban amenity and economic opportunity. It does so through a comparative inquiry into practices of street food vending in New York City, Seattle, and Portland, Oregon. Drawing on ethnographic study and interviews, the article demonstrates how licensing can be involved in the production of quite peculiar and unjust geographies of practice, but also how shifts in popular culture can force a reconsideration of taken-for- granted laws. In conclusion, it is argued that a focus on licensing offers a productive pathway for new forms of critical urban research and provides a potential point of leverage in efforts to configure better and more democratic forms of urban public life.