This chapter discusses the 20th century street vending context, the major forces influencing how street vending has been interpreted and responded to in early 21st century cities and then, using a food truck controversy in Chicago and the regulation of second-line vending in New Orleans, the effects of the trends. Street vending has been a touchpoint for urban life stretching back to early cities that served as centers of trade and commerce. On the street, people exchanged goods, shared specialized knowledge, skills or services and exchanged information. In industrial cities, life unfolded on the streets. Prior to and in areas without refrigeration, iterant food vendors brought fresh food to urban neighborhoods. The situation in Guangzhou highlights a fundamental tension: Accepting street life can still mean creating a highly controlled environment or attempting to move it to undesirable spaces. The situation of street vending speaks to the shifting role of street cultures of living that take place on the street.