This chapter examines how lowly city dwellers confounded their purported benefactors, for example, by violating cardinal points of civility, indulging their appetites at taverns and brothels, or intruding into the exclusive spaces of the well-to-do. Many urban New Yorkers behaved in ways that were contrary to elite expectations and in so doing risked sanctions from those who controlled important resources. Poor people tended to transgress the rules set by gentlemen and engage in immoral behavior. In precarious circumstances, they perpetually did what was necessary to stay afloat, even if it meant flouting the Christian-based moral standards upheld by the elite. This chapter considers how people disdained as nonentities in eighteenth-century New York City, including blacks and prostitutes, contested the dominion of the city's gentlemen and thus diminished the elite's cultural authority.