This paper examines the rapid expansion of São Paulo’s theater business between 1900 and 1916 and the reactions that this process incited within the city’s assembly halls. In doing so, I seek to understand the real and imagined function of business in the city’s cultural and social development. I begin by explaining the emergence of a Paulistano entertainment industry in three phases, tracing the diversification and then concentration in theater ownership and management. I then analyze discursive and legislative responses by the city’s civic leaders as they felt their grip on theaters weakening. I argue that in a society newly urban, the formation of a native entertainment industry posed a unique conundrum for its critics: on one hand, local business was encouraged in order to maintain economic growth, but on the other hand, commercial theaters were viewed by many as culturally corrupting and thus detrimental to a developing city. To diffuse this tension, Paulistanos increasingly turned to government regulation, in this manner setting the foundation for what would become Brazil’s first municipal Department of Culture and Recreation.