Cádiz is a city in the southernmost region of Andalucía (Spain) famous for its annual carnival in February—a time when Cádiz’ historical center undergoes a radical transformation. Each year various groups of friends, neighbors, and colleagues create costumes, lyrics, and music independently from officially programmed acts. These “illegal” street performers—or carnavalescas callejera —create original comical acts based on recurrent themes and rhythms that come to life as they directly interact with thousands of people throughout all hours of the day and night. We use ethnographic data to examine the aesthetic, socio-political, economic, and symbolic dimensions of these massive street performances. Carnavalescas callejeras orally transmit social satires and ingenious political transgression based on sociocultural references that are very much anchored in local memory and identity. In this respect, we also reflect upon the significance of this massive performance as citizens autonomously transform urban spaces through their words and actions. As we argue, performers and carnival-goers partake in a singular ritual that contests social order, ridicules what is “politically correct,” and resists homogenizing cultural trends by affirming their identity.