In the last two decades, shortcomings brought on by the crises of neoliberalism have pushed Latin American circus artists to reclaim the streets as their stage and to engage in transnational circulations. Based on an investigation conducted in Chile between 2016 and 2019, this article delves into the moral ambivalence that arises in the street circus activity from the intertwining of artistic, political, and economic motivations, with circus being seen as a way of criticizing dominant stances and order as well as a “good” way of earning one’s life in the Global South. The contradictions raised are analysed through the concepts of “artist critique” (Eve Chiapello and Luc Boltanski) and of “neoliberal reason” (Veronica Gago), showing how street circus challenges some oppositions that structure most of the art worlds, by reconfiguring the sense of critic and the economic necessities.