The use of theory as a way of understanding urban life is explored in this chapter through a review of the research and practice literature. The need for a rethinking of theory to accommodate the evolving and increasing pervasiveness of artificial intelligence (AI) in urban life is surfaced. The review enabled formulation of a conceptual framework for urban life, theory, and AI to guide the explorations in this chapter and beyond. The evolving of theory on the one hand and the contesting of theory on the other hand may provide opportunities for creativity; prompting; unprompting, as in, spontaneous; and combinatorial outcomes. Employing an exploratory methodological approach, the theory of the city components of urban communication, attraction, and circulation are explored in relation to the challenges and opportunities of assemblage urbanism and city-making. This chapter provides an overview of insights emerging from the explorations pertaining to the rethinking, contesting, and evolving of theory in the context of AI environments, now and going forward, while acknowledging the presence of various limitations.