In the last decade, we have seen the rise of urban play as a tool for community building, and city-making and Western society is actively focusing on play/playfulness and intelligent systems as a way to approach complex challenges and emergent situations. In this paper, we aim to initiate a dialogue between game scholars and architects. Like many creative professions, we believe that the architectural practice may benefit significantly from having more design methodologies at hand, thus improving lateral thinking. We aim at providing new conceptual and operative tools to discuss and reflect on how games and smart systems facilitate long-term the shift from the Smart Cities to the Playable one, where citizens/players have the opportunity to hack the city and use the smart city’s data and digital technology for their purposes to reactivate the urban environment.