In this chapter we present a way of understanding the role of culture, leadership, and schooling in Singapore from a sociopolitical perspective. We have consciously avoided using the well-known Hofstedeian framework as we believe that a sociopolitical perspective offers a richer detailing of culture in interaction with schooling. O ur argument is that “societal culture” in Singapore can usefully be understood as an evolving mix of what we term “traditional” and “modernizing” cultures, which are in turn complexly related to dominant political and economic processes. Notions of leadership, including school leadership, are a central strand in this discourse. A decentralization of the education system beginning in the mid-1980s is particularly significant for an understanding of recent developments in school leadership in Singapore. It opened up spaces for autonomous action in what had previously been a highly centralized education system. To illustrate our analysis we draw on a study of two improving government secondary schools in Singapore.