This article discusses the application of Shulman's "signature pedagogies" through the utilization of films for preservice teachers and school leaders in Singapore. Using the films "Dead Poets Society" and "Ahead of the Class," this article explains how these films facilitated the participants' engagement with the surface, deep, and implicit structures of education. In the process, they applied critical thinking by arriving at criteria-based and context-appropriate judgments reflectively. The research findings reveal two broad themes. First, the educators were cognizant of the key issues, opportunities, constraints, and obstacles in teaching and school leadership. Second, they appreciated the importance of adopting situated teaching and leadership approaches to cater to the needs of various educational stakeholders. This study highlights critical thinking as a sociocultural practice where the educators (re)interpreted the films through their cultural lenses and drew on local resources and logics to deal with the challenges in teaching and the school contexts.