The discourse on the use of film in the educational leadership classroom is often limited to the viewing of Hollywood features or industry films created specifically for training purposes. The authors were motivated by an interest in finding new, valuable curriculum material and mediums that can inform and transform the work of education administrators. Guiding the selection of films are the vision of leadership as defined by the New Democratic Ethical Educational Leadership (New DEEL) and the Multiple Ethical Paradigms (Shapiro & Stefkovich 2005). This paper discusses five documentary films for use with educational leaders to enhance course curricula.