Leadership theory routinely focuses on the relationships of leaders within the context of the work environment; however, culture and, specifically, films are a pervasive influence on both individuals and work environments. The literature review revealed that the relationships between higher-education faculty and administrators are strained. A conceptual framework known as the dark side phenomenon identified three dynamics affecting the work between faculty and administration: working relationships, supervisory roles, and the cultural impact. This lead to the research question: How are higher-education administrators portrayed as characters in popular American films? Data collection began with the selection of American films to study and involved four criteria: release of the film in the United States, inclusion of higher education in the film, a high level of viewership, and the substantial portrayal of a higher-education administrator within the film. The theoretical framework for data collection included Kenneth Burke's (1969) pentadic analysis and parts of George Gerbner's (1998) cultivation analysis. The data analysis identified that leadership behaviors are portrayed negatively in all but a few instances. Five major themes of negative leadership were identified: serving oneself, expelling undesirables, promoting prestige, finding money, and adhering to rules. Recommendations for leaders in higher education to mitigate the influence of negative film portrayals and suggestions for improving the quality of leadership were offered. Suggestions for further study include how film portrayal of higher-education administrators affects audience members, how the gender of administrators is portrayed in films, and how an institution's name is used in films. The study concludes by discussing the power of films, the need for media literacy, and the acknowledgement that the dark side of higher-education leadership can be mitigated by thoughtful, positive leadership behaviors. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]