Leadership scholar Margaret Wheatley (2006) observed that "Each of us seeks to discover a meaning to our life that is wholly and uniquely our own. We experience a deepening confidence that purpose has shaped our lives even as it moved invisibly in us. Whether we believe that we create this meaning for ourselves in a senseless world, or that it is offered to us by a purposeful universe, it is, after all, only meaning that we seek" (p. 134). At a small, private liberal arts institution in the southeast, educators attempt to traverse the complexities of chaos and meaning by integrating film into many facets of the curricular and co-curricular leadership learning process. This article highlights the background, pedagogy, and impacts of this integration and the bridge thus created between the in- and out-of-class experiences for students.