As leaders in education and organization development, we should constantly look for new ways/techniques to understand human behavior, both individually and collectively. This paper/presentation provides an explanation of how the film "The Green Mile" can be used to understand Hall's (Human Development Model & Styles of Leadership, HDM, an essential model for understanding leadership, human/organizational development, and individual/organizational transcendence. Highlights of this paper/presentation, as seen through an analysis of the journey of the characters in "The Green Mile", are as follows: 1) "leadership" can occur from almost any set of circumstances, and is derived less from "doing" and more from "being"; 2) individuals can only "transcend" one level at a time, and good leadership is able to move up and down the various levels, as the occasion requires; and 3) the highest levels of Hall's HDM are most likely only attainable from a spiritual refinement of one's inner journey. These are key learnings for educators and practitioners alike.