A leader’s deliberate use of adaptive (positive) humor is a very powerful leadership tool. Research strongly suggests that humor can produce tangible benefits in the emotional, cognitive, and social contexts. It also suggests that the positive use of humor in the workplace can increase employee morale, improve communication, relieve tension, reduce stress, and increase team cohesiveness. Despite these benefits, the idea of humor is absent from current Army leadership doctrine and the idea of humor as an element of leadership is frequently dismissed as incompatible with organizational culture, purpose, and productivity and even irresponsible. This paper explores this topic through a literature review, presentation of historic examples, examination of the Army’s long and complex relationship with humor, and a review of previous Army leadership doctrine. This paper concludes with a recommendation to increase leader awareness and foster a deeper understanding of humor as an effective leadership tool.