Pop culture has served as a catalyst for leadership development, both creating and manufacturing culture while also creating the parameters for us to understand culture in a public context. While pop culture has influenced how people engage with leadership development across contexts, celebrities have been the manifestation of pop culture throughout history. Through the influences of socialization and the evolution of pop culture, the field of leadership development has been impacted in a myriad of ways. This article will explore pedagogical techniques that leadership educators can utilize in curricular and co-curricular learning environments and unique recommendations, implications, and applications across various contexts.