Popular culture exists as an expression of cultural history. It speaks to who we are, what we aspire toward, and where our generation stands in relation to the major issues of the day. This article is a conversation about the myriad perspectives offered in this issue of "New Directions for Student Leadership," exploring the contributions each makes to the study of leadership and leadership development, engages with popular culture as an important tool in leadership education and development, and explores some of the limitations that have risen with using popular culture, regardless of the form used. Furthermore, the conversation will explore how a leadership pedagogy, rooted in popular culture, has the potential to serve as a transgressional space, creating a place where the voices of the marginalized and minoritized might be heard and better understood.