This study employs narrative in order to examine circumstances wherein identity constructs and self-image are reconstituted in the face of oppressive circumstances. The authors of this article, both art educators/academics, explore the role of narrative processes at the intersection of an "art education of place" purposed to reinterpret extant lifeworlds and mediate premature identity foreclosures. Narrative methods open portals for the authors to express both the challenges and the merit of reconciling our identities as African American males and professional educators who navigate predominantly White institutions. In this article, we juxtapose two selected life episodes narrated in order to examine the spaces between iterations of our lifeworlds; our situational, relational, and oppositional responses to various oppressive conditions; and our navigation of the stigmas and stressors inherent therein. These stories and their analysis are presented as an exemplar of the mediation of contemporary identity and the potential of such mediations as a transgressive form of pedagogy and a significant redress to persistent popular culture mythologies about race and class.