Cunningham traces a career built on relational serendipity and disciplined attention rather than formal training. He contrasts bureaucratic writing—like Hurricane Sandy rehabilitation requests—with creative criticism, emphasizing how reading reviews shaped his understanding of theater more than live attendance. His mission is democratic: making performance accessible to non-specialist audiences. He champions post-pandemic theater that prioritizes inclusivity and systemic support, especially for voices like Jeremy O. Harris. Deep observation—whether at NBA games or art exhibitions—fuels his writing, which treats profiles as critical acts, not just biographies. He values editorial trust, citing long-term collaboration with editors like David Hagland that enables sustained exploration of cultural lineages, from Redd Foxx to Tracy Morgan. Rejecting reductive labels, he writes about Black artists with intellectual rigor and personal investment, grounding all work in voracious reading, self-reflection, and the joyful rigor of paying extreme attention.