In a thought-provoking discussion, Stephanie Dinkins, the Kusama Endowed Chair in the Art Department at Stony Brook University, explores the intricate relationship between art and artificial intelligence (AI). During her conversation, Dinkins reflects on her childhood experiences with technology, particularly her affinity for CB radios, which served as an early platform for communication and connection with strangers. Dinkins delves into her groundbreaking project, N'TOO, a family history chatbot designed to preserve personal narratives and explore the complexities of representation in AI. She emphasizes the importance of ensuring that AI systems authentically reflect the voices of marginalized communities, rather than perpetuating existing biases. Throughout the discussion, Dinkins articulates her commitment to creating art that facilitates dialogue and understanding, challenging the conventional boundaries of artistic expression. As the conversation unfolds, Dinkins considers the ethical implications of AI in the creative process. She warns against the danger of viewing historical figures through a reductive lens, advocating instead for a nuanced understanding of their legacies. Dinkins envisions a future where artists harness AI not merely as a tool but as a collaborator that can enhance the artistic journey while remaining mindful of the broader societal impacts. In a world increasingly mediated by technology, Dinkins highlights the need for artists to navigate the complexities of innovation responsibly, ensuring that their work contributes to a more inclusive and equitable cultural landscape. With her unique perspective, Stephanie Dinkins invites us to reconsider the intersection of art and AI, urging a collective examination of how these evolving technologies shape our understanding of identity, history, and creativity.