In this episode, we hear a conversation between abstract painter Lisa Corinne Davis and Richard Mayhew, a luminary landscape painter, who, at 98, is still painting every day. They discuss their respective approaches to painting, their use of color, and how they address internal and intellectual “subjects” with their painting. They also talk about how they became artists and the roles that their families played in their development. Richard tells us about his Shinnecock grandmother’s support of his early artistic work and how this heritage influenced his art making. He regales us with stories about his influences from Toni Morrison to his peers in the Spiral collective and sculptor Augusta Savage. Lisa and Richard relate to each other as interdisciplinary educators and share their experiences with how their progressive approaches to arts education were received with some resistance at times. Interesting connections between the two painters emerge throughout the conversation despite being from different generations as they discuss important centers of Black American artistic practice over the years. Both discuss the honor of being elected by their peers as National Academicians and how their inductions are separated by nearly 50 years.