In this paper, I invoke Kwaku Anansi, the Ashanti-Akan trickster god embedded in oral traditions of storytelling in a living dialectic of survival and inversion across the African diaspora. This paper is about my meditation on painting and sculpture as a space fused with orality and writing. Anansi’s migration from Ghanaian oral tradition to Jamaican patois, Surinamese Sranan, and global pop culture opens significant questions on collaboration and storytelling which I explore here.