The UVM Art and AI Initiative is exploring approaches to artistic image production, comparing the results of StyleGAN and Genetic Algorithms. More broadly, the project explores emerging artistic practices with Machine Learning and AI while referencing an artistic lineage to the artists Wassily Kandinsky, Jonn Cage, and Yoko Ono; these artists employ(ed) instructions and systems in their non-digital artworks. Kandinsky distinguished systems and developed a science of aesthetics with the basic elements of point, line, and plane; Cage used the oracle ‘I Ching’ like a computer to inform his compositional decisions; Ono writes poetic scores that turn her audience into active participants when they follow a series of imaginative instructions. Through their research and practice, the team seeks to join the larger conversation about art and A.I.