We describe a collaboration between an artist, a mathematician, and a biologist, which examines the potential of drawing for understanding biological process. As a case study, it considers C. H. Waddington’s powerful visual representation of the “epigenetic landscape,” whose purpose it is to unify research in genetics, embryology, and evolutionary biology. We explore the strengths, but also the limitations of Waddington’s landscape and attempt to transcend the latter through a collaborative series of exploratory images. Through careful description of this drawing process, we touch on the epistemological consequences it had on all participants, artist and scientist alike.