This thesis examines issues related to agency, playfulness, and behavioral design in robotic art. Using the term ‘whimsical bodies’ (inspired by artist Steve Daniels’, Whimsy, 2008) as an evocative metaphor for the playful ecology and creations of robotic art, I take up historical and contemporary case studies as entry points to a multi-faceted discussion of human-machine engagements considering the lenses of philosophical, art historical and curatorial methodological research. Robotic art’s whimsical bodies are also explored through references to new media scholarship, object-oriented-philosophy, metaphysics and speculative theory. In assessing characteristic features of the art form, such as its playfulness, use of humor, and critique/reconfiguration of wonder as a mode of critical engagement, this thesis aims to move robotic art from the periphery to the center of new media art as a lively and unique field of research.