This paper presents the story of Pinocchio, considered in terms of its inherent ambiguity, combining some of the diverse representations of Pinocchio and Geppetto that reside in the history of film, print, literature and visual culture. While the subject of the inanimate object breathing life remains a favourite subject within all art disciplines; a key distinction in this paper is the connection of Pinocchio to 19th Century painting. The chapter looks closely at the enduring fascination of the Pinocchio story – how this centres on Collodi’s integral disruption of Pinocchio’s situation. Central to this portrayal is the way in which the writing of Collodi’s story can be associated with the subject of contemporary painting as a potential mode...