Robots, clowns and clown robots are pop cultural icons. Clown robots, whether funny or not, represent comic visions of a technological humanity and tap into our technology-related uncertainties and desires about how we embrace, tame and enhance our technological world and future. In popular entertainment, clowns and clown robots use technology for comic effect, or are comically created by technology. But if clowns and robots are popular icons, and icons are (inter)medially condensed signs—what do they actually condense? What ‘ideas’ of technology do they represent or embody? How can the relationship and interrelation between the clown and robot icon be defined—beyond the fact that they are artificially-created beings representing human life transformed into artifice? Exploring these questions by intertwining literary, theatrical and pop cultural history with the history of technology in entertainment, this chapter investigates comic performance and the cultural icon of the comic performer (the clown) as sites through which engineering and technology are represented in Joker-related comic book stories, animated films and (historical) clown robot performances from the popular stage.