Mad Men’s seventh season introduces a conspicuous and ominous element of mise en scène: the mammoth IBM 360 computer. It is an obvious metaphor for change, but a deeper analysis reveals more about who and what constitutes an ‘employee’ in an evolving capitalist landscape. Much like Chaplin’s Modern Times (1936) reflected anxieties about the welfare of labourers of the early twentieth century, Mad Men offers a similar kind of exploration of work in America after the midpoint of the century. This chapter offers an intermedial perspective of how these two texts from different eras are strongly in dialogue with one another. I argue both interrogate themes that offer a warning of dehumanization through techno-displacement and illuminate fears over technology as panacea.