This article reflects on portrayals of businessmen in TV and film and considers the ways in which this has significance within society, particularly in relation to competing understandings of masculinity. To show this more concretely we provide a nuanced exploration of exemplars of dominant representations within these fictional accounts ranging from Charles Foster Kane (Citizen Kane [1941]) and Daniel Plainview (There Will be Blood [2007] to Don Draper (Mad Men [2002]) and Logan Roy (Succession [2018]. In our analysis we pay particular attention to how businessmen in fiction portray evolving and contrasting understandings of hegemonic (and counter hegemonic) masculinity through their on-screen dialogue, actions, and behaviour. To achieve this, we draw on the metaphor of ventriloquism to show how - via on-screen depictions of businessmen – masculinities both ‘speak’ to audiences (e.g., affecting their sense of self) and are reciprocally made to ‘speak’ by audiences (e.g., masculinities become reinforced, subverted, or resisted) through their talk and general conduct. The article is offered with the intent of enriching organization studies as a discipline, which rarely explores the wider cultural influences on what we consider to be “the businessman” and how they might see and understand themselves.