Ever since its emergence in the late nineteenth century, clandestine political violence against civilian targets has been the object of severe condemnation and abhorrence, while simultaneously inspiring fearful fascination and fantasy. Owing, in part, to its close connection to the modern mass media, the phenomenon known today as “sub-state terrorism” has invariably been accompanied by extensive public discourse on the invisible perpetrators in our midst and their horrifying words and deeds. At the same time, it has spawned numerous terrorist plots in literature and film. The present study sets out to explore the multiple overlaps between these literary and cinematic narratives on the one hand and the wider discourse on terrorism on the other hand, arguing that both draw on, and contribute to, a common imaginary. As the example of 9/11 amply illustrates, terrorist acts tend to trigger a proliferation of “what if” scenarios not only in the realm of literature and film, but also in the statements of government officials, security experts, and journalists. In the process, the discursive boundary between the factual and the non-factual can become difficult to discern, as public discourse both feeds on, and feeds back into, fiction – and vice versa.