The concepts of utopia (a good place) and dystopia (a bad place) might be arrived at and developed by one’s contact with the (constructed) reality and comprehension, yet frustration and discontent with it, and one’s pessimism and optimism over a better present and future contingent upon the place and time in which one exists. The former has a long history, whereas the latter is a work in progress. That is, one cannot simply distinguish between the two by asking whether the latter is primarily precautionary and reactive, cautioning us what not to do, whilst the former is proactive, pointing us towards the right direction. Both the former and latter may have similar motives, namely, to demonstrate the dark characteristics of one society by comparing it with another, fictitious culture. Someone’s utopia might alternate dystopia, or many traditional utopias from the past include aspects that modern readers would identify as dystopian. On the other hand, one could argue that dystopia serves as the worst-case scenario, presenting a degraded, collapsing, and/or collapsed society, be it socio-culturally, economically, or technologically, worse than another, yet still hopeful for a drastic change for the better. Utopia could be received as the best-case scenario for people in a society considering its socio-political demise. Shortly, both utopian and dystopian scenarios would fit into an extended framework of contemplations on a catastrophe that would either signal a tremendous shift for the better or result in an apocalyptic nightmare. Drawing on the standpoints of Giles Deleuze and Jean Baudrillard and tracing Don DeLillo’s fiction, this paper seeks to explore the notion of dystopia, the future assumptions that dystopian fiction puts forward, and the challenges and issues it highlights, such as digital surveillance, technological control, the disappearance of individualism, uncertainty, and dread.