This dissertation examines the possibilities and anxieties that attend a notion haunting Western thought since at least Kant--that reality itself is a revisable construct, a kind of collective game with social and physical rules that simultaneously delimit and solicit radical interactivity. Investigating experiments in the gamification of reality avant la lettre, I consider select authors and game designers from the mid nineteenth century to the present who not only depict otherworldly fictions but also insist that such endeavors have the potential to make the world otherwise. This project draws on recent scholarship in game studies, cognitive science, social constructivism, Black studies, and current headlines regarding climate denialism, the "big lie," and the metaverse, to argue that increasing investments in reality's "hackability" over the past two centuries hold forth the prospect of both greater freedom and greater constriction, expanded capacity and enlarging forms of control. Viewed ever more as a game, reality has never been more, or less, in play--for better and for worse. Chapter One contends that Edgar Allan Poe's Eureka (1848) is an earnest cosmological attempt to chart a dynamic, coextensive relationship between individual and environment by using a form of knowledge he calls "intuition." Poe's intuitive detective, Auguste Dupin, in "The Purloined Letter" (1844) and "The Murders on the Rue Morgue" (1841) defines intuition through a game called "Even and Odds," which I argue showcases how game systems can be used to navigate reality's newfound flexibility. Whereas Poe's playful paradigm highlights a positive, crime-solving outcome, Chapter Two reads Lovecraft's mythos as a system written with a racist source code that contemporary video game adaptations, such as "Call of Cthulhu" (2018) and "Control" (2019), fail to transcend. However, I analyze Victor LaValle's "The Ballad of Black Tom" (2016) as successfully recodifying racism as the true monster of Lovecraft's worldview, embodying transgressive and transcendent "game" play despite being a generically conventional novel. Arguing for an intensification of personal and social immersion in evolving media technologies over time, Chapter Three positions Virtual Reality (VR) as a space capable of either reinscribing societal limitations or fashioning responsible, just realities. I build on Stewart Brand's experimental New Games movement in the 1970s and Karl Groos' theory of social evolution through play to argue that radical play in virtual spaces is essential to combat the condensation of the self into marketable data. Finally, inspired by LaValle's precedent, the Coda chronicles my development of a theoretical game design that reworks Lovecraft's cosmos into an experiment in collaborative, anti-racist world-building. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]