Drawing on critical analysis of film, the horror genre, the Gothic, and Stephen King scholarship, this book considers Andy Muschietti's IT Chapter One (2017) and IT Chapter Two (2019) on multiple levels: as film (both as individual films and through their interconnected narrative), as adaptation, and as a barometer of the horror film's popularity among fans. Key points of consideration include the significance of the fictional town of Derry as a traditionally Gothic "bad place," the role of 1980s nostalgia in these two films, the complex navigation of memory and trauma, gender representation, queer representation, and the return of the repressed. The terrifying figure of Pennywise the clown is central to this analysis, including consideration of performance, costuming, and significance within the larger landscape of the "scary clown" popular culture trope, and through comparison to Tim Curry's iconic performance in Tommy Lee Wallace's 1990 miniseries. This Devil's Advocate contextualizes Muschietti's films within the larger landscape of King's literary and popular culture influence, as well as the debate surrounding "elevated" horror and the "horror boom" of the late 2010s.