Chapter 4 proceeds to the first published, but chronologically last, installment of the trilogy, Gravity’s Rainbow, and begins with an analysis of the multiple temporalities of that novel, which are discussed in dialogue with the historiographical theories of Reinhart Kosseleck. It then examines Pynchon’s both bleak and desperately funny depiction of how modernity reached its dark apogee in World War II, where humanity’s romantic affair with technology was finally fully consummated. In particular, this theme is traced through a meticulous analysis of the theme of immachination, which runs through all three novels but reaches its natural (or unnatural) culmination in Gravity’s Rainbow. In dialogue with important critical work by Ali Chetwynd as well as Luc Herman and Steven Weisenburger, the chapter concludes by revisiting the pervasive metaphor of the crossroads and the related theme of complicity in order to discuss whether the novel – and the global trilogy in general – is as relentlessly negative as they argue or whether it poses possible alternatives to the status quo.