This article interrogates the demarcation of modern and postmodern literature within the context of a critical and inter-textual reading of Thomas Pynchon’s The Crying of Lot 49. Approaching Pynchon’s text from what is essentially a formalist perspective, this reading readdresses the question as to whether or not The Crying of Lot 49 breaks through to a mode of fiction beyond modernism itself. Critics such as Brain McHale have forwarded The Crying of Lot 49 as a paradigmatic late modernist work; a work that does not break through to a mode of fiction beyond underlying epistemological presuppositions. Via a comparative reading that draws on the work of Paul Auster, Bret Easton Ellis et al., it is argued herein that McHale’s otherwise scholarly reading is somewhat myopic. In short, it is argued that although Pynchon’s heroine is driven by an epistemological agenda, the text-scape she inhabits is postmodern.