This chapter aligns artist Robert Smithson with Thomas Pynchon, a novelist whose treatment of ruins mediates his preoccupation with time, as well as his celebrated critique of conventional historiography. Both were considered key figures in the emergence of postmodernism within their respective disciplines, and shared many preoccupations during the 1960s and 1970s, such as entropy and the paradox of representation without resemblance. Moreover, while Smithson is best known for his site-specific projects in visual and plastic media, he was also a prolific writer of narrative and essayistic prose. Pynchon is most readily appreciated for his experimentation with narrative form, he was equally interested in material sites, or what he calls “nonverbal reality”.