The labyrinth is both a physical and a metaphorical space and both dimensions have had a role to play in various literary cultures throughout the ages. This is especially the case of postmodern works of fiction, where the idea of circuitous routes, dead ends, and false starts brings to mind the trope of the labyrinth. A post-postmodernist writer like David Foster Wallace, however, found that the desire for an exit from the maze pointed to a spiritual dimension that he deemed to be missing from American postmodernism in general. This chapter attempts to trace a hitherto underexplored link between Laurence Sterne’s Tristram Shandy (1759–1767), an ur-text of postmodernist fiction, and Wallace’s Infinite Jest (1996), and it does so by judging both works based on their perception of the labyrinth. If a writer like Sterne reveled in getting lost in his own literary maze, Wallace’s version of secular faith sought a “vertical” escape from what we may describe as the postmodern hall of mirrors.