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This article argues Thomas Pynchon’s The Crying of Lot 49 is a postsecular retelling of the book of Job. The novel not only alludes directly to Job, but shares plot, structure, and theme. Both texts explore religious meaning; divining the nature of the transcendent is the primary task of both protagonists. Further, both texts detail an education in uncertainty: as the voice from the whirlwind “answers” neither Oedipa nor Job according to expectations, each comes to understand the innate uncertainty of life and gains the self-knowledge and wisdom to live fully in spite of and according to this ambiguity.

This essay examines how Don DeLillo employs the apophatic tradition as a means of approaching the transcendent while resisting media absorption and extremist cooptation. Apophatic discourse—discourse that points toward that which is beyond language—honors the dynamic nature of truth, making it well suited to a postmodern, pluralistic era. Yet, apophasis is not just a recognition of the limits of language but a way of approaching the Ultimate that results in personal transformation. DeLillo’s invocation of mystery is often noted but rarely connected to spiritual formation. Yet his work is full of pilgrims disaffected by traditional religion who unavailingly seek spiritual fulfillment elsewhere. I demonstrate that DeLillo offers a standard for discriminating among religious mysteries by chronicling the spiritual etiolation of misguided pilgrims. I then identify apophatic discourse in his work, arguing that DeLillo upholds apophasis as a way of engaging mystery that is self-realizing and redemptive.