In early modern India, and particularly South India—from roughly the sixteenth century until the eighteenth—a new literary vogue emerged in all major literary traditions (Tamil, Telugu, Kannada, Malayalam, Sanskrit, Persian). With remarkable salience, we find verses built around absurdity of various kinds and modes. Sometimes it is a matter of pushing the existing literary conventions and figures to an impossible extreme. In other cases, we find a fascination with asymmetry, disjunction, skewed causality, and irrealis or counter-factual linguistic forms. Although such experiments with absurdity have precedents in classical kāvya, the evident consistency and intertextual relations among outlandish poems in this period are very striking, as is the fact that the theoreticians of poetics found it necessary to posit a grammar for them (including for poems based on asat, that is, non-existence or sheer impossibility). This essay explores the forms and logical underpinnings that this fashion for the bizarre assumed; we also offer a tentative explanation for the new trend. The prabandha-based poems of absurdity need to be distinguished from the coded texts known in Kannada as beḍagina vacana and in early Hindi as ulaṭbaṃsi, in which an upside-down or inside-out world is created, the goal being to arrest intellection altogether. We also show the distinction between the poetry of the absurd in the early modern texts and the European Dada movement, which aims at unravelling language and enshrines a principle of pure randomality in the choice of words.