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Translating time- and context-bound subjects cross-culturally requires creative negotiations that often exceed the usual challenges a translator faces. Translating Andy Warhol’s writings, ever so resistant to translation for multiple reasons explored here, presents layers of complications that might make one question if the effort is even worth it. Drawing upon the insights of veteran translator-scholar A.K. Ramanujan and Bhupen Khakkar, India’s first Pop artist, this article speculates on how one may approach a translation of Warhol’s writings into Indian languages other than English and why such an enterprise has yet to be undertaken even if it were to be desirable and possible.