This chapter highlights the political function of comedy as a device that interrupts dominant politics of marginalization, shifting attention beyond the formal elements of source and target texts, and beyond the reductive question of whether humour can be carried across languages, to the polemic, social and political functions of comedy. Drawing on contemporary Tamil Dalit literature, in particular Bama’s Karukku (1992) and Caṅkati (1994) and the anthology Dalit Ilakkiyam: Enatu Anupavam (2004), it demonstrates how black humour, scatological and non-standard Tamil are employed to disrupt entrenched hierarchies of Tamil literary taste and challenge the social and political oppression of Tamil Dalits. English translations of these works of fiction painstakingly convey the grotesque, antagonistic nature of this writing in order to offend their target audiences in a different way. Most Anglophone, especially Indian, readers belong to the ‘perpetrator’ sections of society and are therefore in the extraordinary position of empathizing with Dalit characters even while becoming aware that they themselves are targets of Dalit satire. The chapter argues for widening the study of translating comedy, defined not as humour but as a powerful and satirical political tool of resistance and radical questioning for writers, translators and their respective audiences.