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The ‘conversion’ of slave castes was a complex phenomenon and there are a number of theories woven together by various historiographical schools regarding their conversion in Kerala. While social and economic aspects predominate in the study of religious conversion among the lower castes in South India, most ignore the presence of religious desires among slave caste Christians and their ‘inner transformation’ after encountering protestant Christian missionaries. While caste was also present in the church, experiences of suffering and discrimination that Dalits faced in their everyday lives, forced them to transcend their hardships through prayers, songs, stories, etc. These songs were, hence, not mere expressions, but embedded within Dalit resistance and struggle against within hegemonic power relations. Although, a substantial amount has already been written about the social aspects of religious conversion among Dalits in Kerala, a significant number of Dalit Christian songs have not been adequately analyzed. Though Christian songs were largely used to reach out to larger audiences during the colonial period, these also contained certain specific messages and ideas. The songs informing singers and listeners about the abolition of agrestic slavery in Travancore (1855) were important in this context. However, over time, compositions depicting the discrimination of Dalit Christians, and the caste-based contempt they physically faced, also increased, reflecting the hope and anguish of Dalit Christians. In effect, Dalit Christian songs exemplify a variety of ‘linguistic’ modernity for Dalits in Kerala and the Malayalam in these poems and song were perceived as being uncontaminated by the caste. Finally, Christian songs are important for Dalit history and their search for rights and citizenship in a caste ridden society. The present paper offers an analysis of the Dalit songs in Malayalam with a view to construct new knowledge that will push the frontiers of historical scholarship forward.