This paper aims to analyze the shift in casteism in Kerala society through selected prominent literary works of the times. While N. Kumaranasan dealt with the social marginalization practiced against "untouchables" in Chandalabhikshuki, O. Chandu Menon in Indulekha tries to represent the internal casteist conflict among the "upper castes". The Renaissance movement led by SreeNarayana Guru, Ayyankali and Mannathu Padmanabhan heralded a new era in Kerala's social scenario by toppling down, to a great extent, the segregation prevalent in the society. Besides Renaissance movement, a further shift occurred in the Malayali casteist mindset with the progressive Communist movements as well. Thakazhi's novels like Randidangazhi and Thottiyude Makan succeeds in addressing the problems of lower castes while emphasizing the role of class struggle within casteism. Furthur, P.Kesava Dev pointed out in his Ayalkar that with the emergence of Communist movement, there occurred a significant amelioration of Ezhava community. The deterioration of theocratic feudalism and matrilineal system, also contributed considerably to build a more inclusive Keralite society. Casteism, during those times, has received much condemnation but paradoxically it had a large number of adherents in practice. Towards the end of twentieth century, "the caste", which was publicly condemned till then, began reasserting itself in the minds of Malayalis. O.V. Vijayan through his work Thalamurakal throws light on the implicit casteism and Malayali's propensity to attain Brahmanism to be on par with the "upper castes". Truly, no one dare to speak out "caste" in today's Kerala but the hard fact that caste is deeply ingrained in the mental fabric of Keralites cannot be left unnoticed. Manushyanu Oru Aamukham, the Sahitya Akademi Award winning novel by Subhash Chandran, fundamentally presumes every educated Keralite who swears against casteism, as being unknowingly bound by it.