The founding of the All-India Progressive Writers Association in 1936 in Lucknow inaugurated the progressive socialist ideological thrust in the regional literature of India. In this essay, an attempt has been made to recount the history of progressivism (murpokkuvatam) in Tamil literature by focusing on the initiatives and literary output of a few mid-twentieth-century literary figures and cultural activists in Tamilnadu. While attentive to the international and national situation, the rise of progressivism in Tamil literature is examined here in the context of Tamil modernity and the specific regional cultural and political developments in Tamil country. In particular, the historical regional context in which the progressive literature emerged and the challenges it confronted were presented critically from the lives of Tamil literary and cultural activists from 1940 to 1970. Although the organizational form and expression for progressive literature in Tamil took shape only in the early 1960s, there were efforts made by individual writers and cultural activists in the form of launching literary magazines and introducing new trends in literary compositions and literary criticism from the 1940s. Examining these developments in the regional context necessitates situating Tamil progressivism in relation to the challenges of caste, literature, and regional identity central to Tamil modernity.