Reeling under the age-old feudal system and strangled by the dominant colonial power, Kerala society was ripe for drastic transformation during the early twentieth century. Social reform movements spearheaded by Sri Narayana Guru, Chattambi Swamikal, and Mahatma Ayyankali began to influence thinking minds and the age-old beliefs and practices were being unsettled by the strong currents of mass movements. The stage was set for a major reform and regeneration in all realms of social life, including literature. The social reform movements opened the doors for the lower caste individuals to participate in public life, while the freedom struggle and rise of socialism and communism, influenced by the Bolshevik Revolution in Russia, fostered a yearning for equality and liberty. Naturally, literary writings of this period emanated from these social and political conflicts revealed revolutionary impulses, and the desire for the creation of a better world. Progressive writing in Kerala, by and large shares this urge for social transformation. Novelists like Thakazhi Sivasankara Pillai, S. K. Pottekkkatt, and P. Kesavadev, playwrights like Thoppil Bhasi and K. Damodaran, and poets like Kumaran Asan, Ulloor S. Parameswara Iyer, Vallathol Narayana Menon, Changampuzha Krishna Pillai, Vyloppilli Sreedhara Menon, Edasseri Govindan Nair, Vayalar Rama Varma, P. Bhaskaran, and O.N. V. Kurup were extremely popular writers who could considerably influence the Malayali psyche. Flushed and shaped in the turbulent period of the National Movement for Freedom and social struggle against caste hierarchy, poets associated with the progressive movement often dealt with issues related to freedom, caste discrimination, the miserable life of the downtrodden people, and the emergence of the working class as a revolutionary force. The paper will trace the history of progressive turn in Malayalam poetry set in the background of the socio-political transformation of Kerala society.