The history of writing practices in India has been as varied as the socio-cultural histories of the diverse regions of the subcontinent. The political movements have always shaped and, in turn, been molded by the literary and cultural practices of every region. In this article, it is argued that certain strains of the progressive literature movement in Malayalam, while closely engaging with the left political movements of Kerala, maintained a non-instrumental as well as autonomous relationship with political practices of the region as exemplified in the complex poetic narratives discussed here. The poetic imagination and elucidation of the notion of progress, central to the left political discourse, went beyond and at times against the constraints and limits of mass mobilizations and hegemonic cultural presence. Here, select poems of two renowned Malayali poets of the twentieth century are analysed, focusing on the theme of modernity, what it entails in terms of spatial and material changes, perceived as modernization, and how to grasp and recreate it in the affective registers for the readers/subjects (of the transformation). This possibility further gestures towards a fresh approach to conceiving the relationship between political and aesthetic practices, rooted in the vernacular trajectory, yet informed and enriched by the global discourse.