The relationship between art and politics is complex, often fraught, and cannot always be understood using frames that are anchored by conventional art historical/theoretical analyses. This paper is part of research that started as an attempt to answer what appears to be an innocuous, and simple, question – how does one understand Indian women’s artistic production? In time the attempt to grapple with this question expanded the purview of the research, as the question about gender was constantly being disturbed, and ‘rearranged’, by cultural texts produced by artists, whose self identified positionality (queer, lower caste) was anchored differently. Like the work by certain kinds of women artists, the cultural interventions by Dalit and queer artists disturbed stock expectations of both art and politics, as also the ‘task’ of the artist. Given the difficult and complex relationship that art, politics, and theory have with each other, this paper will be an attempt to read both art works, and the critical writing on art as sites of struggle that navigate these terrains, rather than a process of providing a definitive opinion. In the spirit of such an enterprise, which would be in keeping with the work of many artists whose work simultaneously invokes and critiques political categories, this study shall bring art practices into conversation with the social and institutional context of art production, and the complex histories of circulation and spectation.