Caste is gaining unprecedented importance as the proxy for social inequality in India. In this context, how is caste structuring the social lives of urban residents, and how are urban interactions mediated by participation in cultural activities? This project studies the processes by which caste group boundaries are drawn, contested, and remade in urban India through the cultural domain. Taking the case of Chennai, I study two musical art worlds known as Carnatic music and gaana music, each associated with upper caste Brahmin and untouchable Dalit groups respectively. Music has become the terrain on which caste group boundaries are articulated in Chennai, resulting in contestations over cultural, urban, and social spaces. I employ an ethnographic approach combined with in-depth interviews to excavate the daily lives of people circulating in these art worlds, and observe how caste is performed, spoken about, and enacted in covert and overt ways. A rich ethnographic account of caste articulated through culture will also illuminate the ways in which movement and occupation of spaces come to be negotiated on the basis of caste identity and grouping. The importance of my research is in filling the lacuna on the lived experience of caste in modern, urban India. I build upon a range of sociological, anthropological, and historical studies to develop a theory of caste in the context of India's rapid urbanization and staggering inequality.