In this study, criss-crossing discourses – written, visual, and aural – are brought together in an effort to shed light on a section of the tawa’if (traditional courtesan) community in contemporary North India. As a kind of companion text to my point-of-view documentaries Guria, Gossip, and Globalization and Chandni’s Choice, I present an overview of the NGO Guria. This organization works to empower tawa’ifs to reclaim their liminality as artists, able to move back and forth between their own profoundly socially marginalized community and mainstream society, a privilege they enjoyed historically but have virtually lost in the present day. I have juxtaposed this with an exegesis of talk, including gossip, about and by these performers and their music. This includes issues of their gossip- and media-driven legacy that have led to their current position, often dangerously vulnerable, in the global marketplace. Finally, I examine the life of a teenage member of a musical matriarchy whose foremothers have been somewhat successful at continuing to traverse the borderlands between various levels of society.