The Urdu term tawa'if has variously been understood as a term for courtesans or prostitutes in north India. Most scholars see the tawa'if either as an unchanging group of hereditary performers or as women engaged in the 'oldest profession' of prostitution. This thesis attempts to rethink these linear and separate histories of performers and prostitutes into a dynamic historical model across the long duree of the 1720s to the 1920s. Using multiple language sources I first show that a diverse group of slave girls, prostitutes and women performers made up the varied group of the tawa'if. To trace the continuities and difference in their lives across changing historical contexts of courtly culture and colonial cities, I use Stephen Greenblatt's theoretical concept of self-fashioning and see these women as agents of their own identity-making. Delving into hierarchies of prostitution and performance, I argue that the most talented and astute amongst the tawa'if became courtesans and wealthy nautch girls through specific acts of self-representation. Reading their acts in conjunction with their historical images in literary and visual representations, this history sees the tawa'if as historical actors in worlds of image-making. As subjects of courtly culture or urban leisure, the image of the tawa'if could signify both, courtly tradition and emerging modernities of city-life. Rethinking a straightforward history of the 'decline' of the 'courtesan tradition' since the late nineteenth century, I show that if some tawa'if were marginalised as prostitutes by colonial and reformist praxis, others became celebrity entertainers. Through their use of new technologies of print, photography and recording, and strategic political acts such as forming local caste associations, the tawa'if in this history will emerge to be acute observers and participants in the milieux of courtly cultures and emergent nation-space.