This dissertation examines the lives and the worlds generated by three figures namely: Ramana Maharshi (1879-1950), Jiddu Krishnamurti (1895-1986) and Osho (1931-1990). Drawing on religion, anthropology and media studies scholarship, this dissertation takes a unique approach in understanding these figures. Moving away from the established approaches within guru studies, I propose a new mode of analysis: a theory of the figure. A theory of the figure is a broad mode of analysis that enables the study of different relationalities, discourses, media, practices and circulation of ideas. This mode of analysis can be applied to varied contexts to unpack gurus and their worlds. Secondly, it focuses on the methods and ideas that led to the formation of certain practices of self-transformation as given by each of these figures. By taking these three figures as examples, it aims to understand discourses of self-transformation in modern India. Moreover, it focuses on the role of mediation in constructing such discourses. These discourses and their mediations are generated in within a context of transnational encounter between seekers and figures that destabilizes categories of “east” and “west.” The dissertation demonstrates that, by studying the processes by which the figures come into being, new insights on community formation, pedagogy, and circulation of ideas can be gained. In particular by focusing on the role of media in these processes, we can understand how transformative experiences are structured by them and vice versa. The dissertation argues that the figure of Ramana is produced within the practices of photography, the act of writing, and the method of self-enquiry (who am I?). The figure of Krishnamurti is produced through dialogic modes of pedagogy and a sonic imagination. Finally, the figure of Osho emerges from the multiple and dispersed archives, the technologies of meditation and a discourse on ‘devices’.