This article investigates inculturation in the twentieth century in relation to the example and practice of the seventeenth-century Jesuit missionary Roberto de Nobili. Monastic and liturgical attempts at inculturation in South India are examined as well as the critique offered by Dalit Theology. There are four sections: (1) Outline and analysis of the practice of de Nobili, and its theological basis in the seventeenth century. (2) Analysis of the parallels between the praxis of de Nobili and various Christian sannyasi in the twentieth century, e.g. Savarirayan Jesudason, Ernest Forrester-Paton, Jack Winslow, Abhishiktananda, Bede Griffiths and Francis Acharya. (3) Evaluation of the practice, and its theological basis, of these sannyasi and other religious leaders in South India. (4) Investigation of the critique of Dalit Theology of these practices, and possible outcomes for future practice e.g. in relation to inter-religious dialogue.