Beginning with a reading of a short manuscript fragment, A Rabelaisian Rhapsody (1898–1900), this chapter shows that this short dramatic dialogue affords us a unique and overlooked insight into the structures and key concerns of Synge’s entire dramatic oeuvre. In doing so, the chapter excavates many new influences on Synge’s work through a close reading of new source materials by Jacob Boehme, Spinoza, Blavatsky, Nietzsche, Hegel, Rabelais, Paracelsus, and a number of esoteric figures, reinforcing the continued importance of mysticism to his dramatic development. In The Well of the Saints (1905), we find the final synthesis of the dialectical structure of ‘A Rabelaisian Rhapsody’, and the preparation for Synge’s overt sociological statements regarding modernization in Ireland in his articles ‘From the Congested Districts’, published later the same year. Synge established a spiritual basis for his aesthetic, countering asceticism with pantheism, restriction with Rabelaisian excess. The various iterations of this conflict can be traced over numerous dialogues, scenarios, and plays in his oeuvre, and this dialectical structure became subsumed into a larger literary vision of nonconformity and multidirectional irony. In turn, Synge’s spiritual and aesthetic opposition to ascetic or conforming figures began to influence his understanding of political and social change in contemporary Ireland. Finally, this chapter demonstrates that by reading The Well of the Saints as a play based in Ossianic dialogues, nineteenth-century Celticist readings of racial difference, and conflicting modes of production, we can begin to understand Synge’s drama as one urging consciously towards protest and designed political impact.