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The aim of this paper is to explain how the myth of Orpheus and Eurydice can be interpreted as a journey to self-knowledge in relation to a transgender identity. The multifaceted readings that have been done of the myth such as a heteronormative romance between a husband and wife or as the origin myth for the birth of homosexuality in Ancient Greek culture, provide space to take this interpretation in yet another direction. Specifically, as a journey towards self-knowledge for a transgender identity. It is my aim in this paper to explain how this can be done by insisting on its pairing with the story of Pluto and Persephone from the Underworld. For, the two myths have been intertwined at least since Vergil’s Georgics and have continued to influence each other in subsequent renditions of the episode. While both share the elements of tragic love stories between a man and a woman, it is possible to use Persephone’s genealogy to inform a trans reading of the myth, especially if we consider that she is the granddaughter of the goddess Cybele. Cybele’s importance in this reading of Orpheus and Eurydice is abundantly clear when looking at the goddess’s priests, the galli, whose gender, according to historical and literary accounts, did not conform to the binary. Likewise, Cybele does not always present as a woman in mythology. My aim in this paper will be to show the ways in which I see the gender non-conforming practices and ideas surrounding Cybele work as a frame for a trans reading of the Orphean myth. By closely reading, I’ll analyze Ovid’s version of the myth in the Metamorphoses (Books X-XI). Looking at specific passages of the Metamorphoses, I’ll explain what I mean when considering the story as a journey to self-knowledge of a transgender identity. I will argue that Orpheus and Eurydice are two constitutive parts of a single individual whose struggle to know themselves must pass first through self-negation such as in Eurydice’s death, then trauma via Orpheus’ singing of different tragic love stories, and finally acceptance in the reunion with Eurydice in the Underworld. In my trans reading of the Orphean story, I would like to follow Stryker’s claim that that there is an “unstable yet indissoluble relationship between language and materiality, a situation in which language organizes and brings into signification matter that simultaneously eludes definitive representation and demands its own perpetual rearticulation in symbolic terms” (Frankenstein – 252). For, if transness cannot be defined but also needs to be consistently re-codified, then it is in language that one must look for the space to do so. In this regard, both Catullus (Carmen 63) and Lucretius (De Rerum Natura II, 594 – 643), who have worked with the myth of Cybele, will be used to provide further examples of language of transness surrounding these two myths.