This chapter traces the histories of teaching artistry and Drama-in-Education as a constellation of practices informed by multiple cultural, historical and philosophical lineages. The ‘in between’ role of the Teaching Artist brings together complementary skills of artists and educators, existing in a liminal space that requires a sense of play, presence and adaptability. While Drama-in-Education is typically conceptualised as a field rooted in British pedagogy, in reality Teaching Artists are influenced by the specific contexts in which they work, including the vital influence of Indigenous ways of knowing, being and doing. This chapter also considers how process drama, co-creation, emotion, story and the intrinsic value of art are relevant to the work of the Teaching Artist.