Teaching Artists often work in language learning contexts, where they face a range of demands on their skills in both drama and language, and must balance artistic and aesthetic concerns with pedagogical demands. This chapter includes a personal reflection on the author’s own experiences as a Teaching Artist working in various language learning settings, before introducing a real-life research context involving a group of Community (or Heritage) Language teachers from culturally and linguistically diverse backgrounds participating in a series of process drama workshops. Community Language schools form a unique and important role in the landscape of language education in Australia and internationally. This chapter suggests that there are many resonances between Teaching Artists and Community Language teachers, including their position on the peripheries of mainstream education and their readiness to adopt creative and translanguaging approaches where students can bring their whole selves into the classroom.