The musical project Crossing Roper Bar (CRB) is based on a collaboration between Wägilak songmen from Australia’s Northern Territory and the Australian Art Orchestra (AAO). Individuals drawn into this collaboration bring their distinct voices and histories to performance, while opening themselves to those of others. A new, malleable approach to orchestral performance in Australia is the result of this collaboration, which places improvisation at the centre of conversational musical interaction. This chapter introduces orthodox narrative elements of Wägilak manikay (song) that are creatively renewed and sustained in CRB. It highlights how the collaboration demonstrates the compelling play of musical performance that can generate nuanced, respectful and ongoing interactions between individuals, and between individuals and traditions. Amidst the vibrant, cultural diversity of contemporary Australian society, CRB suggests new possibilities for productive and relevant orchestral music-making.