She became a professional singer/songwriter, performing at various venues around the world. Two producers from Canada's public film producer and distributor, the National Film Bureau, heard Obomsawin's Abenaki singing in 1967 on television and invited her to consult on an aboriginal story film. She then began to produce her own material, creating more than 30 documentaries.
Interestingly, it is the armed conflict between aboriginal Canadians and the municipal, provincial and federal Canadian governments that is the subject of Obomsowin's most well-known documentary. Her four-film series on the Oka Crisis of 1990 documents what the Toronto Globe and Mail newspaper referred to as "the ... most significant event to take place on Canadian soil since the Second World War."