This article assesses what the concepts of community and viability might mean within Canadian theatre over two generations of practitioners. The analysis considers two recorded public interview panels, consisting of four theatre professionals and a moderator, hosted by the University of Toronto. The first of these meetings dates from 1973, and the second was convened as a response to it, in 2015. Each of these panels was held for participants to reflect on the challenges faced by Canadians working in Toronto theatre, and included artistic directors, playwrights, and performers. In both panels, across decades, several overlapping areas of concern were identified. Ideas responding to ideas of community and viability were prominent in each discussion. Concepts such as nationalism and identity were contested. Can theatre workers authentically speak to, and even for, a community of people through the practice of their craft? Is a progressive theatre viable, as both a culture and a business, within an English Canadian context?