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While historians have been increasingly attentive to the politics and culture of social movements since the long sixties, they have engaged much less with the significance of anarchism within these activist currents. As part of an emerging field of anarchist studies, this article demonstrates that anarchist projects were critical in shaping postwar political radicalism in Vancouver and its relationship to a global pattern of cultural transformation, capitalist restructuring, and social movement activism. Specifically, the article investigates how and why Vancouver’s anarchist community created strong political, personal, and cultural connections with an emerging punk scene during the 1970s and early 1980s. It demonstrates that these relationships emerged from anarchism’s conflicting relationship with the city’s New Left and countercultural communities in the long sixties, as well as from anarchists’ specific engagement with punk as a tool for revolutionary struggle in the wake of the sixties. Overall, the article argues that anarchists cultivated connections with punk in this context because they saw it as awash with the potential to bridge generations of political dissent; to support emerging activist projects; and to help usher in new expressions of radical culture in the city. In so doing, the article offers new insights into the political, social, and cultural legacies of the long sixties, in Vancouver and beyond.