The emergence and history of South Africa’s cultural worker, at least since the 1970s, occupies an anxious and ambiguous relation to political power. These relations, in my view, have taken on consensual and dissenting forms. In their constitution, cultural workers have acknowledged their roles as intermediary and critic. The South African cultural worker also echoes an international political subject position, where artists and cultural producers forge alliances with, or belonging in, social and trade union movements. Lee Walters begins this discussion with two moments, separated by fifty years. The first introduces “Abahlali ba se NAC”, a political arts occupy phenomenon, currently unfolding at South Africa’s National Arts Council in Johannesburg. The second moment, comprising two movements involving the internationally acclaimed artist Mariam Makeba, recorded at the United Nations and aired on YLE-Finland in the 1960s, brings attention to the anti-apartheid struggle. Using these provocations, Walters considers the relationship between resistance politics, the arts and cultural work. Drawing on documented narratives from cultural workers as well as on conversations, interviews and reports that came to light during this research, Walters interprets assemblages of social dynamics and ambiguous features that consistently trouble this identification: cultural worker.