This essay reflects on how social unrest and violence are responded to in the mainstream visual arts of postcolonial Jamaica. The focus is on two particular moments of crisis: the social unrest and political violence during the Michael Manley administration in the 1970s and the current escalation in violent crime. Both moments have also coincided with intense cultural activity, in which the lived experience of these crises commands centre stage. This essay explores how this has resulted in visual art works that record, critique or seek to transcend the crisis at hand and how these, along with the popular visual culture and the news media, forge the visual imaginaries of these moments and the visual memories of the future. The essay also reflects on the role of art in times of social crisis and the ethical questions that surround the artistic representation of violence and trauma, especially in the market-driven context of contemporary Jamaican art.