This essay spotlights black pessimism within the “Age of Obama.” Looking to the Black Lives Matter movement and several artistic responses inspired by BLM, it identifies the rise of “black pessimism” within the Age of Obama. This essay engages the frequency of black death—such as the killings of Trayvon Martin and Philando Castile among others—against a backdrop of proclaimed hope and optimism: “Keep Hope Alive” and “Yes We Can.” It points to theater as an artistic form that has not only engaged and promoted social activism, but also reflected this widespread sense of pessimism.