This article proposes to look back onto the Black Canadian works produced around the turn of the twenty-first century to establish some of the decolonial practices they promoted, arguing that they remain pivotal in decentering the colonial gaze that to this day is at the root of anti-Black hatred. In the face of continued structural violence and anti-Black racism preeminent across Canada to date, it attempts to unpack the purpose and means deployed in their early texts by two pioneer Black Canadian women writers, Djanet Sears and M. NourbeSe Philip, to decolonize African cultural memory from the diaspora by teaching us to value African legacies outside of Eurocentric standards. Drawing from feminist anthropologist Rita Segato, it contends that these texts perform a “counter-pedagogy of cruelty,” that is, an act of resistance to all those sociocultural practices by which people are taught, trained, and hardened to the ongoing commodification of others.