This chapter revisits W. E. B. Du Bois’s The Souls of Black Folk in the effort to draw out a relevant tension in the text. On the one hand, Du Bois seems to assimilate black strivings into a progressive, teleological narrative that finds its culmination in the civic nation and the ideals of freedom and democracy. On this reading, Du Bois follows a rather optimistic reading of Hegel’s related notions of reconciliation and mutual recognition. On the other hand, Du Bois suggests that the sorrow songs, one of the gifts of black people, indicates and expresses a legacy of agony, struggle, creativity, and hope that challenges reductive interpretations of America’s racial history. By underscoring and unpacking the sorrow songs, Du Bois accents what Hegel, and more famously Adorno, calls the labor of the negative, which interrupts and refuses strivings toward unity and agreement. As Du Bois shows piety toward slave songs and spirituals, this musical legacy also becomes an occasion to reflect on the relationship between black piety, remembrance, and loss. To elaborate on the critical work that melancholy can do with respect to continuous, linear accounts of history, this chapter also uses ideas from Walter Benjamin’s classic essay “On the Concept of History.”