Focusing on the twentieth and twenty-first centuries, this chapter traces some of the aesthetic choices that Black writers have made in order to demonstrate the essay’s capacious formal dimensions for imagining and practicing freedom. Rather than think of freedom as a destination, African American essayists have revised and restructured the form in ways that allow them to document how freedom is practiced continually. In the essays of writers as varied as Anna Julia Cooper, James Baldwin, Audre Lorde, Amiri Baraka, John Edgar Wideman, Ta-Nahesi Coates, and Ross Gay, reflections on joy, justice, life as art, and self-care unfold freely. From defiance to mournfulness, from exuberance to acrimony, this chapter explores the various moods and modes of Black essayistic writing, identifying certain tendencies that belong to the genealogy of Black writing in the United States.