When are Black feminisms funny? One among the many answers is comedian Amanda Seales’ 2019 HBO Comedy Special, I Be Knowin’. Nearly two generations earlier, Audre Lorde (1984:126) wrote, “…But I hear your laughter is full of terror and dis-ease.” What does self-reflexive laughter full of Black joy and liberation sound like? Ms. Seales answers well. Using the platform from her recurring role on the Issa Rae HBO sitcom, Insecure, in her solo special, she moved back into standup comedy, showing the skills of edutainment, and “the next great.” Her performance is a thoughtful consideration of societal subgroups that position foundations of who she is speaking with and why, before an audience made up almost entirely of New York City Black women. She explores developmental compromises (of integrated schooling), conjures historical figures (Harriet Tubman and others), considers the challenges of dating and 21st century Black love, and many other expressions of everyday Black womanhood. In a dialogue with Harriet Tubman, Moms Mabley, and Audre Lorde, this article analyzes and celebrates the funny Black feminisms of Amanda Seales’ meanings and mission; poet, thinker, and standup comedian.