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In this chapter, the author returns to whiteface minstrelsy, the more improvisational, free-form mode of whiting up. He places black stand-up comics such as Jackie “Moms” Mabley, Dick Gregory, Richard Pryor, and Dave Chappelle in conversation with black performance artists/actors like Whoopi Goldberg, Anna Deavere Smith, and Sarah Jones to explore the perception and performance of cultural difference. Despite the low-brow connotations of stand-up and the highbrow patina of performance art, there is a shared emphasis on theatricality and self-reflexivity circulating among these solo artists. The fictional characters improvised by Pryor were just as compelling as the studied, mimicry-based re-creations of Smith and Jones. In the 1970s, as Pryor perfected his comedic voice, critics defined his work as “a new type of realistic theater” or “theater of the routine” because Pryor staged ordinary white and black folks in everyday situations. Although Pryor and Smith never shared the same artistic process or venues, they were both committed to fostering dialogues between multiracial publics in fully integrated spaces.

This chapter examines the work of Richard Pryor and his comic successors, who build on his work while taking it in dynamic and unprecedented directions. In particular, this chapter focuses its attention on comedy albums that combine the live stand-up of the comics with recorded bits that reinforce critiques in other forms. So, Pryor’s Bicentennial Nigger uses skits to help reject the romanticized narrative of the United States at the bicentennial. One of the most immediate successors to Pryor was Whoopi Goldberg, whose Direct from Broadway pulls from the template that Moms Mabley constructed by directly confronting the oppression that sits at the intersection of race and gender. However, Goldberg expands on Pryor’s work not through the inclusion of a female voice but by transforming the exploration of black life into a female-centric critique of white, Western, supremacist, patriarchal hegemony. This chapter argues that Chris Rock most effectively realizes Pryor’s legacy of comic rage. Rock’s work, from Bring the Pain (1996) to Never Scared (2004), engages directly with the historical moment of post–civil rights America and is most clearly represented in Rock’s infusion of hip-hop into the structure and style of mainstream stand-up comedy.

As each art form turned confessional, the first artists to attempt it had unusual amounts of social privilege—e.g., among poets, Robert Lowell, a Boston Brahmin. That, perhaps, is why confessional artists have tended to be white, at least in early, pivotal moments in each art form. And yet, over and over, these white, confessional artists have adopted the voices of ethnic and racial others, credentialing their angst through appropriation. Not only is confessionalism unbearably white as a movement, but confessional artists tend to find their own whiteness unbearable. Nonwhite confessional artists, though, do something similar—e.g., in comedy, Richard Pryor—blending personal expression with persona performance, fostering identifications across identitarian boundaries.

This chapter examines fictional depictions of African American presidents as a popular trope in U.S. film, television, and literature, as producing a discourse of “black presidentialism” that implicitly embeds a logic of passing that comes into relief in sketch-comedy performances by Richard Pryor and David Chappelle. This chapter argues that Chappelle’s “counterburlesque” as “Black President Bush,” which rearticulates George W. Bush’s Iraq War policy and its justifications rearticulates in terms of black hypermasculinity and street vernacularities, exposes how popular culture’s discourse of black presidentialism, in its post–Civil Rights era instantiations, invokes what the traditional passing narrative understands as the disconnect between its protagonist’s appearance and presumed essence of his or her identity, with acute attention to the role gender plays in racial semblance. In the case of the black president trope, that dualism is recoded as the tension between the abstracted white manhood of the office of the presidency and black masculine racial particularity.

Privileging imagination and creativity, this chapter is composed of vignettes that consider the complex and sometimes paradoxical relationship between crisis, vulnerability, and empowerment. It begins with Toni Morrison’s Beloved as a theoretical framework for seeing what imagining grace looks like and demonstrating how black feminist theory provides important tools for seeing power in vulnerability and emotiveness. President Obama’s appearance on the cover of Ms. and his accompanying feminist declaration, social commentary on Tom Joyner’s radio show, Donald McKayle’s dance performance “Rainbow ‘Round My Shoulder,” Richard Pryor’s comedy, Presidential initiated social policy, and the visual art of Kehinde Wiley all work together to illustrate how the author both employs and negotiates the challenges of synthesizing black feminist and black masculinity studies. Read together, these vignettes lay out the stakes for critical black gender studies, as well as the complicated nature of constructing complex masculine identities in an era dominated by dialogues of crisis. While vulnerability and emotiveness is privileged in this chapter, the chapter also considers how what Mark Anthony Neal references as illegible masculinities—those expressing vulnerability in this case—are not always a progressive performance that fosters self-actualization and resistance to crisis metaphors.