Vulnerability, as a way to characterize the movement between passivity, shame, and optimism, rests at the center of the Post-Civil Rights Era debates around representations of blackness. My dissertation examines the implications of the more subtle emotions of passivity, shame, and optimism in contemporary satirical narratives in African American literature and visual culture and focuses on the use of these emotions to counter racial stereotypes and expand notions of black masculinity. In “Laughing at My Manhood: Transgressive Black Masculinities in African American Satire,” I chronicle satirists such as Paul Beatty, Percival Everett, Dave Chappelle, and Aaron McGruder and their use of racial caricatures like Uncle Tom, the Black Buck, and Sambo by interrogating how they pair these problematic figures with emotional responses that disregard issues of respectability in order to question the mythos of the “Strong Black Man.” I argue that African American satire, as a transgressive form, creates the possibilities for its practitioners to construct alternative configurations of black masculinities that contest dominant masculine ideals. In my first chapter, I read the trope of the Sambo, as the ideal representation in minstrelsy that demonstrates the facade of racial authenticity. In Dave Chappelle’s The Chappelle Show and Percival Everett’s Erasure the trope of the Sambo functions as a figure of what Lauren Berlant calls “cruel optimism.” In so far as texts like Everett’s and Chappelle’s pixie sketch demonstrate the problems with the anachronistic reproduction of this minstrel figure, they also make explicit the internalization of historical narratives of blackness and the anxiety that they produce for blacks, and specifically black men at the turn of the millennium. In the second chapter, I compare Eldridge Cleaver’s Black Power Manifesto Soul on Ice and Paul Beatty’s The White Boy Shuffle, arguing that Beatty is able to promote a more masochistic representation of black men’s sexuality opposed to the sadism and promotion of the stereotypical black buck figure in Cleaver’s earlier work. Conversely, Beatty’s protagonist in The White Boy Shuffle does not want to assume the position of race leader that he is being thrusted into by others. The protagonist’s ability to embrace masochism serves as a way to rethink the power dynamic in discourses of sexuality without fear of producing a castration narrative. In the third chapter, I examine the trope of the Uncle Tom in contemporary satire, situating him as an agent of resistance through his ability to embrace shame, as I rethink what resistance means in Derrick Bell’s short story “Space Traders” and Trey Ellis’s short film adaptation of Bell’s work. I argue that both Bell’s short story and Ellis’s adaptation create a sense of empathy with the character that relies on the trope of the Uncle Tom and allows the reader and audience to sympathize with his position. The shift from sympathy to shame demonstrates a shift in resistance and privileges silence and interiority over more oral exterior ways of resistance. My final chapter investigates how The Boondocks, a popular editorial comic strip turned animated television show, becomes regressive around conversations and representations of LBTQA communities.