The adage, “a good black man is hard to find,” has been a common refrain in black cultural communities for decades. Using this common saying as a departure point, this essay turns to a similar sentiment within scholarship and challenges readers of black men to move toward more transgressive reading practices. Using performative texts, this essay explores how we might develop new reading practices of a “complex black manhood,” moving beyond a good/bad binary. Jamal Joseph’s pastiche visual collection, Tupac Shakur Legacy and Tarrell Alvin McCraney’s play, The Brothers Size teaches us how to read black men’s bodies and practices of masculinity in new ways. This essay explores how both Joseph and McCraney activate a black radical imaginary that does not begin with damage, but tells an uneasy and complex narrative of black manhood through (re)presentations and resistance to the dominant gaze toward black male deviance. The authors of these texts encourage new reading practices—of “what might be” in black manhood—which move us away from canonical prejudices and reorients us toward new, complex (de)scripts for black men.