This study explores intersections between performance, race and masculinity within a variety of expressive cultural contexts during and after the African American Civil Rights Movement. I maintain that the work of James Baldwin is best situated to help us navigate this cross section, as his fiction and cultural criticism focus heavily on the stage in all its incarnations as a space for negotiating the possibilities and limits of expressive culture in combating harmful racial narratives imposed upon black men in America. My thesis begins with a close reading of the performers populating his story collection Going to Meet the Man (1965) before broadening my scope in the following chapters to include analyses of the diametric masculinities in the world of professional boxing and the black roots of the American punk movement. Engaging with theorists like Judith Butler, bell hooks and Paul Gilroy, Underground Men attempts to put these seemingly disparate corners of American life into a dynamic conversation that broadens our understanding through a novel application of critical race, gender and performance theories. Baldwin and his orbiting criticism remain the hub of my investigation throughout, and I use his template of black genius performance outlined in works like Tell Me …