This chapter explores Black masculinity and celebrity at the turn of the century through the lives of American statesman Frederick Douglass, educator Booker T. Washington, scholar/activist W. E. B. DuBois, fiction writer Charles W. Chesnutt, and boxer Jack Johnson, the first African American world heavyweight champion. Johnson’s athletic accomplishments and diverse cultural interests, along with his uncompromisingly bold personality, set a new tone for Black masculinity in the first decade of the twentieth century. His celebrity status, mediated by his status as a Black man, provided him a public platform unprecedented for an African American man. On that platform, he embraced his Black working-class heritage, critiqued the dubious history and practice of colonialism, and unapologetically revealed his preference for socializing with white women. Johnson presented, in both his actions and his physical dominance of white men in the ring, the major issues, aspirations, and concerns in the lives and work of this quartet of Black men.