This chapter traces the emergence of the sonnet in African American literature to the pervasive influence of genteel conventions. These conventions have widely been regarded as conservative or even stultifying, but they provided black poets with various opportunities for self-assertion in the public sphere. The sonnet was a favourite genre among the genteel establishment, and poets pushed the boundaries of black expression by appropriating the form to subvert racial stereotypes, develop a black poetic subjectivity, and participate in the debate over the memory of the Civil War. In tracing these developments, the chapter repositions the outstanding poets of the period, Paul Laurence Dunbar and James Weldon Johnson, alongside their less-known contemporaries, Samuel Beadle, William Stanley Braithwaite, Joseph Seamon Cotter Jr., T. Thomas Fortune, and Henrietta Cordelia Ray.