Due to the specific history of the black community in the US, in the twentieth century lively writing and storytelling, along with a subjectivity ranging from first-person perspectives to general advocacy, remained commonplace in the conventional black press even as such elements were lost in the mainstream press’s quest for objectivity. The kind of contrast set up between literary and conventional journalism that has been used to help delineate the twentieth-century tradition of literary journalism in the US, which has served as a basis for theorizing about it, does not wholly translate to an African American tradition. Those differences, combined with the double audience the black press has had from its beginnings, indicate that when bringing theory to bear on African American literary journalism, scholars must attend to what Henry Louis Gates Jr. has called the “black difference.” This chapter uses Gates’s theory of “Signifyin(g)” to highlight the black difference in literary journalism by Ted Poston and Charlayne Hunter-Gault.