The essay focuses on the uses and significance of the trope of passing, as both theme and literary strategy, in African American fiction from the 19th to the 21st century. Passing as a theme pushed the boundaries of arbitrary, but operative, racial dichotomies, while passing as a literary strategy enabled radical experimentation with novelistic conventions. African American writers revised the tragic mulatta and mulatto characters by articulating a black-centered racial imaginary that infused the trope of passing with profound political and literary relevance. Deploying the high visibility of all-but-white characters as a screen to introduce new figures in American literature, they advanced a far from monolithic understanding of blackness that foregrounded its intraracial diversification and intersection with gender and class. African American writers adopted the trope of passing in order to expose the sociopolitical construction of “race,” unsettle prevailing racial epistemologies of blackness, popularize a more complex racial imaginary, and teach self-consciously critical modes of reading literature and, by extension, reality. Through a diachronic approach, the essay shows how the trope of passing was repurposed in different literary-historical periods and how it retains its relevance as a malleable literary strategy of cultural and political intervention.