Abstract: The narrative of interracial male bonding---in which white and black men forge friendship outside history and institutions---has long been faulted for expressing a white male desire for a utopian racial harmony that denies white complicity in historical racism and marginalizes black subjectivity. This dissertation challenges the adequacy of that appraisal by demonstrating how selected antiracist, twentieth-century American male writers and filmmakers on both sides of the color line---Richard Wright, William Faulkner, Lloyd Brown, Alfred Hassler, Donald Goines, Norman Jewison, and Bill Duke---deploy the representation of interracial male comity as a means of consciously and critically revealing, rather than merely concealing, the structural foundations of racial inequality in America from late Jim Crow through the post-Civil Rights era. Eschewing the Fiedlerian open spaces and Anglo-centric approach that have defined affective male relations in American literature and film, these artists position black-white dyads within the confines of the institution arguably most instrumental in the maintenance of racial hierarchies in the twentieth-century United States---the criminal justice system---and use the resulting 'institutionalized' bonds as vessels through which to expose and resist patterns of racial subordination. Each chapter centers around texts that configure black-white male relationships as direct products of---and political responses to---the site-specific exigencies of the justice system's three main nodes: the courts, the prisons, and the police. In novels by Wright and Faulkner, for example, the white lawyer-black client dyad becomes a heuristic for dramatizing how black male 'criminals' struggle for adequate hearings in legal arenas that ignore black subjectivity. In the anti-'buddy-cop' films of Jewison and Duke, the black-white police duo provides an unexpected venue for examining the crisis of racial authenticity faced by African-American policemen who work for a law-enforcement institution with a historically vexed relationship to black communities. Each chapter shows how the institutionally 'bound' male bond functions as, among other things, a counterintuitive means of clearing narrative space for the expression of black male subjectivity and an ethical tool for exposing the way in which white-controlled legal authority often predicates its power on the false expectation of black male criminality.