How does psychoanalysis animate racial passing and how does racial passing inspire psychoanalysis? Despite long-held beliefs that the two have nothing in common, Donavan L. Ramon poses that psychoanalysis is relevant for understanding the reasons behind jumping the color line. Beginning with the premise that Sigmund Freud created psychoanalysis to contend with his own anxieties about race, Ramon explores canonical and non-canonical passing narratives using psychoanalytic perspectives. He closely reads narratives by Charles Chesnutt, James Weldon Johnson, Nella Larsen, Alice Dunbar-Nelson, Jessie Fauset, Anita Reynolds, Danzy Senna, Vera Caspary, Anatole Broyard, and Philip Roth to advance several provocative claims about the intersections of passing and psychoanalysis. Chief among them are the youthful trauma and psychological consequences of racial passing. For instance, while the death drive motivates fictional racial passers to hasten their own deaths, those who pass in real life often seek their own immortality through print despite hiding their Blackness. Throughout this analysis, Ramon underscores the nuances of racial passing in school as the place of trauma for Black subjects. Ramon's work is deeply interdisciplinary, threading psychoanalysis and other theoretical perspectives throughout persuasive close readings of twentieth and twenty-first century racial passing narratives. The monograph concludes with a meditation on today's ineffective language of race, which hinders racial progress. Scholars of race, African American Literature, American Literature, and psychoanalysis will find Ramon's book compelling.