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This essay aims to examine the figure of the “Asian American detective” in Leonard Chang’s Over the Shoulder. I address in particular the various ways in which Chang attempts to confront the shadow of Charlie Chan, the emasculated and exoticized stereotype of Asian American masculinity. For one, Chang tries to remasculinize his detective-hero Allen Choice by reframing Asian American masculinity within the “hard-boiled” detective genre, wherein the tough guy protagonist embodies all-American normative figure of hegemonic masculinity. However, I contend that simply placing his protagonist in the tradition of hard-boiled detectives proves to be insufficient as Chang tries a different way to recuperate Allen’s manhood: by diluting the significance of race and ethnicity so that Allen may finally move out of Charlie Chan’s shadow of racial stereotyping. Ultimately, I argue that it is critical that we closely investigate what may be at stake for Chang (and his protagonist) in trying (somewhat in vain) to undermine the significance of race within a genre whose bias against nonwhites ultimately reinforces the staying power of the racist discourse in America.