The postcolonial writings of Homi Bhabha (1994) provide an outsider's perspective on Western culture. From that perspective, this article examines white, heterosexual masculinity as one “canonical center” of this culture. I see masculinity currently stressed and in transition, both the masculine subjects themselves and the understanding of masculinity. I examine masculinity psychoanalytically as a paradoxical challenge to an individual man as he develops. I look clinically at the struggle of individual men to become “a real man” in the light of social relationships to others who traditionally were unrecognized as fully equal subjects. I also note how the implicit normative masculine in psychoanalytic theory organizes the analyst's clinical perceptions and countertransference, predisposing her to expect the traditional form of the masculine. A newly examined flexible position is encouraged.