This article explores the gender complexities of men caught between social power and powerlessness. Specifically, I consider the cases of Jewish men and gay men in the late modern West, two demographics with deep historic ties to both abjection and privilege. Such "in-between-ness” steers many, especially those who are white, cisgender, and/or otherwise privileged, toward what I term liminal complicity, a normative adaptation whereby men embrace manly ideals while disavowing femininity in themselves and others. I synthesize cultural, interactionist, and psychoanalytic literatures on stigma, boundaries, and gender practice to articulate liminal complicity as both an emotional retreat from stigmatization and a rational means of accruing status and redrawing social boundaries. I conduct a comparative-historical analysis of gendered discourses and practices at different historical junctures to show how analogous processes of (1) normative identification, (2) self-transformation, and (3) distinction from and (4) aggression toward feminized others enable historically subordinated men to elevate themselves without disrupting broader systems of domination.