This article argues that hair modification by Black males in Latin America is both a resistance and reinscription of white cultural hegemony. Using the films Pelo malo (2013), by Mariana Rondón, and La playa D.C. (2012), by Juan Andrés Arango García, I demonstrate how socially constructed notions of race and masculinity imposed on Black males are both reproduced and resisted as natural survival mechanisms. While Pelo malo’s Junior is ultimately defeated by social expectations that subjugate Blackness, La playa D.C.’s Tomás triumphs in socially oppressive systems and becomes a barber through his hair. By evaluating the two films together, this article shows how hair for Black males can be both an object of oppression and a source of pride. In this examination, we see how Black males straddle an in-between existential reality that pushes against the one-dimensional subjectivity often imposed by hegemonic identity rhetoric. In the end, this analysis exposes how Black men use hair to dismantle racially imposed subjugations and masculinist definitions in order to decolonize toxic constructs of Blackness and manhood.