The series Adam Ruins Everything (ARE) provides an opportunity to contemplate White, hipster masculinity and its professed progressivism in U.S. culture. As seen in ARE, hipster masculinity claims—in part—to possess an enlightened social politic, challenging sexism, racism, and heterosexism, yet the figuration of the White, cisgender-male hipster we get seemingly adopts feminist positions as means to insulate and expand his own social privilege. Using rhetorical strategies to win debates against cultural hegemony, the hipster of ARE becomes a superior masculinity, a trusted voice to guide and liberate White women and people of color, centering himself as the source of a singular truth. The essay provides the opportunity to consider ongoing tensions and ironies between men/masculinity and feminism.