This article explores the cultural work of white masculinity in barbershop quartet singing in two historical contexts: the barbershop revival of the 1920s and 1930s and barbershop's struggle for survival in twenty-first century Philadelphia. It first details how revivalists attempted to re-create Victorian white masculinity by codifying and promoting a barbershop musical style and repertory that fostered closeness between men. By performing their musical style in public, masculine spaces, and admitting only white men to their gatherings, the organizers of the Barbershop Harmony Society opposed a number of contemporary social changes in the United States, including shifting gender roles, a rise in immigration, the economic instability of the Great Depression, and New Deal liberalism. The article then documents how and why barbershoppers in Philadelphia at the turn of the twenty-first century still perform this “close,” neo-Victorian mode of white masculinity. In this new context, barbershop whiteness enabled a group of white men to claim belonging in their racially divided city despite years of migration and displacement caused by deindustrialization and urban decay. In both historical moments, barbershoppers used whiteness to challenge social and economic change and to assert the continued relevance of their musical style.