Masculinities vary by organizational context, demonstrating that organizational culture shapes the gendering of work even within the same occupation. The author draws on comparative and ethnographic data collected in two retail environments (large and small musical instrument stores) to understand how a common organizational culture is differently gendered by the organization of work. In these music stores, organizational culture is driven by masculinist fantasies of the rock musician lifestyle. As the products and knowledge of the rock musician lifestyle are made popularly accessible and retail work is deskilled, a style of masculinity based on fraternization and competition takes the place of formal knowledge and experience—reaffirming rock musician as a populist, but exclusively male identity. The article concludes with a consideration of how the de-skilling of retail work reproduces gendered interactions that affirm men’s control over work and its products, even as retail work is presumed to be feminizing.