This paper explores psychosocially the intergenerational transmission of aspects of working-class masculinities through the shaming, embarrassment, and bullying of young unemployed men, when faced with taking up service work they describe as “embarrassing” and “feminine.” The context is the closure of a steelworks in a town in the South Wales valleys, in which the men's resistance to service work is mediated by father–son relationships that dictate what counts as proper manly work. In this study, young men, as well as their mothers and (where possible) their fathers, were interviewed. The interviews reveal a community suffering the effects of intergenerational trauma and riven with complex feelings about masculinity and femininity. These feelings are projected onto the young men, who feel bullied and shamed by their families, peers, and others in the community because they are unable to find gender-appropriate work. The implications of these findings for understandings of youth male unemployment are considered.