It has been argued by R.W. Connell that gender equality requires the willing co-operation of men and boys. This study of youth masculinity and singing examines the process through which young people are socialised into the norms of the commercial music industry. It is argued that this industry, which is extremely influential on identities and attitudes, remains patriarchal in its power structures. This patriarchy both constrains and shapes the identities of boy performers and perpetuates the construction of females as ‘fodder’ for music that requires little cultural capital for its appreciation. The paper draws on case studies of boy performers aged between 11 and 14, together with survey work in schools of young people who were asked to listen to the commercial CD recordings made by the young performers. It concludes that, from an initial position of innocence, boy singers and their female fans become socialised into a complicit masculinity that unwittingly perpetuates patriarchal hegemony. Connell's aspiration for men and boy's participation in gender equality is rendered an unlikely hope by the power relationships discussed.