This article brings together debates about labour market change, work‐based identities, growing concerns about the problem of working‐class, low‐achieving boys and the identification of a contemporary crisis of masculinity. It draws on a longitudinal study of young men in Sheffield and Cambridge — contrasting local labour markets in England — examining the initial workplace experiences of white working‐class male school‐leavers. Two individual cases are explored in depth, looking at initial working pathways in order to assess the attitudes and actions of young school leavers and their responses to the structural changes in the labour market that have transformed their opportunities compared with both their fathers’ generation and their female peers. The implications for theoretical debates about working lives and the trasformation of gender divisions are assessed.