This paper focuses on two cohorts of Norwegian young men whose behaviour in childhood and adolescence caused serious concern to their parents, teachers, social workers and, in some cases, the police, Despite having been identified as ‘at risk’, they made transitions to positive adult masculine identities in two different historical contexts; the 1980s and 2000s. The paper analyses the difference that historical context makes to these young men’s lives, their gendered identity work and their perspectives on their past, present and future. In particular, it identifies the ways in which supportive intergenerational relationships and significant others serve to produce positive turning points and, over time, help the young men to develop resilience and potentially happy and successful futures.