In life‐course criminology, when gender has been the focus of study, it has predominantly been treated as a variable. Studies that explore the gendered nature of criminal careers through the lived experiences of offenders are rare, even though these studies can make important contributions to our understanding of crime and the life course. Analyzing qualitative data, this article uses life‐history narratives of a small sample of male juvenile delinquents (N = 25), born in 1969–1974, to explore the possible link among masculinities, persistence, and desistance from crime. The findings of the study suggest that processes of persistence and desistance are imbued with age‐specific norms of what it means to “be a man” and successfully do masculinity in different stages of life. Analyzing these gender‐specific practices gives a deepened understanding of processes that underlie the offenders’ lives as they go through stages of continuity and change in crime. The findings of the study further suggest a complex intersection between gendered biographies and gendered structures, with fruitful contributions to life‐course criminology. The implications of these findings are discussed.