Despite the recent interest in multiple "masculinities," previous research has either ignored older men or implicitly treated them as without gender. In order to fill this gap in the literature, we conducted semi-structured interviews with men born in the early 1930s living in the west of Scotland. Disruptions to individual biographies (due to the illness or death of a spouse or loss of their job through redundancy) forced men to reevaluate previously taken-for-granted attitudes to gender roles. Social class trajectories were important in shaping men's attitudes to paid work and gender roles; for example, men who were upwardly mobile were most egalitarian about the gendered division of labor in the household. More privileged men also constructed masculinity differently from less privileged men. Our findings suggest that more attention should be paid to the variety of ways in which older men "do" gender.