Focusing on cultural narratives about men's midlife crises, this article explores the more subtle forms that medicalization takes by broadening and re-orientating the concept of successful ageing away from strictly political, medical or/and sociological discussions of health and ageing and towards cultural representations of masculinity, optimization and the handling of a personal crisis. Using two examples; the British comedy Swimming with Men (2018) and the novel Doppler (2014) by Erlend Loe the article discusses the entanglement of masculinity, crisis and ageing and in doing so argues that cultural narratives about men's midlife crises do more than merely comment on already existing understandings of ageing and should in fact be understood as important components in the ongoing medicalization of middle-aged masculinities.