Epidemiological data indicate that men are overrepresented in mortality rates attributed to both natural causes (e.g., ischemic heart disease) and certain deaths caused by external causes (e.g., motor vehicle accidents). Men's health behaviors are consistently linked to their poor health outcomes, and diverse explanations about what underpins men's health behaviors have been presented by commentators and researchers alike. Recently connections between men's behaviors and dominant ideals of masculinity have provided empirical snapshots about the intersections of gender and health and specific illness events. This study uses a retrospective life course method to describe the connections between health behaviors and masculinity across time among three Anglo-Australian men who were born in the 1920s and 1930s and grew up in Victoria, Australia. The findings from this study illustrate how health behaviors intersect with shifting social constructions of masculinity and are mediated by factors including age, history, social class, culture, and illness.