This article proposes a dynamic model of the intersections between gender, health, and the life course incorporating processes of strategic selection--of roles, relationships, and behavior. Men and women make decisions within a tangled web of multilayered, often contradictory, and frequently outdated institutional contexts of opportunity and constraint. Both their decisions and the institutions shaping them reflect prior as well as ongoing socialization and allocation mechanisms. These institutionalized scripts and regimes tend to reproduce gendered biographical paths around two central life foci: paid work (or careers) and unpaid family work (or careers). The gendered nature of occupational and family-care paths, in turn, produces patterned disparities in a constellation of health-related resources, relationships, and risks, as well as feelings of mastery and control. We call for research charting alternative constellations of these gendered health careers, their antecedents, temporal patterning, and consequences.