A major objective of current life course research is to specify the processes linking early childhood conditions to subsequent life course statuses that span educational, occupational, familial, and health domains across the life span. This study confronts at least two persistent challenges to the rigorous specification of the relationships among these variables. The first is that the point-in-time measurement of education as "years of schooling" masks considerable heterogeneity in the timing and curricular tracks of schooling and obscures our understanding of how and when education matters for life-course inequality. The second challenge involves interdependencies between aspects of life-course inequality, including educational achievement and health. The intertwining of these variables across the life course, and their usual conceptualization and measurement, limit the interpretation of their relationship and its generalizability across studies. We use data from three waves of the National Survey of Families and Households between 1987-1988-2002 to explore trajectories of self-reported health, applying latent class cluster analysis (finite mixture models) to deal directly with these measurement and specification issues. Generally, we find mediating effects of education in mid-to late-life health demonstrating the pivotal role of education in life course processes. Women's childhood backgrounds are more heterogeneous and temporally complex educational careers affect their self-assessed health more than men's. Late degrees are linked to poor health trajectories among women, but not men. Also, marital history, number of births and health behaviors are associated in expected ways with women's and men's health trajectories at midlife.