This study investigates how the high school experiences of a nationally representative cohort of 1980 United States' high school sophomores and seniors are associated with midlife weight. Drawing from theory and previous research led us to expect that family and high school SES, school type, and curricular tracks could be key dimensions of people's high school lives that had salience for midlife weight, possibly in gendered ways. This premise was largely supported in bivariate analyses. In fully adjusted models, family and high school SES were related to women's midlife weight as measured by BMI and having obesity above and beyond a wide range of control variables including academic attainment and high school weight. Among men, high school SES and private school attendance retained significant associations with having obesity in fully adjusted models. Study findings identify important features of individuals' high school lives that are related to later life weight, and they provide evidence that attainment is not the only dimension of people's educational careers that has implications for weight.