I examine how midlife men (N= 542) compare their work and family lives with those of their young adult sons, and how these comparisons affect the fathers’ self-evaluations. Analyses are based on quantitative and qualitative data from the Wisconsin Longitudinal Study. Fathers who rate their work lives as more successful than their sons’ have elevated self-esteem only when they also report being very close with their children. Open-ended interviews reveal that men derive pride from financially supporting their families, yet normative and economic constraints of the “good provider” role prevented them from pursuing their own career aspirations and from maintaining close parent-child ties. Intergenerational social comparisons highlight the distinctive work and family constraints felt by the midlife fathers.