In this paper we compare the educational attainment of adults who had relatively unhealthy parents when they were adolescents to those whose parents were relatively healthy during this time of their lives. We use data from the National Longitudinal Study of Adolescent Health (n = 13,556) to show that U.S. adolescents whose parents described their health as “fair” or “poor” at Wave 1 of the study were more likely to drop out of high school compared to those whose parents reported better levels of health. We do not observe any association between parental health and the likelihood of attending college among those who graduated from high school, however we do show that completing college (among college attendees) is more likely among those whose parents reported better health when they were adolescents. This association persists despite a wide range of statistical controls including socioeconomic status of the household, the physical and mental health status of the respondent, the grade point average of the respondent, the health behaviors of parents, as well as parental time investment. These findings add an important intergenerational component to research on the relationship between socioeconomic status and health.