The current impact of adolescent obesity on educational attainment is not clear. The objectives of our study were to determine whether adolescent obesity is associated with college degree attainment and how this association may have changed over time. We used data from a contemporary national cohort of over 4,000 persons who were adolescents (aged 14–18) in 1997 to assess the relationship between adolescent obesity and education. To assess for changes in this relationship over time, we also analyzed an older, similarly structured cohort of over 3,000 persons who were adolescents (aged 16–18) in 1981. Our primary outcome was college degree completion. We found that in the older cohort (adolescents in 1979), there were no differences in college degree attainment by adolescent weight status before and after adjustment. However, unadjusted analysis of the contemporary cohort (adolescents in 1997) demonstrated that those who were normal weight as adolescents had a higher prevalence of college degree attainment at follow-up compared to obese adolescents (24% vs. 10%). After adjustment for socio-demographic variables (age, sex, race, height, parental income-to-poverty ratio, parental education, aptitude test scores), obese adolescents were less likely to have attained a college degree compared to normal weight peers (adjusted risk ratio 0.61 95% confidence interval 0.38–0.83). Expectations for a future college degree did not vary by weight status and did not explain this observation. In conclusion, adolescent obesity is associated with lower likelihood of college completion. This relationship was not observed in an older cohort of adolescents.