Despite known adverse causal effects of cigarette smoking on mental health, findings for the effects of adolescent cigarette smoking on later depression and socioeconomic status remain inconclusive. Previous studies have had shorter followup periods and did not have a representative portion of the African American population. Using an analytical method that matches adolescent smokers with nonsmokers on childhood and background variables, this study aims to provide evidence on the effects of adolescent regular smoking on adult depression and socioeconomic status. Our longitudinal study is from the Woodlawn Study that followed 1,242 African Americans in Chicago from 1966-1967 (at age 6-7) through 2002-2003 (at age 42-43). We used a propensity score matching method to find a regular and a non-regular adolescent smoking group with similar childhood socioeconomic and family background and first grade academic and behavioral performance. We compared the matched samples to assess the longitudinal effects of adolescent smoking on adult outcomes. Comparing the matched 199 adolescent regular smokers and 199 non-regular smokers, we found statistical support for the effects of adolescent cigarette smoking on later educational attainment (OR, 2.13; 95 % CI, 1.34, 3.39) and long-term unemployment (OR, 1.74; 95 % CI, 1.11, 2.75), but did not find support for the effects on adulthood major depressive disorders. With a community population of urban African Americans followed for 40 years, our study contributes to the understanding of the relationships between adolescent smoking and later educational attainment and employment.