Using data from the National Educational Longitudinal Study (NELS), this article investigates a number of hypotheses used to explain the relationship between family structure and adolescent drug use. In particular, using linked community-level data, an explicit examination of hypotheses drawn from a community-context model is conducted. These hypotheses posit that the impact of family structure on adolescent behavior is, in part, explained by the different types of communities within which families reside and that community characteristics moderate the impact of family structure on drug use. The results of multilevel regression models fail to support these hypotheses; adolescents who reside in single-parent or stepparent families are at heightened risk of drug use irrespective of community context. Moreover, adolescents who reside in single father families are at risk of both higher levels of use and increasing use over time. A significant community-level effect involves jobless men: Adolescents are at increased risk of drug use if they reside in communities with a higher proportion of unemployed and out-of-workforce men.