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This study investigated significant relationships between youth assets and youth alcohol, tobacco, and drug use that differ according to family structure (one- or two-parent households). Data were collected from a randomly sampled inner-city population (n=1,256 teenagers and 1,256 parents of the teenagers) using in-home, in-person interviews. Logistic regression analyses, stratifying by one- and two-parent household status, were conducted with nine youth assets as the independent variables and youth alcohol, tobacco, and drug use as the dependent variables. Results indicated that the associations between assets and risk behaviors varied depending upon whether the youth lived in one- or two-parent households. Continued research is warranted to further investigate associations among family structure, youth assets, and youth risk behaviors.