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This study examined the associations between parental cigarette smoking and youth externalizing behaviors (i.e., oppositional and conduct problems) both concurrently and 1 year later, and tested whether parental smoking predicted youth externalizing over and above parent psychosocial, family, and demographic characteristics linked to smoking and externalizing behaviors. Data were drawn from the Seattle Social Development Project (SSDP) and The Intergenerational Project (TIP), a prospective longitudinal study aimed toward understanding the intergenerational transmission of substance use, mental health, and risky behaviors. The current study used multilevel modeling to examine both concurrent and lagged associations from 325 families, which included parents and youth (Aged 6–19) across seven waves of data. In concurrent analyses, both parental smoking and several family characteristics independently predicted higher levels of child externalizing behaviors, even after controlling for parent age at child birth and demographic correlates of smoking. However, parental depressive symptoms reduced the association between smoking and externalizing behaviors to nonsignificance in concurrent models. In lagged analyses, only harsh parenting, low monitoring, and low parent-child bonding predicted externalizing behaviors 1 year later; parental smoking did not predict externalizing behaviors over time. Results showed that parental smoking, mental health, parenting, and family relationships all are associated with externalizing problems and constitute potential intervention targets in the short term, though poor parenting and parent-child bonding, rather than smoking, predicted externalizing behaviors over time. The robust association between concurrent parental depressive symptoms and youth conduct problems may suggest prioritizing parental mental health (e.g., via mental health screening) for improving both parent and child well-being.