Using data from grandparents (G1), parents (G2), and children (G3), this study examined continuity in parental monitoring, harsh discipline, and child externalizing behavior across generations, and the contribution of parenting practices and parental drug use to intergenerational continuity in child externalizing behavior. Structural equation and path modeling of prospective, longitudinal data from 808 G2 participants, their G1 parents, and their school-age G3 children (n = 136) showed that parental monitoring and harsh discipline demonstrated continuity from G1 to G2. Externalizing behavior demonstrated continuity from G2 to G3. Continuity in parenting practices did not explain the intergenerational continuity in externalizing behavior. Rather, G2 adolescent externalizing behavior predicted their adult substance use, which was associated with G3 externalizing behavior. A small indirect effect of G1 harsh parenting on G3 was observed. Interparental abuse and socidemographic risk were included as controls but did not explain the intergenerational transmission of externalizing behavior. Results highlight the need for preventive interventions aimed at breaking intergenerational cycles in poor parenting practices. More research is required to identify parental mechanisms influencing the continuity of externalizing behavior across generations.