Guided by social development constructs, this article investigates race and gender differences in the initiation of various types of delinquent behavior and alcohol and marijuana use among African American and Caucasian adolescents in grades 7 through 12. In addition, this study examined the potential direct or indirect effects of parental supervision, clarity of family rules, and association with delinquent peers. Results from the longitudinal analyses indicate that boys were significantly more likely to initiate delinquent acts throughout adolescence, but racial differences indicated by main effects were identified in fewer delinquent outcomes. Results also suggest no gender differences in the initiation of alcohol and marijuana use during adolescence; however, there was a negative and significant effect for African Americans and the initiation of alcohol use. Interactions between race and gender for each of the outcomes were also statistically significant in predicting some delinquent behaviors. These findings have implications for prevention and intervention activities in multiple settings.