We used a racially/ethnically diverse sample of 9th and 10th grade males and females to examine the relationships between maternal and paternal problematic substance use and adolescent substance use and to determine whether parental monitoring and parental closeness mediated these relationships. We also examined parental monitoring and parental closeness as mediators in the same model, taking into consideration their unique impact on adolescent substance use for mothers and fathers separately. We also examined six different substances that adolescents may have used in their lifetime, and determined whether these relationships differed on gender, race/ethnicity, or living arrangement.