Links between parental personality, parenting, and adolescent behavior have been well established. However, extant research is limited by the sole focus on parental Big Five personality, and not taking home and family context into account. These gaps were addressed in two studies. In study 1, context, parental personality, and their interactions were examined as predictors of parenting in separate mother and father models (parents only). In study 2, context, parental personality, and parenting were examined as predictors of adolescent behavioral outcomes (parent–adolescent dyads). Parents (N = 283, 45.6% mothers, Mage = 45.51 years) completed assessments of socioeconomic status (SES), adverse childhood experiences (ACEs), personality (Big Five, Dark Triad), and parenting. Adolescents (N = 257, 51.4% female, Mage = 13.65 years) completed an assessment of behavior. Parent Dark Triad domains explained more variance in parental warmth and hostility than the Big Five, but equivalent variance in adolescent behavior. SES interacted with maternal personality, whereas ACEs interacted with paternal personality, to predict parenting behavior. The results showcase the importance of assessing a wider spectrum of parental personality, and examining contextual factors, in affecting adolescent development.