African American male youth experience disproportionately higher levels of violence. We examined parental depression among African American mothers and nonresident fathers on parenting stress and school involvement in their adolescent sons' school connectedness and violent behaviors. Using a longitudinal study design, parent factors were assessed when sons were 9 years old on youth outcomes at age 15. We found that maternal depression was associated with maternal stress, and maternal stress was indirectly associated with sons' violent behaviors through school connectedness. School involvement among nonresident fathers was positively associated with sons' school connectedness, which was linked to less youth violent behaviors. Maternal stress and nonresident fathers' school involvement are influential for understanding youth violence. Future interventions should incorporate a more nuanced approach when including family factors.