Experiencing racial discrimination is a common and chronic stressor for African Americans. Despite documentation of the negative effects of perceived racial discrimination on individual health outcomes, less is known about these effects in the family context. As stress exposure can be a shared experience, one family member's experience with racial discrimination may not only compromise their mental health, but also have negative mental health implications for other family members. Using data from 401 adolescents and their caregivers from the Project on Human Development in Chicago Neighborhoods, we examined associations between racial discrimination and depressive symptomology in the African American family context. In particular, we assessed the extent to which primary caregivers' experiences of racial discrimination are related to their own and their adolescents' reports of depressive symptoms as well as how adolescents' experiences of racial discrimination are associated with their own and their primary caregivers' reports of depressive symptoms. We also explored variations of this process as a function of adolescent gender and family household income. Findings were that the more adolescents experienced racial discrimination, the more depressive symptoms they reported. Similar results for their primary caregivers were found—the more primary caregivers experienced racial discrimination, the more depressive symptoms they reported. However, when examining variations based on adolescent gender, we found that in addition to individual effects of racial discrimination and depressive symptoms, primary caregivers' experiences of racial discrimination were associated with more depressive symptoms for female adolescents and for families with lower household income. Findings suggest the need to examine within-group variability as it pertains to race-based stressors and mental health in African American families.