The present study examined whether combinations of ethnicity, gender, and age moderated the association between perceived discrimination and psychological well-being indicators (depressive symptoms, self-esteem, and life satisfaction) in a nationally representative sample of Black youth. The data were from the National Survey of American Life, which includes 810 African American and 360 Caribbean Black adolescents. The results indicated main effects such that perceived discrimination was linked to increased depressive symptoms and decreased self-esteem and life satisfaction. Additionally, there were significant interactions for ethnicity, gender, and race. Specifically, older Caribbean Black female adolescents exhibited higher depressive symptoms and lower life satisfaction in the context of high levels of perceived discrimination compared with older African American male adolescents. (Contains 4 tables and 2 figures.)