This study examined the interplay of parental racial-ethnic socialization and youth multidimensional cultural orientations to investigate how they indirectly and directly influence youth depressive symptoms and antisocial behaviors. Using data from the Korean American Families (KAF) Project (220 youths, 272 mothers, and 164 fathers, N = 656), this study tested the relationships concurrently, longitudinally, and accounting for earlier youth outcomes. The main findings include that racial-ethnic socialization is significantly associated with mainstream and ethnic cultural orientation among youth, which in turn influences depressive symptoms (but not antisocial behaviors). More specifically, parental racial-ethnic identity and pride discourage youth mainstream orientation, whereas cultural socialization in the family, as perceived by youth, increases ethnic orientation. These findings suggest a varying impact of racial-ethnic socialization on the multidimensional cultural orientations of youth. Korean language proficiency of youth was most notably predictive of a decrease in the number of depressive symptoms concurrently, longitudinally, and after controlling for previous levels of depressive symptoms. English language proficiency was also associated with a decrease in depressive symptoms, implying a benefit of bilingualism.