Elevated rates of risky behavior among Latino youth have been linked to features of acculturation such as discrepant rates of acculturation between parents and adolescents. This study examined how parent-adolescent mainstream and Mexican cultural gaps are differentially related to adolescent risky behavior through family conflict, parental monitoring, and parental involvement among Mexican immigrant families. Contrary to the acculturation gap–distress hypothesis, family conflict did not mediate the relationship between acculturation gaps and adolescent risky behavior. Whereas the mainstream cultural gap was associated with less risky adolescent behavior through increased parental monitoring and involvement, the opposite relationship emerged for the Mexican cultural gap. Findings are discussed in relation to the acculturation gap–distress model and the broader parent-child relationship context. Findings illuminate the practical, theoretical, and empirical importance of recognizing Mexican-heritage youth as embedded within an influential family milieu situated in a culturally plural context.