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This study examines generational patterns of parenting styles, the relationships between parenting styles and adolescent well-being among youth of Mexican origin, and the role of generational parenting style patterns in explaining generational patterns in youth behavior (delinquency and alcohol problems) and psychological well-being (depression and self-esteem). This study uses two waves of data from the National Longitudinal Study of Adolescent Health (Add Health). The proportion of teens with permissive parents increased with generation; other parenting styles declined. The rate of youth with behavioral problems increased with generation. Self-esteem improved with generation; depression scores did not. Bivariate generational patterns of behavioral and psychological outcomes are a function of the patterns seen for youth with permissive parents, coupled with the increase in the proportion of permissive parents with each successive generation. In contrast, these outcomes did not worsen with generation for youth with authoritative parents.