We aimed to analyze the impact of several parenting factors on the relationship between psychopathy and antisocial behavior. Nine hundred youths and their mothers reported on parent–youth interactions, and youth self-report measures of psychopathy, delinquency and violent behavior were taken. Multiple regression was used to test for the significance of interactions between parenting and psychopathy scores. In terms of delinquency, linear interactions between psychopathy and the level of conflict with parents and parents' knowledge of their youths' whereabouts/youths' willingness to disclose information were found based on the data reported by the youths. Data reported by mothers indicated a linear interaction between psychopathy and parents' knowledge/youth disclosure, and a quadratic interaction of conflict with parents. For violence, we used logistic regression models to analyze moderation. No interaction effects between psychopahy scores and parenting factors were found. Youths' reports of high conflict with parents and parents' knowledge/youth disclosure showed to have an impact on violence regardless of the level of psychopathic traits. Implications for the prevention and treatment are discussed.