Individual differences, particularly callous and unemotional (C&U) traits, and parenting practices are some of the strongest predictors of externalizing behavior in adolescents. However, findings on the associations between C&U traits, parenting, and externalizing behaviors have been mixed, with studies often utilizing single scores to represent these multidimensional constructs. The current study used a developmental-contextual framework to examine how dimensions of C&U traits predict aggressive and non-aggressive rule-breaking behaviors through positive and negative parenting practices. The study used archival data from 174 pairs of adolescent males, ages 11-16 years old, and their mothers. Results showed that C&U traits influenced externalizing behaviors through parenting practices. Findings also showed specificities among these relationships. Particularly, the associations between Uncaring and aggressive, as well as non-aggressive rule-breaking, behaviors was mediated by negative parenting, whereas the association between Unemotional and rule-breaking behaviors was mediated by positive parenting practices. Research and clinical implications are discussed.