Decades of research on the effects of media violence have examined associations between viewing aggressive material in the media and aggression and prosocial behavior. However, the existing longitudinal studies have tended to exclusively examine aggression and prosocial behavior as outcomes, with a limited range of potential mediators. The current study examines associations between playing violent video games and externalizing and prosocial behavior over a 5-year period across adolescence. Additionally, the study examines potential mediators of these associations, including empathic concern, benevolence, and self-regulation. Participants included 488 adolescents (Mage of child at Wave 1 = 13.83, SD = 0.98) and their parents, who completed self- and parental measures at three different time points, each 2 years apart. Results revealed that early exposure to video game violence was indirectly associated with lower levels of prosocial behavior as mediated by lower levels of benevolence. Additionally, early video game violence play was associated with higher levels of externalizing behavior at the cross-sectional level, but not 5 years later. Implications of results for adolescents and parents are discussed. (PsycINFO Database Record