The aim of the research was to investigate the influence of gender, exposure to community violence, and parental monitoring upon antisocial behavior and anxiety/depression in adolescence. Involved in the study were 489 adolescents (290 males and 189 females) from 4 secondary schools in the city of Naples, Italy. The age of participants ranged from 16 to 19 (mean age = 17.53, standard deviation = 1.24). All were in the 3rd (11th grade) or 5th year (13th grade) of high school. Self-reported measures were used to assess antisocial behavior, symptoms of anxiety/depression, parental monitoring and exposure to community violence as a victim or as a witness. First of all we tested, through a hierarchical multiple regression, the independent contribution of gender, exposure to community violence and parental monitoring upon antisocial behavior and symptoms of anxiety/depression; then we tested the moderating role of gender and parental monitoring on the negative effects of exposure to violence. The results show that male gender, high level of exposure to community violence (both as a victim and a witness), and low level of parental monitoring predict a higher involvement in antisocial behavior. Female gender, being a victim and low level of parental monitoring predict symptoms of anxiety/depression. Furthermore, parental monitoring and gender play a moderating role, minimizing or amplifying the negative effects of exposure to community violence. The results of the research suggest that a similar pattern of risk and protective factors can give rise to multiple paths of adaptive or maladaptive development.