Considerable research in the United States has established that adolescent antisocial, aggressive, and attention problem behaviors negatively influence adolescents' ability to become productive members of society. However, little is known about the development of these problems among adolescents in other countries. This study contributes to our understanding of personality and parenting factors associated with adolescent problem behaviors using an international sample. Data are from a National Institute on Drug Abuse-funded study of 884 community-dwelling adolescents in Santiago, Chile, of mid-to-low socioeconomic status. Results reveal that rule-breaking and aggressive behaviors were both associated with greater levels of adolescent drive but lower levels of parental monitoring and positive parenting by both parents. Adolescents who reported more attention problems were more likely to exhibit driven behavior and more behavioral inhibition and to report lower levels of parental monitoring and positive parenting by mother and father. Results of interactions revealed that the influences of positive parenting and parental monitoring on adolescent aggressive behaviors varied as a function of the gender of the adolescent. Helping parents build on their parenting skills may result in important reductions in adolescent problem behaviors among U.S. and international adolescents.