Research on early childhood predictors of violent behaviors in early adulthood is limited. The current study investigated whether individual, family, and community risk factors from 18 to 42 months of age were predictive of violent criminal arrests during late adolescence and early adulthood using a sample of 310 low-income male participants living in an urban community. In addition, differences in trajectories of overt conduct problems (CP), hyperactivity/attention problems (HAP), and co-occurring patterns of CP and HAP from age 1½ to 10 years were investigated in regard to their relationship to violent and nonviolent behaviors, depression, and anxiety at age 20. Results of multivariate analyses indicated that early childhood family income, home environment, emotion regulation, oppositional behavior, and minority status were all significant in distinguishing violent offending boys from those with no criminal records. In addition, trajectories of early childhood CP, but not attention deficit hyperactivity disorder, were significantly related to self-reports of violent behavior, depressive symptoms, and anxiety symptoms. Implications for the prevention of early childhood risk factors associated with adolescent and adult violent behavior for males are discussed.