Juvenile violence is a phenomenon that consistently garners great attention in the media, the public, and across a multitude of academic disciplines. A growing body of literature in developmental and lifecourse criminology has called for innovative research to further investigate the causes and correlates of serious juvenile offenders. Toward this end, the present study uses prospective, longitudinal data from the Pittsburgh Youth Study (PYS) to gauge the temporal impact of childhood and adolescent mental health problems on the development of serious offending behaviors in boys. Borrowing largely from the work of Achenbach and colleagues (2001), data from parent and teacher reports of psychopathological problems were used to create DSM-oriented scales for Oppositional Defiant, Attention-Deficit/Hyperactivity, Anxiety, and Affective Problems. These scales offer a more continuous form of measurement than DSM diagnoses and allowed for distinctions between normal, borderline, and clinical levels of mental health problems. Forward-step logistic regression analyses indicated that three different teacher-reported DSM-oriented mental health problems emerged at three different stages of development as significant predictors of serious violence over the lifecourse. The significant substantive, methodological, and public policy implications of the study are discussed.