Mental health problems have long been linked to antisocial behaviors. Despite an impressive body of literature demonstrating this relationship and claims that comorbidity matters, few studies examine comorbidity using multiple distinct mental health indicators, with most studies instead adopting single or composite mental health measures. This study tested separate and comorbid effects of five DSM-oriented mental health issues on self-reported violence using a community-based sample of Chicago youths from the Project on Human Development in Chicago Neighborhoods. Moreover, it utilized both primary caregiver and youth self-reports of psychopathology across four developmental stages of childhood and adolescence. When examined separately, the results indicated affective/depressive, anxiety, attention deficit hyperactivity, and oppositional defiant/antisocial personality problems independently predicted violence. When considering comorbidity, however, only oppositional defiant and antisocial personality problems significantly predicted violence at any stage, regardless of informant type. Implications for future studies and policy are discussed.