Background: Health risk behaviors like substance use (alcohol, tobacco, soft/hard drugs) and risky sexual behavior become more prevalent in adolescence. Children with behavior problems are thought to be prone to engage in health risk behaviors later in life. It is, however, unclear which problems within the externalizing spectrum account for these outcomes. Methods: Three hundred and nine children were followed from age 4/5 years to 18 years (14-year follow-up). Level and course of parent-rated opposition, physical aggression, status violations and property violations were used to predict adolescent-reported substance use and risky sexual behavior at age 18 years. Results: Both level and change in physical aggression were unique predictors of all forms of adolescent health risk behavior. Levels of status violations predicted smoking and soft drug use only, while change in property violations predicted each of the health risk behaviors. The links between opposition and health risk behaviors were accounted for by co-occurring problem behaviors. Conclusions: Of externalizing problems, physical aggression is the best predictor of adolescent substance use and risky sexual behavior from childhood onwards. Possible explanations and implications of these findings, and future research directions are discussed. © 2007 The Authors.