Previous literature suggests that the adolescent at risk to engage in substance use and other negative health-related behaviors is deviant in a negative sense (i.e., rebellious, antisocial, and alienated from traditional institutions). However, some researchers have distinguished between two types of deviance-a true autonomy and independence that is more positive and constructive, and a reactant "anticonformity" that is more negative and destructive. The current study assessed the roles of both constructive and destructive deviance in adolescent cigarette smoking and positive health-related behaviors. Adolescents who were constructively deviant engaged in higher levels of health-protective behaviors. Moreover, constructive deviance was an independent predictor of both cigarette smoking and positive health behaviors over and above the effects of traditional negative deviance indicators. These data suggest that constructive deviance is not a competing model to more traditional notions, but that it is an additional possible pathway into adolescent positive and negative health behaviors.