Adolescence is a critical developmental period characterized by neurobiological changes and exposure to novel experiences. According to the Center for Disease Control, approximately 70% of adolescent deaths in the United States are due to risky behaviors such as reckless driving and risky sexual behavior (Kann et al., 2016). In order to better understand what drives adolescent risk-taking, the current studies utilized an interdisciplinary approach, which combined behavioral economic models and functional magnetic resonance imaging (fMRI) to understand neurobehavioral mechanisms of risky choice. The focus of the current studies is to investigate the extent to which neurobehavioral mechanisms of risky choice change across adolescence, and to identify individual differences that explain real-world risky behavior. In Study 1, we show that behavioral sensitivity to risk and neural correlates of risk processing change across a critical period of adolescence. Importantly, our results indicate that individual differences in neural, not behavioral risk sensitivity are predictive of future engagement in health risk behaviors. In Study 2, we examined the relation between inter-individual differences in adolescent expectations of valued rewards and self-reported risky behavior using an adapted behavioral economic model. Implications and future directions for adolescent risky decision-making are discussed.