Although explanatory models of adolescent risk behavior have predominantly focused on adolescents' limited ability to self-regulate impulsive and/or reward-driven behavior (reactive risk behavior), recent arguments suggest that a significant proportion of adolescent risk behavior may actually be strategic and planned in advance (reasoned risk behavior). The present study evaluates hypothesized predictors of reasoned versus reactive risk behavior using self-reported and neurocognitive task data from a large, diverse adolescent sample (N = 1266 participants; N = 3894 risk behaviors). Participants' mean age was 16.5 years (SD = 1.1); 56.9% were female, 61.9% White, 17.1% Black, 7.0% Hispanic, and 14.1% other race/ethnicity; 40% were in 10th grade, 60% in 12th grade. As hypothesized, reasoned risk behavior (compared to reactive risk behavior) was associated with higher levels of sensation seeking, better working memory, greater future orientation, and perceiving risk behavior to be more beneficial than risky. These results support the distinction between reasoned and reactive risk behavior as meaningful subtypes of adolescent risk behavior and challenge prevailing frameworks that attribute adolescent risk behavior primarily to poor response inhibition.