The present study examined the role of parental rearing behavior in adolescents' risky decision-making and the brain's feedback processing mechanisms. Healthy adolescent participants (n = 110) completed the EMBU-C, a self-report questionnaire on perceived parental rearing behaviors between 2006 and 2008 (T1). Subsequently, after an average of 3.5 years, we assessed (a) risky decision-making during performance of the Balloon Analogue Risk Task (BART); (b) event-related brain potentials (ERPs) elicited by positive (gain) and negative feedback (loss) during the BART; and (c) self-reported substance use behavior (T2). Age-corrected regression analyses showed that parental rejection at T1 accounted for a unique and significant proportion of the variance in risk-taking during the BART; the more adolescents perceived their parents as rejecting, the more risky decisions were made. Higher levels of perceived emotional warmth predicted increased P300 amplitudes in response to positive feedback at T2. Moreover, these larger P300 amplitudes (gain) significantly predicted risky decision-making during the BART. Parental rearing behaviors during childhood thus seem to be significant predictors of both behavioral and electrophysiological indices of risky decision-making in adolescence several years later. This is in keeping with the notion that environmental factors such as parental rearing are important in explaining adolescents' risk-taking propensities.