The goal of the study was to assess individual differences among adolescents regarding risk-taking behavior in the laboratory. The second aim was to evaluate whether the laboratory-based risk-taking behavior is associated with other behavioral and psychological measures associated with risk-taking behavior. A total of 82 adolescents with no personal history of psychiatric disorder completed a computerized decision-making task, the Wheel of Fortune. On the basis of the choices made between clearly defined probabilities and real monetary outcomes, this task assesses risk preferences when participants are confronted with potential rewards and losses. The participants also completed a variety of behavioral and psychological measures associated with risk-taking behavior. Performance on the task varied on the basis of probability and anticipated outcomes. In the winning sub-task, participants selected low-probability-high-magnitude reward (high-risk choice) less frequently than high-probability-low-magnitude reward (low-risk choice). In the losing sub-task, participants selected low-probability-high-magnitude loss more often than high-probability-low-magnitude loss. On average, the selection of probabilistic rewards was optimal and similar to performance in adults. There were, however, individual differences in performance, and one-third of the adolescents made high-risk choice more frequently than low-risk choice while selecting a reward. After controlling for sociodemographic and psychological variables, high-risk choice on the winning task predicted "real-world" risk-taking behavior and substance-related problems. These findings highlight individual differences in risk-taking behavior. Regarding validity of the Wheel of Fortune task, the preliminary data suggest that it might be a valuable laboratory tool for studying behavioral and neurobiological processes associated with risk-taking behavior in adolescents.