"High-risk" adolescents with maladaptive behavior histories and control adolescents (15-17 years of age) participated in a laboratory experiment that measured aspects of risk-taking behavior. High-risk adolescents had behavioral profiles entailing combinations of past substance use disorder, early onset substance use, conduct disorder, criminal history, and dropping out of school. A risk-taking task presented participants with "risky" and nonrisky response options. The risky response option offered a low probability of a large monetary reward or a high probability of a smaller monetary loss and resulted in a net loss of monetary earnings. The nonrisky option protected current earnings. High-risk adolescents chose the risky option more often, had lower overall earnings, and were more likely to persist in making (losing) risky responses following a single gain on the risky option. The data replicate previous findings with high-risk adults.