This study investigated the relationship of terminal core values to delinquency, substance use, and sexual behavior in a sample of 544 high school students. Students were classified according to their dominant value, and comparisons were made in regard to thirty-one indicators of delinquency, substance use, and sexual activity. As predicted by social control and strain theories, groups valuing fun/enjoyment and security were strongly identified with delinquency and substance use. Groups valuing self-respect, being well-respected, sense of accomplishment, warm relationships with others, and sense of belonging exhibited low frequency of delinquent behavior and substance use. Sense of belonging tended to be related to lower sexual activity, while warm relationships with others and being well-respected were associated with the most sexual activity. Gender differences in problem behaviors were also explored. The implications for theory and intervention are discussed, and values self-confrontation is proposed as a method for reducing problem behaviors.