The study analyzed data from the Youth Development Study (YDS), a longitudinal survey of adolescents and their parents in St. Paul, MN. Beginning in 1988, a randomly selected panel of 1,000 St. Paul high school students completed follow-up surveys each year to assess the effects of adolescent work on mental health, educational attainment, work attitudes, and developmental maladjustment. Valid work-dimension and deviance scores were available for 652 adolescent workers. Three indicators of adolescent deviance were considered: school deviance, alcohol use, and arrest. These variables were used to examine the robustness of the work effects. For 12th-grade youth, school deviance, alcohol use, and arrest were lowest among adolescents whose jobs supported rather than displaced academic roles and provided opportunities for them to learn new tasks and gain new knowledge. In contrast, many qualities of work considered desirable for adults, such as autonomy, social status, and wages, apparently increased delinquency in adolescence. These findings suggest the importance of matching employment opportunities to the ages of the workers. Future research should focus on identifying the particular life-course stage when the effects of wages, status, and autonomy reverse course and begin to reduce rather than increase crime and deviance. 8 tables, 1 figure, 7 notes, and 49 references