Researchers have found mixed support for documenting whether work is protective or harmful during adolescence. This study examined the association between work and problem behaviors among African American youth (N = 592; 53% female; M = 14.8 years, SD = 0.60) followed from mid-adolescence to young adulthood over eight Waves (90% response rate over the first four Waves and a 68% response rate across all eight Waves). We explored three competing operationalizations of work: work history (never worked, worked), work intensity (no work, 20 h or less, and 21 h or over), and work trajectories (never worked, episodic work, stopped working, late starter, and consistent worker). Non-working youth reported higher marijuana use during young adulthood than their working counterparts. Nonworkers reported lower self-acceptance during young adulthood than those working greater number of hours per week. Differences in work trajectories for cigarette use, depression, and anxiety during adolescence imply that when and for how long youth work are also important factors to explore. Our findings lend tentative support to the work benefits perspective and suggest that the association between work and problem behaviors may depend on the work measure used. We discuss the implications of employing different work measures in adolescent research.