This study of over 1,000 adolescents focused on common and distinctive correlates of four subgroups—no problem, depressed only, heavy drinking only, and mixed (depressed and heavy drinking). Correlates were evaluated from the domains of personal dispositions (e.g., temperament), interpersonal relations (e.g., parent and peer), stressful life events, and other problem behaviors (e.g., delinquency, substance use). The no-problem subgroup differed from the other three subgroups in the direction of healthier functioning on almost all measures. The mixed subgroup reported the most pervasive, low levels of functioning, with the highest levels of childhood externalizing problems and stressful life events, the lowest levels of family social support, and high levels of delinquency and substance use. The depressed-only subgroup reported a more internalized pattern characterized by childhood avoidance problems, a difficult temperament (e.g., inflexibility, withdrawal, low task orientation), interpersonal stressors, and poor coping strategies. The heavy-drinking-only subgroup was characterized by higher drinking levels by primary caregivers and lower levels of family cohesion as reported by primary caregivers. The 1-year prospective findings were generally consistent with the concurrent findings in that variables that were associated with transitions toward and away from depression and heavy drinking were associated with specific transitions (e.g., childhood externalizing problems were associated with the transition from no problem to heavy drinking).