The central question addressed in this study was whether upper class, suburban teenagers can engage in various problem behaviors and still maintain adequate academic grades, because of environmental safety nets, unlike their low-income, inner-city counterparts. Three problem behavior dimensions were assessed among tenth graders, that is, substance use, delinquency, and low school engagement. Academic achievement was assessed in terms of grades across four major subjects. Variable-based analyses indicated unique links with grades for self-reported delinquency and school disengagement in high- and low-income samples, but for substance use only among the former. Person-based analyses showed that in both schools, grades were clearly compromised among youth with disturbances in all three problem domains. In addition, in the suburban school only, grades were low in the cluster characterized chiefly by high substance use. Results are discussed in terms of stereotypes regarding risks (or lack thereof) stemming from families' socioeconomic status; implications for theory and interventions are also considered.