The objective of the present study was to examine psychosocial correlates of diverse health-compromising behaviors among adolescents of different ages. The study population included 123,132 adolescents in sixth, ninth and 12th grades. Psychosocial correlates of substance abuse, delinquency, suicide risk, sexual activity and unhealthy weight loss behaviors were examined. Risk-taking disposition was significantly associated with nearly every behavior across age and gender groups. Other consistent correlates included sexual abuse and family connectedness. Correlates of health-compromising behaviors tended to be consistent across age groups. However, stronger associations were noted between sexual abuse and substance use for younger adolescents, and risk-taking disposition and school achievement were stronger correlates for older youth. The results suggest the presence of both common and unique etiological factors for different health-compromising behaviors among youth. The results emphasize the importance of focusing on positive 'risk-taking' experiences for youth in prevention programs; being sensitive to possible sexual abuse experiences among both female and male adolescents in health-care consultations; integrating strategies for improved family connectedness into health promotion efforts; and making school relevant for all adolescents.