This study examined the relationship of sex-role typology, medical and psychiatric symptomatology, and personality functioning in adolescents. Seventy-nine males and 101 females with an average age of 18.3 were administered the Bem Sex Role Inventory (BSRI), Offer Self Image Questionnaire (OSIQ), Self Rating Depression Scale (SRDS), and Cornell Medical Index (CMI). In comparison to males, females reported significantly more medical and psychiatric symptomatology, including depression. Females were also found to have more concern and empathy for others and a better developed superego. They reported greater involvement in making future plans and were more conservative in their sexual attitudes. Sex-role typology yielded no significant differences on the medical and psychiatric scales, but consistent differences were found on the OSIQ, a measure of adolescent personality functioning. In general, the results indicated that androgynous teenagers in every case differed from the undifferentiated ones, with the masculine and feminine groups occupying a mid-position. Androgynous individuals always showed a more favorable adjustment. Undifferentiated individuals had a poorer defensive structure, less adequate coping mechanisms and affective integration, more confusion about body boundaries, and more difficulty in object relations. Androgynous individuals, in short, possessed adaptive capabilities and resources, such as effective coping techniques, emotional integration, communication skills, and a well-defined self-concept (i.e., ego strength and a high level of psychological integration). Since these results were obtained on a measure constructed solely to assess adolescent functioning, it seems possible to screen and identify adolescents who may be entering adulthood lacking the emotional, social, and occupational capacity to function in an optimal fashion.