This study aims to explore the utility of the resilient, overcontrolled, and undercontrolled personality prototypes in discriminating adolescents with respect to their academic and social functioning and success. One-hundred and twelve male and 95 female Italian adolescents (mean age = 17 years old) participated in the study and filled out a number of self-report questionnaires aimed at assessing the Big Five personality traits, academic and social functioning indicators, and internalizing and externalizing problems. Prototype membership, corresponding to the resilient, overcontrolled and undercontrolled types, was derived from cluster analysis of the Big Five self-ratings. The three prototypes clearly differed in terms of their academic and interpersonal functioning and problem behavior. Resilient adolescents showed higher academic success and better relationships with peers; whereas undercontrollers and overcontrollers both reported more internalizing and externalizing problems, as well as having more deviant friends who both are drug addicts and steal. (Contains 5 tables and 1 figure.)