By most measures of success--e.g., academic Grade Point Average (GPA), graduation rates, participation in extracurricular and civic activities, and college enrollment--adolescent males are less successful than females. Young males are falling behind in reading and writing and are more likely to be involved in truancy, violence, crime, suicide, and substance abuse. While the nation mobilized to address historical gender discrimination issues for females since the 1970s, there has not been a similar effort mounted to assist adolescent males. The trends alluded to in the previous paragraph have begun to be recognized by popular-press authors. Some have begun to refer to contemporary adolescent males as "lost boys". To date, however, the academic literature on this topic has been limited. This study begins to systematically research the characteristics associated with the lost-boys phenomenon from the perspective of the high school aged males themselves. The purpose of the research was to begin to create grounded theory about the lost-boy phenomenon and identify the common characteristics and differences noted in a small sample of adolescent males who exhibit the syndrome. The study employed qualitative research methods to provide richness of detail. Case studies of eight high school males identified as underachievers by school teachers and administrators are presented. The findings suggests the following: (a) the adolescent males in this study had few, if any, mentors, heroes, and people other than family and peers they ask for advice; (b) even in this study's small sample, there was variation in the quality and quantity of male social relationships and this variation appeared to impact academic performance; (c) because of moving and other disruptions, supportive relationships often were difficult to establish; (d) some interviewees indicated that being asked introspective-oriented questions during interviews helped them improve their academic performance; (e) there were no programs to assist underachieving adolescent males identified in this study; (f) while ethnicity is factor in forming relationships, and therefore, may indirectly impact academic performance, this study's diverse (but admittedly small) sample suggests that there are common elements in the modern adolescent male experience that transcend ethnicity, socio-economic status, and familial influences. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]