The purpose of this study was to examine the different perceptions that shape African American male high school students' understanding of their academic experiences that lead to their success or lack of success in school. In addition, the study identified factors that explain the underachievement of African American male students who are academically capable, have sufficient financial resources, and adequate support from home. The qualitative, multiple case study design was used to study the phenomenon, African American male underachievement. The researcher interviewed six African American male students in grades 11 and 12 from a high school in the rural South. The interviews were recorded onto a digital recording device and transcribed at a later time. Other sources of data collection were observation notes and documents pertaining to student academic performance. The transcripts, observation notes, and documents were analyzed using open coding to identify emergent themes. Data analysis revealed three major findings contributing to the underachievement of academically capable African American males at the high school level. The major findings were as follows: poor study habits, difficulty transitioning from middle school to high school, and a culture of complacency. The findings suggest that in order to motivate African American males who have the intellectual ability, home support, and sufficient financial resources yet underachieve, schools must implement a positive school culture that supports the academic success of all students and train teachers to implement strategies to support and educate the African American male student. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]