This research is an interpretive qualitative study that explores the perceptions and perspectives of two generations of African American male students, as related to their educational experiences at the same southeastern New Mexico high school. The central question of this research is, has the educational experience for African American male students (specifically, classroom engagement and teacher interaction) changed in the past 30+ years? Purposeful sampling was employed to obtain research participants for this interpretive qualitative study. Through the triangulation of individual interviews, focus groups, and portraiture, I investigate dynamics within the educational environment that enhance or hinder academic achievement among African American male students. Triangulation of qualitative methods yielded six themes that illuminated perceptions of African American male students regarding barriers and positive influences within the educational environment that shaped their perceptions regarding academic achievement, self-worth, and aspirations toward post-secondary goals. I anchor this research in two theoretical frameworks--Critical Race Theory and Stereotype Threat Theory to evaluate how race might impact participant perceptions and interactions within the educational environment. The research identified that the educational experiences of African American males, as specifically related to classroom engagement and teacher interaction, has not changed over the past 30+ years. However, interpretation of educational experiences and perceptions of the African American male students appear to have shifted from an oppressive group mindset (older generation), to a more liberated, individualistic view (younger generation). Lastly, I discuss implications and recommendations of this study that are directed toward administrative commitment, teacher practices that promote student efficacy, and collaboration with family and community stakeholders to foster an educational environment that supports the diverse needs of African American male students. [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.]