This phenomenological investigation examines the perceptions of the teaching profession as a viable career option by high-achieving high school-aged African American boys. Researchers used random sampling to identify high schools in one large urban school district and criterion sampling to examine the perceptions of 63 African American 11th-grade boys. Participants completed a perceptual analysis inventory, constructed a circle map, sketched an artistic drawing of a classroom teacher, and participated in focus group sessions. Using an explicitation analysis process, three themes emerged as factors that dissuaded participants from considering teaching as a career option: (a) Negative Perceptions of Teachers and Teaching, (b) Schools as Oppressive Institutions, and (c) African American Males as Nonconformists. Recommendations for practice and future research are offered.