Background/Context: Today, in the era of the first African American president, approximately one third of all African Americans live in suburban communities, and their children are attending suburban schools. Although most research on the education of African American students, particularly males, focuses on their plight in urban schooling, what occurs in suburban schools is also in need of examination. Purpose/Focus of Study: This research focused on the lived experiences of 4 middle-class African American male students attending affluent White suburban schools. Through vignettes focusing on their various experiences and recollections, this study provides a preliminary snapshot, part of a larger study, of the schooling environments in the life stories of middle-class Black suburban youth. Research Design: Qualitative methodology was used to explore the life histories of the 4 African American males. Each student participated in a tape-recorded interview to examine what it meant to grow up in White upper-middle-class suburban communities and to matriculate within suburban district schools from elementary through high school. Findings/Results: The salient themes that emerged from the rich, interactive conversations and dialoguing address issues related to disillusionment and resilience; the presence or absence of racism; academic pressures; social bonding and identity development in racialized social and academic settings; and the gatekeeping role of athletics. Conclusions/Recommendations: Suburban education may not be the panacea that African American families had hoped. The socioeconomic status of African American families who live in affluent White suburban communities may not be enough to mitigate against the situated "otherness" that Black students--in this case, males--experienced in affluent White suburban schools. More research is needed to understand the positionality of Black male students in suburban schools; relationships between suburban Black adolescent males and females; school life beyond athletics; the role of the family and community in combating racism and otherness; and how student agency can be a force for change.