The school lives of black middle-class males are often overlooked and understudied. An exploration at the intersection of race, class and gender for black middle-class males provides opportunity for a more nuanced understanding of the black male schooling experience. Drawing upon student resistance theories as analytical tools and employing qualitative interpretive methods, this study documented the raced, classed, and gendered approaches to schooling of black middle-class males. In particular, this article highlights the ways in which black middle-class male youth balanced the academic expectations of their parents with the cultural expectations of their peers through tactical acts of resistance and accommodation. Their tempered approach to academic effort, disruption of school processes, and peer validated performances of black masculine cool were just some of the ways they navigated schooling as a site of conflicting cultural expectations. The intent of their resistance and accommodation in school as raced, classed, and gendered bodies present both opportunities and dilemmas for improving black male achievement and middle-class reproduction. (Contains 1 table and 3 notes.)