This article considers the complex nature of the experiences of school for six young African-American men who were from different social class backgrounds and attended four different schools. Through extended interviews over the course of the 1992-1993 school year, I learned that while all the young men were committed to acquiring a high school diploma, they simultaneously critiqued aspects of their experiences in school. The critique included the disengaging pedagogy and curriculum they experienced in classrooms and the Eurocentric focus of their history curriculum. Notwithstanding the pattern of critique and accommodation among the young men, there was variation in what they chose to critique and accommodate. My examination of the ways in which they critiqued and accommodated school includes a consideration of the different kinds of choices the young men made, the different kinds of futures they imagined for themselves, their different ideas about what was important to know, and their different meanings of success. I argue that their different meanings of school, schooling, and the diploma in a large measure can be explained through examining their differential access to power and privilege, the ways in which they encountered inequality, and the ways in which they experienced the structure and culture of school. I further argue that the intermingling of interconnected systems of race, class, and gender in the context of their daily school lives can be a powerful explainer of the differences, and at times the similarities, in the meanings they made of school.