This article reports findings from an ethnographic study of the literacy practices of a group of 11-14 year-old Black males who defined themselves as "the cool kids." The study is framed using theories that view literacy as a social and cultural practice involving multiple sign and symbol systems. Two research questions guided the study: How did coolness relate to literacy among the young men who called themselves "the cool kids," and what symbolic patterns helped to shape these relations? The findings describe how the group's use of language and style involved issues of race, gender, and pop culture and reveal how coolness, as a pop cultural artifact of Black manhood, contributed to the literacy practices of the young men and to the construction of their symbolic selves. These findings contribute to building a theory of Black masculine literacies. (Contains 3 tables and 6 figures.)