National reports recognize a growing gender gap in postsecondary enrollment as a major challenge impacting the lives of young men, particularly African Americans. Previous gender and race specific research is largely inconclusive. It is, for example, unclear from previous research how persistent the gender gap is across various school contexts, student demographics, and process characteristics. Drawing data from National Educational Longitudinal Study, the present study uses Hierarchical Generalized Linear Modeling (HGLM) to examine both student and school level characteristics that explain variations in college enrollment among African American men and women (with Caucasians included as a contrast group). Results showed that student level characteristics including gender, socioeconomic status, and race were all significant predictors of postsecondary enrollment. Furthermore, home process characteristics (including students' consistency of postsecondary expectations and parental involvement) significantly explained college enrollment when controlling for student home background factors. When considering school level variables, only the percentage of students receiving free or reduced lunch and the percentage of minorities in the school were significant predictors of college enrollment above and beyond what was contributed at the student level, that is, student background and home process factors. (Contains 6 tables and 1 figure.)