The purpose of this study was to allow African American males across generations to share their perceptions of the factors that affected their schooling experiences and influenced their achievement in and beyond school. Individual interviews were conducted with men and boys within the context of their home environment; outside of the schools the boys attended. The participants' schooling experiences call for establishing a model of collective achievement that captures and delineates the engagement and investment of the multiple stakeholders involved in their education. Such a model will bring about a higher level of multiple stakeholder accountability that would likely improve students' schooling experiences and increase the academic and life outcomes for African American males. (Contains 2 tables.)