The purpose of this study was to describe the academic achievement and attitudes toward school of middle school students relative to the Black–White achievement gap and hip hop music and culture. Achievement data were collected from the Connecticut Mastery Test scores of one suburban district‘s middle school students. This mixed-method study collected qualitative and quantitative data from the 7th- and 8th-grade students using an in-school survey that asked questions about school and hip hop music and culture. Students also completed a take-home log to record how long they participated in various after-school activities, including listening to music. There was not a significant amount of data collected concerning the amount of time students listen to hip hop music in order to determine if this could be a factor in lower achievement levels for hip hop listeners. The results of this study showed that students who listen to hip hop music did not meet goal on all three state standardized tests, and consequently, achieved at a lower level than their non-hip-hop-listening peers regardless of race. This research also examined how the negative lifestyles portrayed by hip hop artists influence the attitudes of students toward their school and learning. When asked to describe the term acting Black, most student responses were derived from negative images and concepts about African Americans that they are exposed to through listening to hip hop music and watching hip hop videos.