The "Brown v. Board of Education" decision provided unrestricted access to educational opportunities for all students. Unfortunately, despite the passing of the 50th anniversary of this landmark decision, academic excellence remains a dream deferred for many Black students when compared to their peers. This disparity, more popularly known as the achievement gap, has garnered considerable attention in the educational research literature and has been characterized as "the most significant educational problem in the U.S." Many educational researchers have written on the topic of the achievement gap between Black students and their peers; however, only a few have focused on the participation gap explicitly. According to these educational researchers, many complex cultural variables might contribute to the widespread disparities. For example, researchers have contributed cultural concepts such as "acting White" and "acting Black" to the gifted education research literature. Such concepts can be useful in terms of providing cursory knowledge related to the experiences of high-achieving and gifted Black students, which, in turn, may help explain why many Black students decline participation in advanced programs and courses. In this article, the authors introduce the influence of hip-hop culture on education and explain how it interacts with Black students' perceptions of "acting White" and "acting Black." This explanation may help stakeholders understand the unique factors influencing the educational decision-making of Black students in the new millennium.