The overrepresentation of African American males at risk for academic challenges and special education services, disciplinary actions, dropout rates, and incarceration is an alarming trend in the United States that has been ongoing for over 40 years. Research has shown a correlation exists between a teachers’ cultural competence and a students’ positive academic and behavioral outcomes (Boutte & Hill, 2006; Howard & Terry, 2011; Rychly & Graves, 2012). However, many teachers are inadequately prepared with appropriate content knowledge, experience with culturally relevant practices, and training to address culturally and linguistically diverse students’ learning needs (Sobel et al., 2011). A cultural learning gap between teachers and students, along with, inadequate preparation can limit the choice of effective culturally responsive practices. An educator’s beliefs, attitudes, and expectations can have a major impact on student outcomes. (Ladson-Billings, 2006). Culturally responsive teachers place culture at the center of their teaching philosophy and continuously investigate opportunities to factor culture into all aspects of their teaching to improve the performance of diverse students and close the achievement gap (Bonner et al., 2018). The aim of this study was to understand the perceptions of high school African American males receiving special education services or at risk for academic challenges on teacher responsiveness to cultural diversity. This study used a phenomenological qualitative method to gain insight into the lived experiences of African American males. Limitations, implications for practices and suggestions for future research are discussed.