Popular entertainment remains one of the last places where Black history lives on despite the recent political erasure of U.S. Black struggles. The 2021 reboot of The Wonder Years, reframing Black masculinity through the young eyes of main character Dean Williams, rehistoricizes modern notions of Black families in the post-Civil Rights Movement. The purpose of this study is to explore Black masculinity media representations within reboot culture as a means to rehistoricize Black struggle and civil rights. Based on discourse analysis, the authors found the following three discourses: Reimagining Black Excellence, Recontextualizing Black Masculinity, and Revisiting Respectability Politics.