Twenty-seven years ago, the documentary "Hoop Dreams" solidified a theory--that the world of athletics was one of the few places where adolescent Black males could find success. By the late 1990s, researchers were framing athletics as the next direction in the Civil Rights Movement. In this article, I argue that the historical framing of Black boys in athletics--as a way up, a way out--is similar to the contemporary framing of Black boys in Hip Hop Based Education (HHBE). Using an ethnographic case example of the Homeboys, a group of adolescent Black males experiencing homelessness, I maintain that HHBE, without critical implementation and reflection, limits the possible selves of Black boys in socially reproductive ways. Unlike "Hoop Dreams," which historically created an incentive to stay invested in formal educational settings, HHBE offers little "possible selves" development for young Black men. This research asserts that if HHBE, and the myriad ways Hip Hop is taken up in formal and informal educational settings is not dually paired with the critical process of institutional actors envisioning "all" the possible selves that black boys can become, then it becomes another hegemonic socially reproductive tool wielded by educators.