As a result of the groundbreaking success of his debut film Boyz N the Hood (1991), filmmaker John Singleton gained worldwide acclaim, the respect of major film industry figures and became the topic of both scholarly and popular culture film conversations. He also made history, becoming the youngest and the first African-American to be nominated for the Academy Award for excellence in directing. However, the lukewarm critical reception for his sophomore release Poetic Justice (1993) countered the promise many felt he had shown earlier and initiated a lack of interest in Singleton's subsequent films, rendering him almost obsolete from any future cinematic analysis. This dissertation seeks to resurrect the discussion of John Singleton as a substantial contributor to the world of cinema by bringing attention to the voice that he has given young African-American men and women in the works that comprise what he calls his "hood trilogy," which includes the aforementioned films and Baby Boy (2001). Specifically, the dissertation addresses this topic by examining how Singleton's own discussion of black masculinity via film is an extension of the same conversation about maleness began by writers Richard Wright and Ralph Ellison, how the South Central Los Angeles environment has had a tremendous effect on the behaviors and attitudes of the young people that populate the area, the influence of hip hop culture on gender dynamics, and the strain often placed on black male/female relationships in urban settings.;The methodological approach of the dissertation combines film, literature, music, and cultural and sociological studies in the effort to locate Singleton and these films as meaningful components in the investigation of film, popular culture and African-American history and culture. In analyzing these films that, as a result of their subject matter and setting, find the filmmaker at his most assured both narratively and cinematically, the intent of the dissertation is to confirm the potential that Singleton revealed in his debut and also bring awareness to the significant effect his work has on African-American youth culture at large.