African-American males are conspicuously underrepresented on the nation’s college and university campuses, and in many highly paid and socially important professions. Prior research into this phenomenon has focused on individual- and environmental- level deficits related to college preparation, offered few interventions to increase black male success, and typically represents black males as a monolithic group whose under representation is a result of its own particular characteristics. Few researchers have interrogated the cultural triumvirate of media, education, and law enforcement and the seamless way in which these domains scaffold representations of black males as second-class citizens, who are inauspicious academically, and ultimately represent social threat. To explore the implications of these cultural representations and processes on individual’s college going aspirations and trajectories, this phenomenological qualitative study examined the meaning making of 20 college going African-American males to examine how they perceive media representations of blackness and college going. We ask whether these portrayals promote, discourage or are silent about the unique gauntlet black males must negotiate to and through college. While the lack of preparation and the financial ways and means of college are concerns for all students, black males must additionally negotiate structured racism, in the form of deficit perceptions, infrequent recommendation for advanced placement, and differential experiences with school discipline and law enforcement. The study uses an ecological framework, in which the totality of student experiences is explored in the environments where they are encountered. The focus is on what strategies have worked rather than adding to the already-significant body of deficit literature. The study probed black male college going decisions and how those decisions were shaped, altered, or supported by perceptions students may have developed from mass media representations. Media act as a kind of surrogate for personal contact, which individuals use to assess and judge their social worlds. This powerful and ubiquitous curriculum, although informal, has implications for how others view black males, as well as how they may view themselves and their opportunities.