This article examines the potential of screen media to disrupt the negative social images of African American youth projected in mainstream culture. Black youth in America have historically been negatively misrepresented and misread within our society through mass-mediated images on television and film. The “negative social imagery” of African American youth across media continues to contribute to their marginalization and plight within society. Recent scholarship suggests that problematic values and behaviors of inner-city Black youth—violence, hypermasculinity, misogyny, drug addiction, educational failure, unemployment—is attributed to their near-total immersion in the mainstream mass media. This supports the notion of “they will be what they see.” But what if we offer them something different? Something more positive? Something within a Black cultural history rooted in a strong tradition and legacy. Drawing from such social media platforms as YouTube and Vimeo, in conjunction with ethnographic fieldwork and music analysis, this study investigates the potentially positive outcomes of presenting an alternative representation of Black youth through a jazz tradition that extends back to the great Buddy Bolden. Recreating the image of African American youth requires a multidimensional paradigmatic shift, disrupting mythological narratives that invoke further harm and misconceptions. To successfully redirect this pathology, I draw on Tyrone Howard, Terry Flennaugh, and Clarence Terry's (2012) lead and incorporate the views, ideas, and perspectives of the Black males themselves in re-creating their own mediated images. This project offers a model suggesting a more profound and critical approach to narratives, histories, and ethnographies of African American youth across screen media.