Although sport can serve as a valuable mechanism for social change, this does not imply it can single-handedly solve large-scale problems; rather, sport should be utilized with passionate leadership, efficient and innovative program design, and ancillary cultural enrichment activities to achieve optimal results. This research was motivated by developments in some marginalized and at-risk communities where several sport-for-development programs have started to incorporate music to enhance the appeal and impact of sport interventions. The purpose of this study was to evaluate the use of hip-hop and sport by one sport-for-development program to educate and improve the lives of inner-city youth in Harlem. Data were collected by interviewing key stakeholders of the program, including participants, workshop leaders, staff, and upper-level executives along with onsite observations. Results of our investigation highlighted the cultural influence of music and sport within a local demographic and a sport-for-development initiative aimed to appeal to both local at-risk youth and key community stakeholders.