Black boys generally have the most disparate outcomes (i.e. exclusionary punishment and office referrals) in regard to discipline in schools, which necessitates the need for interventions to help alleviate this issue. As such, the purpose of this study was to examine the effectiveness of a video self-modeling (VSM) intervention on students' challenging behaviors in an urban school setting. Utilizing an A-B-A-B withdrawal design, four Black boys in elementary school participated in the intervention. Results of visual analysis and Tau-U (Zion -1, p = 0.0018; DeAndre -1, p = 0.0027; and Malik = -0.6775, p = 0.0343) indicated significant and positive effects of VSM in relation to students' behavior. Furthermore, teachers found the intervention to be acceptable based on the Intervention Rating Profile-15 (IRP-15). Future research and implications for the use of video self-modeling in urban schools are discussed.