This article reports a case study on the impacts of an interactive, culturally-sensitive computer-based learning environment on at-risk teenage students' motivation and learning of American history in an alternative school in the United States of America. Hip-hop culture combined with interactive software and digital audio workstations was applied to motivate at-risk teenagers and to promote active and effective learning. Data were collected through interviews, archived multimedia data, learning artifacts, teacher’s notes and reflections. Multiple positive impacts were found on both learners’ motivation and learning outcomes. Implications on practice and research were discussed, together with suggestions for educators, researchers and practitioners.