In partnership with academics from McGill University and community arts partners, a high school in Montreal faced with significant challenges became an "urban arts school," offering music and visual art programs centered in youth culture, as well as integrating arts into several academic subjects. The initiative was inspired by the school's popular extra-curricular activities, which included a Hip Hop literacy club that ran beat making and rap writing workshops. Considering the popularity of these activities, the school decided to offer a music education program focused on musical skills through real-life music making activities that resemble those employed by popular musicians. This article chronicles the development of this music education program from the perspective of the music teacher, including the experience of continual adaptation to the needs and interests of students. The program is one of the first to combine Musical Futures, an approach to music education that promotes the combination of non-formal music teaching, informal music learning, and students' interest in a formal school setting, with Hip Hop Based Music Education, predominantly located in community settings. This case study showed that students benefited from having an open-minded and committed educator with experience in popular musics. The co-teaching by professional Hip Hop artists also supported student progress and engagement by adding authenticity to the music making process. Furthermore, the alignment of the music program with the general school ethos contributed to its success. The paper also highlights the need to balance the development of musical skills with student engagement, and the informal music learning philosophy of Musical Futures with direct instruction associated with formal school settings.