Juxtaposing visuals and stories to represent and interpret data, this visual narrative inquiry uncovers the complicated sociopolitical ramifications conditioning a pedagogy and approach of issues-based avant-garde art in Singapore secondary schools. A brief historical outline of Western avant-garde art connects this genre to the Singapore local art scene and its school art. Stylistic analysis of exemplary artworks from one student art competition illustrates recent trends in students’ artistic interests. An in-situ examination of art curriculum and practice in one secondary school showcases how diluted avant-garde art practice manifested itself in this school. Discussion focuses on (a) the mismatch between avant-garde art and school art practice, (b) neglect of deeper layers of meaning in students’ artistic learning and emphasis on meeting preset exam criteria and standards, and (c) lack of support for experimental teaching methods other than demanding effective teaching results measured by students’ exam performance.