Stories and visuals of Singapore secondary students reflect the ways they negotiate multiple layers of meanings as they experience artistic learning inside and outside the school setting. The photocollage-cum-photoessay representation of one miniportrait features the unique voice of an adolescent wrestling with learning conventional art skills and his schooling in advanced technology. His voice resonates with others regarding balancing personal aspirations with institutional demands and illustrates the failure of prescribed national art curricular objectives to encompass all aspects of adolescents’ artistic learning. A key finding reveals students integrating popular art outside school with their artistic creation, understanding, and appreciation of fine artworks inside the school curriculum. Their experience demonstrates a blend of reality and hyperreality in the contemporary image-saturated world.