This study is about art, literacy, and adolescents. It addresses a need for research that studies and theorizes arts-based learning for adolescents from sociocultural and critical perspectives, and a need for empirical research on the intersections among the arts, aesthetics, and critical literacy practice. Through participatory inquiry, I explore how arts-based literacy was taken up and understood by students over the course of one school year in two English classes in an arts-based high school. Through sociocultural critical literacy and aesthetic frameworks, I study how art was positioned and engaged in these classes and what this work meant to the teachers and students. Using ethnographic and qualitative methods, I study and theorize this work with and alongside teachers and students. The study analyzes how arts-based learning here meant art as an epistemology, a way of knowing, but it also meant the cultivation of an aesthetic practice, a way of doing, that was nurtured in ongoing ways through invented pedagogical design. In the study, I describe and analyze three domains of this aesthetic practice. Through the positioning of art as story, students came to see their lives as works of art; they learned to resist single stories, cultivate an anti-deterministic stance, and build agentive identities. Students used art as a theoretical instrument for world sense-making; they used art to theorize, inquire, and engage in the social imagination, positioning them as knowledge generators versus passive receivers. Using the relational space of art as a terrain for mapping diverse experience, students engaged in dialogue and came to understand compassion as a mode of critical inquiry and collective action. The teacher and student voices about what engages their hearts and minds, have implications for pedagogy, policy, and research related to the intersections between the arts and adolescent literacy in 21st century learning. The research shows ways that an aesthetic practice that required uncertainty, openness, and relational identity-building enhanced the goals of critical inquiry. Finally, the study makes an argument for the role of aesthetics in critical literacy education, a topic that has been largely absent from mainstream discourses on policy and practice.