This article explores how arts-based pedagogies give insight into the lives and dreams of students who experience detainment and incarceration. This article begins with an overview of imagination as a framework that the authors used to explore student work. They connect the concept of imagination to research on multiliteracies and arts-based pedagogies. The authors invited youth to use art as they reflexively considered the theme of empathy in graphic novel "They Called Us Enemy" by George Takei (2019) and in their own dreams and lived experiences. The authors believe teachers can engage students across learning spaces in art to support students' dreams and ideas to initiate change. This work, although centered in a detention center, has implications for K-12 spaces in which the bodies of marginalized children and youth are over-policed and the opportunities for them to imagine educational spaces as places of hope and liberation are limited. The following question guided this research: How do arts-based pedagogies give insight into the lives and dreams of students who experience incarceration?