This article presents a qualitative analysis of the artistic expression of homeless youths, accompanied by examples of drawings and poetry gathered from youths in New York City and Toronto. The impacts of various forms of marginalization and the meanings youths give their work are examined. These meanings include art as being transformative, self-exploratory, communicative, and a redirection of emotional energy into an artistic medium and expressive process. Parallels are drawn between the art and the marginalization of homeless youths and forms and expressions subsumed under the L'Art Brut and Outsider Art movements.