Long before art therapists worked in prisons providing clinical services, arts in corrections flourished. This chapter explores how and why art emerged despite—or because of—the limitations imposed on the population. Drawing upon numerous impactful case vignettes, and illustrations of insider art made from found materials, the art completed by those imprisoned in Guantanamo Bay featured in the exhibition “Ode to the Sea,” and complex murals organized and executed over a period of time, this chapter further underscores the natural drive to create inside and the various benefits that art making may offer. What becomes clear is that not only is art making recreationally beneficial for the prison population, but that it has led to one of the most advantageous and therapeutic interventions inside.