As long as incarceration has existed, the desire to escape this fate has existed as well. Over the years, inmates at Sing Sing prison attempted escape many times, in a variety of creative ways. On top of exploring some of the fascinating escape attempts, we will look into the ways that the prison tried to discourage this behavior. Despite any measures taken by the prison, escape attempts continued to happen, showing the desire for agency by prisoners who frequently pushed the boundaries of their incarceration, revealing flaws in the prison system. Escapes also show an interesting relationship between inmates and the public as the media seemed to heroize the cleverest and boldest escapees, despite the crimes they may have committed.