Le documentariste britannique Nick Broomfield crée une suite à son documentaire de 1992 sur la tueuse en série Aileen Wuornos, une prostituée de grand chemin qui a été condamnée pour avoir tué six hommes en Floride entre 1989 et 1990. En interviewant une Wuornos de plus en plus instable mentalement, Broomfield capture l'esprit déformé d'une meurtrière que l'État de Floride juge saine d'esprit - et donc apte à exécuter. Tout au long du film, Broomfield inclut des images de son témoignage au procès de Wuornos.
Pickett presided over 95 executions in his 15 year career, including the very first by lethal injection. He kept his feelings about his work from his family, instead audiotaping an account of each one. Initially pro-execution, he became an anti-death penalty activist.
The film documents the 1957 San Francisco Actor's Workshop production of the Samuel Beckett's play Waiting For Godot which was performed live before inmates at San Quentin Prison. The film also examines a 1953 performance of Godot by inmates at the Luttringhausen Prison in Germany, providing new scholarship material on those performances.
A lifelong criminal and serial killer, Carl Panzram befriends Henry Lesser, a young jail guard at the Washington DC jail in 1928. After hearing of Panzram's torture, Lesser sends Panzram one dollar and convinces the killer to write his autobiography while secretly supplying him with pencil and paper. Panzram writes over 40,000 words documenting his entire life of incarceration, torture, rape, and murder.