This work attempts to connect two of the most important legal themes: guilt and punishment, analyzing them in general terms, as well as, and specifically, their reflection in world literature, particularly in the work of three writers who excel in this topic, such as Miguel de Cervantes, Fyodor M. Dostoyevsky, and Franz Kafka. The topic of guilt and punishment is studied from both an abstract perspective, as well as in its application to the lives and writings of these three distinguished figures in the history of literature. The first two chapters establish a rich theoretical framework from a variety of perspectives - psychological, religious, juridical. The following chapters take the reader on a fascinating journey through 2,500 years of world literature, from Aeschylus to John Grisham. This back-and-forth between speculative and literary approaches is one of the main strengths of the book. These are just some of the many issues that the author lucidly and insightfully addresses in this captivating new monographic work, which includes an exhaustive bibliography on the subject.