In a good work, the characters are depicted so accurately that they seem to be real people. At the behest of the author, they face difficulties, face a moral choice, risk their health and even their lives. What if the literary heroes of the past and present, who have suffered a tragic failure, turned to a psychotherapist in time? Would Oedipus Rex's parents have been saved from disaster by parenting advice? Would the story of Romeo and Juliet unfold differently if they were older? Maybe Dracula was not understood by others, and Voldemort was not loved in childhood? Does Fifty Shades of Gray's Christian Gray's erotic fantasies mean he lacks masculinity? The authors of the book, a literary scholar and psychiatrist, subjected some famous characters of fiction to psychological analysis in order to understand what explains their failures, what quirks and problems are universal for everyone, and which are caused by the era.