In a good work, characters are portrayed so precisely that they seem like real people. By the will of the author, they face difficulties, are confronted with moral choices, risk their health and even their lives. What if, in time, the literary heroes of the past and present who suffered tragic failure had turned to a psychotherapist? Would parenting counseling have saved the parents of King Oedipus from catastrophe? Would the story of Romeo and Juliet unfold differently if they were older? Would people have understood Dracula, and would Voldemort have been disliked in childhood? Do the erotic fantasies of Christian Grey from “Fifty Shades of Grey” indicate a lack of masculinity? A literary scholar and psychiatrist subjected some famous literary characters to psychological analysis to understand what explains their failures, which quirks and problems are universal for everyone, and which are обусловленны (conditioned) by the era.