How does one begin to define a villain? How about a hero? In old Westerns or classic fairy tales, the differences were typically obvious and easily recognizable. The valiant hero dressed in white taking on the ominous bad guy draped in black. Yet, as stories become more modern, distinctions between characters become far less clear. In sixteenth and seventeenth century British Literature, the villain in the role of the protagonist was referred to as a ‘villain-hero.’ Classic examples include Shakespeare’s Richard III and Milton’s Satan. These stories had characters who often proved as interesting, if not more, than the heroes who attempted to stop them. The difference is that in these older tales, the villain generally remained true to their nature, and could never be called a real hero. This changes in the modern era, where villains have risen from their traditional roles to not only take the place of the protagonist, but of the actual hero. From new versions of the fairy tale where the villain pleads to have their side of the story told, to the monster who proves himself capable of showing his once-lost humanity, villains are rising from the shadows into the spotlight. What, exactly, causes a character to become a villain? What part of their history helped to transform them into a character of dark portrayal? Are they villains because of their actions, or the more complex issue of possessing a different set of beliefs from those upheld by the hero or society? This paper will examine these issues by exploring the morals, history and choices of multiple villains, both modern and classical.