DescriptionThis paper closely examines the heroic Men and villainous enemies of J. R. R. Tolkien’s works, describing in detail the qualities that are required of each. It also draws comparisons between Tolkien’s characters and their medieval romance predecessors, showing that Tolkien borrows heavily from that tradition for inspiration. This paper asks what makes a hero; what makes a villain? But while it highlights the clear cut definitions of what it requires to be considered a hero or villain, it also brings light to the questions regarding the goodness or wickedness associated with these archetypal figures. Here, it is argued that Tolkien did not simply choose the medieval romance genre in order to imitate it; he chose it in order to enhance it. The romance draws a clear line between the hero and his enemies, but rarely develops the characters sufficiently to allow the reader to judge their moral qualities. There is a grey area that the romance shows, where the hero is not always good and the enemy is kept too far out of reach for the reader to examine closely, making it easy to call them bad, but more difficult to actually prove it. Tolkien takes advantage of this grey area and expands on it. He gives detailed histories to many of his villains, as with his heroes. He allows the reader to explore all characters. And he has created a universe where pure evil cannot exist, where evil is only goodness corrupted. He makes all of his characters morally ambiguous at times, which not only makes them more interesting to his readers, but makes them more relatable as well.