Villains have always been a central part of the comic book industry, as the superhero would be unnecessary in the absence of a worthy opponent. Often villains are depicted as single minded, hellbent on destruction, world domination type characters. However, the villains we remember and who reappear to torment the superhero are bursting with personality, charm, and wit– often more than the superhero has his/herself. Alongside these attractive aspects of the villain, madness or insanity is a popular inclusion. No supervillain epitomizes this phenomenon to a greater degree than the Joker, a maniac whose humor is punctuated by grotesque violence and an unnerving obsession with his superhero, Batman. Loki is another popular supervillain whose personality contrasts with his stoic brother and mortal enemy, Thor. Writers for both the Joker and Loki have come out claiming that their characters are gay and bisexual. We will investigate how this aspect creates a more compelling character within their comics, and their impact on comic books as a whole.