Within the mediums of cartoons and comic books/strips, there is an increasing ‘epidemic’ of evil little ‘girls’ who we spy upon as they plot their machinations and execute flawless acts of sadism and maliciousness, often to our collective delight. Writers and illustrators have given these little ‘girls’ license to engage in epic acts of naughtiness. These, at first glance, seemingly harmless little ‘girls’ are agents of malice and deviousness; and, we the audience, seemingly revel in their evil deeds. This chapter is intended as an examination of what inspires authors and illustrators to turn the tables on societal conventions of how little girls should behave; reimaging evil in tiny, cute, little packages down to the ubiquitous frilly dress. Even companies like Sanrio, ™ home of the adorable and non-threatening Hello Kitty and associated characters recently added an ‘evil’ character named Kuromi to their line of critters marketed, largely, to young girls. It would appear there is an increasing desire for little girls to be viewed as more than sweet, innocent and cherubic. Characters such as Mandy from the ‘The Grim Adventures of Billy and Mandy’, and the loveable undead ‘Lenore’ of the ‘Lenore’ comic book series, and many more will be discussed in depth. The diabolical deeds they perform, their victims of choice and their motives will be examined. Psychological profiles, if you will, of these adorable, yet maladapted little munchkins will be provided as well as possible explanations for why we find ourselves so enamoured with them.