Every young girl grows up with fairy tales, Disney princesses, and the ever-so-perfect happily ever after. These animated classics and short stories are viewed and read during a child’s formative years and can have a great impact on how they view themselves in society. Many scholars have discussed the impact the happy endings have on children, but have neglected to discuss the impact of the stereotypical female characters themselves. By analyzing the oppressive nature of female gender roles—specifically in relation to the treatment of the female villain—in the Charles Perrault and Grimm versions of the story of Sleeping Beauty as well as in the 1959 Disney animated film, the conclusion can be made that these stories were used as tools to teach young girls the proper way to dress and act during the time period in which they were produced. Disney’s 2014 live action film Maleficent also acts as a teaching tool, but instead of reinforcing traditional gender roles, I have found that it challenges them, reflecting the views of the new wave of feminism. It allows its viewers to see that the twenty-first century woman is a combination of both traditionally male and female characteristics and can be powerful all on her own. The title character—who was originally used to teach young viewers about the improper actions of women and the consequences that would follow the rejection of gender roles—embodies both male and female traits, creating a vision for the proper representation of women in film beyond just the beautiful damsel in distress or the ugly and evil villainess.