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The Wicked Witch of the West is one of the most prominent evil female characters in contemporary popular culture. Because of her ubiquity, the Wicked Witch functions as a representation of the evolution of witches from their historical, malevolent context to a popular context more rooted in issues of femininity, subversion, and the nature of good and evil. In discussing the Wicked Witch of the West, this chapter will mainly consider the witches of Gregory Maguire’s Wicked (1996) and Stephen Schwartz and Winnie Holzman’s Wicked: A New Musical (2003) and their development from the original versions found in L. Frank Baum’s The Wonderful Wizard of Oz (1900) and MGM’s The Wizard of Oz (1939). These texts will be analysed from a social perspective, including aspects such as politics, religion, and gender. Each aspect will uncover another facet to the Wicked Witch of the West’s development from a simple, one dimensional villain to a fully-fleshed character. The Wicked Witch’s outward appearance and manner – external indicators of her otherness as a ‘witch’ – relegates her to an exiled position within the literary contexts of her creation. However, this same exile transforms her into a character sympathetic to the audience: the underdog. A disconnect is thus created, for the Wicked Witch’s literary context reads her appearance as corrupt and punishable, which is counter to the internal morality interpreted in the Wicked Witch by the audience. When she descends into wickedness, then, we can read this descent as a representation of the change of society from a dichotomized view of morality to a view much more sympathetic to ambiguity. The Witch, therefore, forces us to question the very nature of good and evil. As Glinda the Good Witch asks in the musical, ‘Are people born wicked, or is wickedness thrust upon them?’