Over the course of theatre's history, villains had stereotypical traits: revenge, greed, and power. Contemporary villains, though, evoke more empathy and sympathy from audiences than classic villains. In an effort to understand the roots of villainous behavior in contemporary characters, this thesis surveys a few notable classic villains to help compare the classic to the contemporary. While holding on to qualities of the classic stereotypes, contemporary playwrights create frequent moments of sympathy and empathy for villains who appeal to audiences' desires to connect, justify, and understand the reasons for their villainies. This thesis investigates despicable yet empathetic villains in three plays: Tony Kushner's Angels in America, Martin McDonagh's The Beauty Queen of Leenane, and Stephen Sondheim and John Weidman's Assassins. An analysis of the playwrights' manipulation of characters and traits, as well as audience expectations, provides a theory on the new villain type and the lessons that can be learned.