This chapter undertakes a keyword analysis of seven Shakespearean characters: Titus, Tamora, Aaron, Lear, Edmund, Macbeth and Lady Macbeth. The chapter discusses how, once contextualised, these keywords provide useful insights into their feelings/thoughts towards others, events, motivations to act, etc. In terms of findings, only Aaron denotes his "villainy" directly. Tamora, in contrast, draws upon a keyword that is denotatively positive; in context, though, "sweet" reveals her womanly wiles. "Weep", for Lear, and "legitimate" and "base", for Edmund, problematize their status as (one-dimensional) villains. Macbeth and Lady Macbeth draw upon grammatical keywords, "if " and "would" in ways that signal something about their (deteriorating) emotional and social positions as much as their villainous intentions.