Literary scholars consider the villains of Shakespeare to be among the compelling fictional personas from all time. Psychological conflicts along with ambition and jealousy together with revenge push them toward their villainous behavior. This paper examines if these villains execute their schemes through hysteria or strategical planning. The research evaluates the villainous minds of Iago (Othello) together with Lady Macbeth (Macbeth) and Richard III (Richard III) to reveal the psychological nature of their evil behavior while showing how Shakespeare intertwined insanity with strategic thinking.