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This paper is to compare the two representative villains in Shakespeare, Richard in Richard III and Shylock in The Merchant of Venice, so that we could examine the characteristics of Shakespeare’s villain and further understand how the works become more meaningful though these villains’ attitudes and actions manifested in the play. Shakespeare’s characters defy one-dimensional categorization. While critics are constantly seeking a logical reduction to a single dimension of the characters, Shakespeare forces us to reconcile with the unexpected contradictions in his characters. The poet usually does not allow us to pin down the nature of his characters, and it is therefore always difficult to define a character as a stereotype. In Shakespearean drama, even an obvious stock figure often shows shades of different traits so as to reject a categorical definition. Shylock, for example, is an apparent miser figure, easily recognizable in many Renaissance plays; yet his character shows qualities that prevent us from calling him comfortably the same type of money-grubbers found in Marlowe or Jonson. Richard, a typical egocentric, Machiavellian villain whose behavior is thoroughly wicked and repulsive, nevertheless displays a certain grandeur or self-reliance, commonly found in a tragic hero, so that we create difficulty if we try to narrow down his character simply into a villain. However, the two villains significantly share a predator’s nature and similar appetite as they both struggle to devour what yearn for. And paradoxically, their final destruction provides the seeming victims with nutritions, so they are ultimately devoured by the forces stronger than themselves.