20 most vindictive characters in movies and shows 

12) Simon Gruber - Die Hard with a Vengeance (1995)

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As the name suggests, Die Hard with a Vengeance features an iconic vindictive villain in the form of Simon Gruber. John McClane killed Hans Gruber and, in the process, made Simon Gruber, his brother, an enemy. Using his intellectual abilities, he makes McClane’s life a living hell. In his mission to seek revenge, he litters bombs in the entire New York City and challenges and humiliates McClane with riddles. He was cruel in a cold, calculative way.

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