Even though Loncraine’s Richard Ⅲ (1995) and Al Pacino’s Looking for Richard (1996) attempt filming Shakespeare’s Richard Ⅲ they seem completely different works to the modern audience. It’s not only the matter of filming techniques, but that of the representative meanings the directors focus on. The purpose of this paper is to make a comparison analysis of the different political perspectives of Loncraine’s Richard Ⅲ and Alpacino’s Looking for Richard. While Shakespeare’s Richard is a very complicated character, Loncraine’s Richard and Alpacino’s Richard are portrayed rather simple and obvious characters. Shakespeare’s Richard is not a historical king but rather a role-player of villain escaping from history. Loncraine’s Richard and Alpacino’s Richard are the role-players of villain escaping from Shakespearean play. While Loncraine produced a modern film adapting a completely new historical background, Alpacino attempted a documentary film focusing on producing process of Shakespearean drama. If Alpacino plays the role of a kind guide for people who want to know and study Shakespeare, Loncraine and McKellen put new clothes on Shakespeare’s Richard Ⅲ. Loncraine draws out a modern dictator through the character of Richard III evoking Hitler and Mussolini, and presents a satirical message toward dictatorship. Meanwhile Alpacino arouses an effect of epic theater by keeping the audience from being immersed in the film, which make it possible for the audience to enjoy Alpacino’s role-playing and making a film. Furthermore, these two films subtly reveal quite contrasting national feelings of Shakespearean dramas. Loncraine’s Richard Ⅲ, which was made in England, seems to reveal some uncomfortable feelings against America and American film industry. On the contrary, Alpacino’s Looking for Richard well represents the Americans’ dual feelings about Shakespeare. Most Americans don’t have interests in Shakespeare and find it difficult and boring, but they also have some kind of inferiority to English royal tradition. Alpacino seems to attempt overcoming this inferiority and to present his excellence, an American’s excellence.