This paper aims at exploring the layers of seduction embedded in the two wooing episodes in Richard III-the wooings of Lady Anne and Queen Elizabeth (and her daughter). Both episodes are brimming with psychological, sexual, and political tensions. It is a very difficult task for Richard because of not only his self-proclaimed unattractive outward appearance but also the deep-seated hatred to him in these targeted women. Through a comparative study of two film productions, Laurence Olivier’s Richard III (1955) and Richard Loncraine’s Richard III (1995), this paper aims to focus primarily on how Richard seduces and manipulates his targeted female characters. Also, this paper will explore how both films manipulate audience’s perception and reception through the use of direct address to the audience.