In this thesis, I examine the relationship between early modern rhetorical education and Shakespeare’s use of the question in Othello and King Lear, two plays that contain some of the greatest proportions of questions in Shakespeare’s cannon. I argue that even in the plays that seem most skeptical of rhetorical performance, like Othello and King Lear, the protagonists’ development, and developing self-awareness, is heavily dependent upon their use of rhetorical methods. In both plays, rhetoric and early modern methods of teaching it together constitute a force that has the power to harm, even ruin, both its adherents and its detractors. Simultaneously, however, rhetoric and early modern rhetorical education provide indispensable tools for self-examination and self-reflection, tools that benefit conscientious students of rhetoric in a variety of ways. Both of these views are played out through the use (and abuse) of questions in the two plays. I concentrate primarily on how the characters in these plays succeed and fail in employing the kinds of rhetorical practices emphasized in grammar school instruction. For example, in Othello, I consider Othello’s and Iago’s aptitudes for arguing in utramque partem, on both sides of the question, and in Lear, I analyze the characters’ facility in imitatio. The rhetorical successes and failures of the characters reveal much about Shakespeare’s complex relationship with rhetoric. As I hope to show, the characters in Othello and King Lear, like early modern students, either internalize or fail to internalize these principles to their ultimate benefit or detriment. By examining how the characters apply and fail to apply the principles of rhetoric, I aim to illustrate the plays’ complex views of rhetoric as an art that can lead to self-knowledge or to self-destruction—and sometimes to both.