This study is aimed to read Shakespeare's problem comedies, Troilus and Cressida and Measure for Measure into the historical and cultural context of dynamically-changing English Renaissance society at the turn of the sixteenth century. In the historical context of emerging capitalism, growing economic crisis, reformed theology, changing social hierarchy, and increasing sexual control, this study investigates the nature of complicated moral problems that the plays consistently present. The primary argument is that the serious and dark picture of human dilemma is attributed not to Shakespeare's private imagination, but to social, political, economic, and religious crises in early modern England.