Morality is generally considered as a set of norms and principles that determine the difference between good and bad behaviour as well as concerning the rightness or wrongness of a human act. In literature, moral issues are frequently represented in prose and poetry with the aim to highlight a specific problem, like adultery or blasphemy, and eventually to convey a message to the reader or audience concerning the importance of good conduct. Morality plays, such as the Canterbury tales, written in the late Middle Ages influenced the representation of virtues and conscience of the theatrical performances of the later Elizabethan era. For the purpose of this investigation, a comparison is made between Chaucer’s representations of morality in the Pardoner’s and in the Miller’s tales, and how the same topic is depicted in two Shakespeare’s plays, Macbeth and Measure for Measure.