This module looks at two of Shakespeare’s darkest comedies (often described as “Problem Plays” and frequently overlooked in Shakespeare studies): Troilus and Cressida and Measure for Measure. Half an adaptation of Chaucer’s tragic romance, and half a reworking of Homer’s Iliad, Shakespeare’s Troilus and Cressida presents both the lovers and the warriors with a mixture of biting satire, comic buffoonery, and genuine pathos. Likely never staged in Shakespeare’s lifetime, this comedy-history-tragedy has puzzled readers since its first appearance in print. In Measure for Measure, a duke’s attempt to clean up his city’s seedy night-life quickly leads to the attempted sexual blackmail of a nun by duke’s chief deputy. In the chaos of bed-swapping and (threatened) head-chopping that follows, the play narrowly avoids outright tragedy, but whether the final ending could be called “happy” has been debated for centuries. These may actually be the strangest two play Shakespeare ever wrote.