On the 23rd of April, 1616, playwright and poet William Shakespeare died of unknown causes in his home in England, at the age of fifty-two. The next few centuries would bury almost everything about Shakespeare — his exact date of birth, his sexuality, and even his physical appearance remain up to speculation. But among the murky details of his personal life, remain Shakespeare’s writings. The 39 plays and 154 sonnets he left behind have had an incalculable impact upon world culture, and are regarded collectively as one of the greatest bodies of literary work in the history of the English language.

However, even Shakespeare isn’t immune to scrutiny, and throughout the years, scholars and audiences have picked up on strange quirks that seem to sour some of his plays. These so-called ‘Problem Plays’ were first identified by essayist and drama critic Frederick S. Boas as works with a tonal conflict so severe that they couldn’t be categorized as comedies or tragedies. To Boas, there were four Shakespearean Problem Plays; ‘All’s Well That Ends Well,’ ‘Measure for Measure,’ ‘Troilus and Cressida,’ and ‘Hamlet.’

In his 1896 book Shakespeare and his Predecessors, Boas says of the problem plays that “throughout the play[s], we move along dim untrodden paths, and at the close, our feeling is neither simple joy nor pain; we are excited, fascinated, perplexed, for the issues raised preclude a completely satisfactory outcome.”

To Boas, the problem plays were anything but bad (he included ‘Hamlet’ among them as proof of that). They were uncategorizable because they were written during a chrysalis period in Shakespeare’s career when he was switching from lighthearted histories and comedies to more brooding, cynical work tinged with satire and often overflowing with unbridled tragedy. Boas described the transition as “the passage from a sunny charming landscape to a wild mountain district whose highest peaks are shrouded in thick mist.”

The complexity of these plays can intimidate and confuse some audiences and producers, and (with ‘Hamlet’ as the obvious exception) the Problem Plays don’t get nearly as much attention as Shakespeare’s work before or after.

The most well-known of the Problem Plays is ‘Hamlet,’ which tells the story of a Danish Prince tasked with seeking vengeance by the ghost of his murdered father. Hamlet is the most accepted of the Problem Plays for a host of reasons, not the least of which are its easily understandable premise and compelling central character.

Productions of ‘Hamlet’ are predictably Hamlet-centric, and actors lean into the prince’s brooding, questioning nature. Laurence Olivier’s black and white film adaptation in 1948 went as far as to cut the play’s two goofiest characters, Rosencrantz and Guildenstern, from the movie entirely so that they could focus on what Olivier called the “the tragedy of a man who could not make up his mind.”

Traditionally, Hamlet carries both the most prestige and the least mystique of Boas’ Problem Plays and enjoys an exalted position as one of Shakespeare’s most produced works. Boas even considered Hamlet separate from the other Problem Plays, acting as a bridge between them and Shakespeare’s later tragedies.

The second most well-known, ‘All’s Well that Ends Well,’ stars Helena, a woman betrothed to a man named Bertram. Bertram refuses to marry Helena and only does so when he is tricked using a classic Shakspearean ‘bed trick,’ where characters switch out beds to deceive one another. The play is considered both a Problem Play and quite problematic, and the somewhat sudden ending seems to throw out all the ethical questions that the play had posed up until that point for the sake of an unearned happy ending.

‘Measure for Measure’ also features a bed trick, this time on the tyrannical Angelo, who was instituted as the temporary Duke of Vienna and immediately used his power to arrest Claudio for violating the law. Claudio’s sister Isabella attempts to get him out of prison, and Angelo tries to exploit her in exchange for her brother’s freedom. The play is perhaps the most tonally conflicted problem play, and it turns from comedic wordplay to heartfelt soliloquy on a dime.

A loose film adaptation of ‘Measure for Measure’ was released to largely negative reviews in 2019, cementing this play’s legacy as a notoriously difficult one to produce. The Royal Shakespeare Company has produced the play on a semi-regular basis since the 1960s and has taken the play in all sorts of directions in attempts to solve it.

Finally, ‘Troilus and Cressida’ finds a couple torn apart by the waning years of the Trojan War, as the leaders of the opposing armies strategize to destroy one another. The Wikipedia page for the play bluntly notes that audiences are unable to “understand how they are meant to respond to the characters.”

The Royal Shakespeare Company produced a bold version of this play in 2012. The RSC’s own website concedes that “the overall result was a production full of unsettling contradictions, like the play itself.”

Boas died in 1957, and since then the term ‘Problem Play’ has gained a life of its own. The term has now been used to describe almost half of Shakespeare’s plays by one scholar or another. This semantics free-for-all coincided with a general increase in social equity and awareness of offensive stereotypes and harmful themes present in some Shakespeare plays, illuminating a new set of challenges for those seeking to adapt Shakespeare into the 21st century.

The puzzles of Boas’ Problem Plays are time-independent, but modern audiences have a very different idea of what’s acceptable compared to their 17th-century counterparts. This has caused vibrant critical debate about how to interpret some of Shakespeare’s plays in the context of social justice.

‘The Merchant of Venice’ is one such play, and the critical debate surrounding perceived antisemitism is one of the most vibrant in all of Shakespeare, and has extended far beyond the scholarly community and into classrooms around the world. In the play, the Jewish banker Shylock demands a pound of flesh from Venetian businessman Antonio as payment for a debt. Shylock is a divisive character, with some people arguing that he’s nothing more than an antisemitic caricature, and others pointing to his revealing speech in the third act as a plea by Shakespeare for tolerance. Shylock’s “Hath not a Jew eyes?” speech is one of Shakespeare’s most famous. In it, Shylock berates the Christian characters for making him into the villain they feared he was, saying, “The villainy you teach me, I will execute, and it shall go hard but I will better the instruction.”

Anti-semites throughout history used ‘The Merchant of Venice’ to support their points, and Shylock was used in Nazi Germany as a propaganda tool. The play’s divisiveness continues to this day, and debate about Shakespeare’s intent in writing it is some of the most robust in all of Shakespearean scholarship.

Another play that has seen a lively debate spring up around its subject matter is Shakspeare’s earliest work, ‘The Taming of the Shrew.’ In it, the willful Katherine is forced into a relationship with Petruchio, who through various forms of torture turns her into a desirable bride. There is more to this story than what’s on the surface, however, and one reading of the text paints Petruchio and Katherine’s love story as one where man and woman are treated equally.

To attempt to alleviate some of the less palatable aspects of the play, The Public Theater produced an all female-version of ‘The Taming of the Shrew’ in 2016. The production attempted to modernize the play’s depiction of Katherine and Petruchio’s relationship, and it was well-received by critics.

The controversy and debate surrounding this selection of Shakespeare’s plays illustrate why his work has endured. The opportunities that Shakespeare gives actors and directors to interpret his work has allowed even his more problematic works to be continuously reinvented.

Regardless of how you view a particular play of Shakespeare, it’s impossible to deny his global impact upon theater, literature, and poetry. The issue of the Problem Plays and the Problematic Plays barely scratch the surface of what Shakespeare accomplished. Perhaps the greatest lesson that can be drawn from attempts to characterize Shakespeare’s works is that each play is its own puzzle, and that puzzle is missing a good deal of its pieces. It’s the task of directors, actors, and eventually, audience members to fill those pieces in and create a full picture.

The opportunities that Shakespeare gives actors and directors to interpret his work has allowed even his more problematic works to be continuously reinvented.