
Seriously, Portia, why screw Shylock over everything. The worst thing he’s done is asking for pound of Antonio’s flesh because he treats him like shit and gets away with it. For God’s sake, this Venetian Anti-Semitism is getting of hand.
Finally, we get to Shakespeare’s problem plays. Now while some of these are considered either comedy or tragedy, they don’t fall into either. Nor do they seem to have completely happy endings. Or barely believable ones. Nevertheless, they tend to be characterized by their ambiguous tone which shifts violently between dark, psychological drama and more straightforward comic material. And in these plays, the protagonist often faces a situation put forward by the author as a representative of an instance pertaining to a contemporary social problem. Or whatever is interpreted as such like in The Merchant of Venice. However, the term can refer to the play’s subject matter or the classification “problems” with the plays themselves. These ones usually fit the bills in most cases.
34. All’s Well That Ends Well

Helena: “Great floods have flown/From simple sources; and great seas have dried,/When miracles have by the greatest been denied./Oft expectation fails, and most oft there/Where most it promises.” – Act II, Scene 1
Genre: Problem Play, Late Romance, Comedy
Published: 1604 or 1605
Plot: Poor servant girl Helena has an unrequited crush on the countess’s son, Bertram who leaves to become a courtier to the ailing French King. Well, she basically stalks Bertram and promises that she can save the king since she learned some medicinal skills from her late physician father. The king is skeptical but gives her a try but reminds her that she’d be executed if she fails. But if she succeeds, she can marry any guy in his entourage. Helena cures him and the king lets her take her pick. As expected, she chooses Bertram who rejects her because she has no wealth or social status. The king will have none of it so he gives Bertram no choice. But after the ceremony, Bertram escapes to fight in Italy and sends a taunting letter to Helena bragging how he’s left her and saying that he won’t have her as his wife unless she wears his family ring and has his baby, expecting that neither is going to happen since he has no plans returning to France. Distraught but undeterred, Helena follows him all the way to Florence where she finds out that he’s set his sights on a girl named Diana who’d rather have him off her back. So Diana helps Helena by convincing Bertram to give up his family ring and letting him sleep with her in her room with the lights off. That night, Helena sneaks in Diana’s bedroom and sleeps with Bertram instead. After that, Helena returns to France where she fakes her own death with the countess’s help, prompting Bertram to return home. Thinking he’s free of her, Bertram tries to marry someone else but Diana shows up and ruins it for him. Once everyone shows up, Helena reveals herself showing that she’s not dead, is wearing Bertram’s family ring, and is pregnant with his child. Bertram is impressed with all she’s done for him and swears his love to her.
Plot Origin: Based on a tale in Boccaccio’s The Decameron. Shakespeare might’ve read an English translation of the story in William Painter’s Palace of Pleasure.
Who Falls In Love: Helena loves Bertram who’s an utter tool while he has a thing for Diana who reasonably suspects he wants to get in her pants. Yet, by the end, Bertram appears to reciprocate but he may not have been sincere since he’s spent most of the play as a complete prick who hates her guts and only seems to change in just one line.
Who Dies: Nobody.
Reputation: This isn’t one of the best know Shakespearean plays since it wasn’t very popular in his lifetime. A lot of performances tend to play down Bertram’s assholery or portray him as emotionally immature. However, while Helena’s love for the unlovable Bertram is hard to explain on page, this could be corrected on stage by having him cast by a hot actor. Jon Hamm comes to mind for me.
35. Measure for Measure

Mariana: “I cry you mercy, sir; and well could wish/You had not found me here so musical:/Let me excuse me, and believe me so,/My mirth it much displeased, but pleased my woe.” – Act IV, Scene 1
Genre: Comedy, Problem Play
Published: 1603 or 1604
Plot: Duke Vincentio is concerned that Vienna’s anti-premarital sex laws aren’t being observed in the city (for obvious reasons). So he decides to leave Vienna and leaves his assistant Angelo in charge in the meantime (when in reality, he’s just going to dress up as a friar and live among the common folks so he’d know how to better serve them as well as see Angelo handle things if he really did go away). At first, Angelo proves to be a stricter ruler and enforces the anti-premarital sex laws ruthlessly. But he allows power to go to his head as seen by him sentencing Claudio to execution for knocking up his fiancée Juliet just to serve as an example to men who can’t keep it in their pants. And Claudio is perfectly willing to marry Juliet, too. This leads to his sister, a novice nun named Isabella to visit him and plead her case with Angelo. Angelo agrees to spare Claudio’s life on the condition that Isabella sleep with him. Isabella refuses because she doesn’t want to lose her virginity and knows that no one would believe her if she accuses him of rape (which it technically is). So she just tells Claudio to get his affairs in order. Fortunately, the Duke has a scheme so Isabella won’t have to decide. Because Angelo had once agreed to marry a woman named Marianna but he reneged on her promise when her dowry was lost at sea. The Duke suggests that Marianna disguise herself as Isabella and sleep with Angelo instead. Nevertheless, after the sex, Angelo goes back on his word and orders Claudio’s execution anyway because he doesn’t want to be exposed as the hypocrite he is. The Duke then proposes that instead of Claudio’s head, they’ll just send the head of an actual guilty prisoner. Unfortunately, the only criminal up for execution is too drunk to be killed so they send the head of a pirate who died of a fever. After that, the Duke decides he’s played dress up for far too long and resumes his role as Vienna’s ruler. Isabella and Marianna complain that Angelo wronged them but he plays dumb. Angelo blames everything on the mysterious friar who’s been hanging around and he’s backed by a Lucio, a local pimp. The Duke leaves and disguises himself as a friar as Lucio accuses him of various crimes. So the Duke reveals himself to set everything in order. He forces Angelo to marry Marianna and condemns him to death. But pardons him when Marianna and Isabella plead to spare him. He then brings Claudio out alive and reunites him with Juliet. He condemns Lucio into marrying a whore who had his child but pardons his life. And finally, he proposes marriage to Isabella but the play ends before she can give an answer.
Plot Origin: Based on original is “The Story of Epitia”, a story from Cinthio’s Hecatommithi, first published in 1565 and George Whetstone’s drama Promos and Cassandra. Still, why the characters have Italian names in a city whose main language is German I have no idea. Nevertheless, to have Claudio jailed and sentenced to death for knocking up a woman he’s perfectly willing to marry would’ve been seen as ridiculously cruel, even by the standards of Shakespeare’s time. In fact, even in Shakespeare’s time, a woman being pregnant at her wedding was a fairly common thing.
Who Falls In Love: Claudio with Juliet to the point where they can’t control their hormones, Angelo with Isabella who doesn’t care for him much and it’s more like lust, Duke Vincentio with Isabella though we’re not sure about her, and Marianna with Angelo. Lucio is condemned to marry a prostitute who had his baby.
Who Dies: A pirate dies of a fever.
Reputation: This isn’t one of Shakespeare’s best known plays and one I wouldn’t recommend as appropriate for the whole family (even though in Shakespeare’s day, parents didn’t give a shit what was proper viewing for children anyway). Though general consensus has Isabella marrying the Duke, whether she does is entirely up to the director. And we’re probably better off not knowing anyway. Still, this is more of a dramedy than a comedy and it’s well known for its frankness on sex. But it has a happy ending. Made into a musical.
36. The Merchant of Venice

Shylock: “And what’s his reason? I am a Jew!
Hath not a Jew eyes? Hath not a Jew hands, organs, dimensions, senses, affections, passions; fed with the same food, hurt with the same weapons, subject to the same diseases, healed by the same means, warmed and cooled by the same winter and summer as a Christian is? If you prick us, do we not bleed? If you tickle us, do we not laugh? If you poison us, do we not die? And if you wrong us, shall we not revenge?” – Act III, Scene 1
Genre: Comedy, Problem Play
Published: 1596-1598
Plot: Noble Bassanio is broke and seeks the hand of Lady Portia because she’s an heiress with wads of cash. So he approaches the merchant Antonio to borrow money because the guy’s often bailed him out in the past. But Antonio’s merchandise is out to sea and doesn’t have much money at hand even though he’s willing to give Bassanio any dough he can get. So Bassanio finds Shylock who hates Antonio, partly for being a Christian but mostly for Antonio insulting him and spitting on him for being a usurer. Shylock agrees to the loan and won’t charge interest this time. However, if Bassanio doesn’t pay back the loan, he gets a pound of Antonio’s flesh. But since Antonio’s ship will be in a full month before the money is due, Bassanio doesn’t worry and signs the bond. Bassanio goes to see Portia but since half the men in Europe want to marry her so he has to wait in line. However, her dad left a will saying that any guy wanting to marry her has to select among 3 caskets, one silver, one gold, and one lead. The princes of Morocco and Aragon choose the first 2 and go home unhappy. Bassanio chooses the lead one which was correct so he gets the girl. Later Antonio hears that his ship has gone down in a storm and is in serious trouble for he can’t give Bassanio the money to pay back the loan. And to make matters worse, Shylock’s daughter Jessica has eloped with one of Bassanio’s friends Lorenzo who’s a Christian and has taken most of Shylock’s money with her. So Shylock is even in a worse mood than previously so he has Antonio arrested and brought to court to claim a pound of his flesh. Portia and Bassanio hear about Antonio’s plight and Portia offers to pay 3 times the amount that’s owed while disguising herself as a man. Shylock refuses because his hatred toward Antonio is personal. While Shylock does receive a pardon, he loses practically everything to his daughter who betrayed him and is forced to convert to Christianity.
Plot Origin: Based on the 14th century tale Il Pecorone by Giovanni Fiorentino, which was published in Milan in 1558 and The Orator by Alexandre Sylvane, published in translation in 1596, and “Gesta Romanorum”, from the 13th century.
Who Falls In Love: Bassanio and Portia, Jessica and Lorenzo, and Gratiano and Nerissa. Some speculate that Antonio is in love with Bassanio.
Who Dies: No one on stage. Though some adaptations have Shylock kill himself.
Reputation: This play has had a very interesting reception over the years and that’s mostly thanks to Shylock. And it’s also among Shakespeare’s most controversial, also thanks to Shylock. In fact, this play should’ve been called “The Angry Jewish Moneylender of Venice Everyone Treats Like Shit” because Shylock is usually the most coveted role and the character in the play everyone remembers. And there’s a lot of debate among scholars on whether Shylock is supposed to be an Anti-Semitic stereotype or truly sympathetic character who suffers a tragic fate. Sure Shylock is kind of an asshole and asking for a pound of a guy’s flesh is excessive, but in many ways you can totally understand where he’s coming from since Antonio treats him like shit and gets away with it. In the end, Shylock loses his daughter, his fortune, his property, and his religion. And despite wanting to kill Antonio, all the other characters treat him far worse than he treats them. As for Antonio while he might be a complete jerk, you have to admire how he’d do almost anything he could for Bassanio. Some scholars have speculated whether Antonio sees Bassanio like a son or is gay and has an unrequited love for him. Made into a 2004 movie starring Al Pacino as Shylock and Jeremy Irons as Antonio.
37. Timon of Athens

Timon: “Why, I was writing of my epitaph;
it will be seen to-morrow: my long sickness/Of health and living now begins to mend,/And nothing brings me all things. Go, live still;/Be Alcibiades your plague, you his,/And last so long enough!” – Act V, Scene 1
Genre: Tragedy, Problem Play
Published: 1605-1606
Plot: Timon is a beloved citizen of Athens known for his generosity. Unfortunately, he surrounds himself with flattering cronies, rewarding their flattery with lavish gifts. But they care about is when they’ll get their next payout. He holds a massive feast where he invites all his friends, many of whom he’s helped with personal problems by him throwing money at them. The only one in attendance who doesn’t suck up to him is Apemantus who’s only there to snark at him and his flatterers. Then Timon’s steward Flavius tells him he’s deeply in debt and can’t even sell his lands to recover. Timon sends servants to 3 of his closest friends by they shoot each one down. Timon is heartbroken but decides to throw another feast. This time, Timon gives his former friends an elaborate “fuck you,” serves them a “soup” of warm water, and chases them all out of the house with stones. Timon is exiled from Athens and goes to live in a cave outside its walls spending most of his time wishing plagues and disaster onto the city. He runs into Alcibiades who tells him that he’s going to sack and ruin Athens. Timon encourages him and gives him the gold he found to fuel the campaign. Alcaibiades is reluctant to be so vicious but says he’ll avenge both of them. Timon’s old friends soon hear he’s suddenly wealthy again and go to him, hoping to enjoy his generosity. But instead they’re met with disdain and vicious insults. Apemantus to deliver an “I told you so,” and the two have a comical battle of wits before Timon chases him away with stones. And the only person Timon doesn’t hate is his old servant Flavius who visits him but doesn’t ask for money. Timon gives him the rest of his gold and tells him never to be generous to anyone. Alchibiades attacks Athens but the authorities convince him not to. He agrees but receives word that Timon is dead.
Plot Origin: We’re not sure what Shakespeare based this play on.
Who Falls In Love: No one for there are no women in the cast.
Who Dies: Timon but we don’t know how. Possibly suicide.
Reputation: One of Shakespeare’s most difficult and obscure plays as well as often viewed as his “least liked.” However, Herman Melville was a noted fan. Performances of this play had been dominated by adaptations from the Restoration until well into the 20th century. It’s about to have its first film adaptation coming out at the end of this year. Does not have a sequel called Pumba of Athens. Sorry Lion King fans but this isn’t a Hakuna Matata play. Really it’s not.
38. Troilus and Cressida

Troilus: “The Greeks are strong and skilful to their strength,/Fierce to their skill and to their fierceness valiant;/But I am weaker than a woman’s tear, /Tamer than sleep, fonder than ignorance,/Less valiant than the virgin in the nigh/ And skilless as unpracticed infancy. ” – Act I, Scene 1
Genre: Problem Play, Tragedy
Published: 1602
Plot: Troilus is a brave Trojan warrior falls desperately in love with Cressida. She reciprocates but plays hard to get. So Troilus uses Cressida’s scatterbrained uncle Pandarus as a go-between and spends most of the play singing Troilus’s praises and making bawdy jokes. Eventually they have sex and profess their undying love. But Cressida’s father who defected to the Greeks, exchanges her for a Trojan soldier so they get separated. Trolius asks her to be faithful and gives her a sleeve to remember him by. Yet, he can bear to be apart from her so when everyone gathers in a duel, he decides to visit her. Unfortunately, he finds out that Diomedes seduces (or rapes) her. Pissed off, Troilus kills some Greeks and yells at Pandarus who wonders what he did wrong. Meanwhile, Agamemnon is upset that Achilles won’t get out of his tent to fight the Trojans. Ulysses and Nestor concoct a plan to get Achilles back into battle by sending Ajax to duel Hector instead, hoping that this will infuriate the Greek champion into fighting. And for good measure, Ajax boasts and beats up a smart ass servant. However, the due falls through though Achilles is back on the battlefield. He and Hector duel the next day yet Hector drives him off. But Achilles later catches him unarmed and orders his men to kill him.
Plot Origin: Based on Homer’s Iliad and Chaucer’s tale Troilus and Criseyde.
Who Falls In Love: Troilus with Cressida but it doesn’t last. Then there’s Cressida having sex with Diomedes (but I highly doubt this is consensual). Also, Hector and Andromache (but he dies) as well as Achilles and Patrolcus (depending on your interpretation).
Who Dies: Hector gets killed by Achilles (though this is keeping true with the source material).
Reputation: Readers and theater goers don’t know how to react to this play since neither of the main characters die as so much as breakup. Also Troilus is kind of a dick asking Cressida to be faithful to him when she’s taken as a POW as if she’s totally in control of the situation (sorry, she’s not). And though he has every right to be pissed when she’s seduced by Diomedes, he acts like it’s her fault despite that female POWS are especially vulnerable to being raped. This is especially true in the Trojan War when the Greeks took every Trojan woman as a sex slave after Troy’s fall. Also, he never really promises her to keep it in his pants or rescue her. Still, this play has never been popular and hasn’t had performances between 1734 and 1898. John Dryden had a version in which Cressida stays loyal to her Troilus throughout which I think is even worse. And it wasn’t staged in its original form until the early 20th century mostly thanks to WWI owing to its cynical depiction of immorality and disillusionment.