• The Oresteia (#1-3) - Aeschylus, per. 458 BCE/pub. ???
    • The Trojan war may be over, but Agamemnon's troubles are only beginning. This riveting trilogy of plays (Agamemnon, The Libation Bearers, The Eumenides) by Aeschylus chronicles the trials and tribulations of the King of Mycene and his family upon his return from the events of The Illiad. A sobering meditation on the nature of justice and vengeance, The Orestia has lost none of its potency. 
  • The Knight of the Burning Pestle - Francis Beaumont, per. 1607/pub. 1613
    • Oh, you thought self-aware fiction was a 20th-century invention? THINK AGAIN. The characters in Beaumont's delightful 17th-century meta-comedy are attempting to stage a play, but a couple of snippy hecklers are constantly dictating what they would like to see—even going so far as to demand that their apprentice have a role in the production. The performers bend to the will of their critics. The Knight of the Burning Pestle has somehow become exponentially more relevant over the years, slyly commenting on the tumultuous relationship between artist and audience that has defined, in particular, the televisual landscape (also: all artistic media). It's fun, funny, and has something to say. 
  • Angels in America: A Gay Fantasia on National Themes - Tony Kushner, per. 1991/pub. 1993
    • Kushner's genderbent, metafictional text—probably the final masterpiece of theatre to be released in the 20th century—about the AIDS crisis, Mormonism, the Cold War, and the push for gay rights in late-80s/early-90s America is a messy, confounding work in two parts: Millennium Approaches and Perestroika. But that mess is rich with metaphor and symbolism that speaks strongly to the profound role that art plays in the movement for equality and acceptance, and it is difficult to overstate the profound role that Angels in America itself had in the movement for gay rights over the subsequent decades. Many pieces of theatre are artistically important, but few are as culturally important as this. 
  • Doctor Faustus - Christopher Marlowe, per. 1592/pub. 1604 (A text) and 1616 (B text)
    • Marlowe's dramatization of the German legend—the chronicle of man who attempts to summon a devil and signs away his soul in exchange for power—is deliriously twisted in its small scope, leveraging the pettiness and resignation of Faustus as juxtaposition against the momentous stakes to which he has willingly blinded himself. There are two versions of the text available; they contain some subtle and some significant differences which greatly alter the tone of the play and the weight of certain themes. The two versions are included side-by-side in many editions, and they are both worth reading. 
  • The Changeling - Thomas Middleton & William Rowley, per. 1622/pub. 1653
    • There are few storytellers who know how to execute a downward spiral like the early modern playwrights, and The Changeling is one of the best; like Macbeth or Othello, you want nothing more than to throw yourself in the midst of the characters and tell them to stop it, stop it before everything goes to hell. But go to hell it does. The characters in question here are Beatrice and De Flores, who are hopelessly caught in one another's orbits and drag everyone down around them as they descend into madness and bloodshed. The desperate struggle against the social hierarchy feels especially relevant.
  • The Crucible - Arthur Miller, per. 1953/pub. 1953
    • Reframing McCarthyism through the lens of the Salem witch trials, few political texts have juxtaposed the historical and the contemporary to such effortless and devastating effect. Even beyond its pointed criticism of times past, though, The Crucible remains an extremely compelling drama about the insidious nature of paranoia and groupthink and their combined ability to destroy innocent lives. 
  • Hamlet - William Shakespeare, per. ???/pub. 1603
    • Do I really need to explain why you should read Hamlet? You've either already read it, seen it, or know full well how important it is and are feeling guilty for never actually picking up a copy. But Hamlet is one of those texts that actually holds up to its reputation: Shakepeare's wordplay is rarely better, and there's a nigh-inexhaustible richness to both its personal and political themes, namely the insidiousness of madness, the cyclical nature of vengeance, and one's obligation to family and country. Seriously. It's Hamlet. It doesn't matter if you're a serious reader or a casual one, you need to read it. 
  • Henry VI, Pt. 1 - William Shakespeare, per. 1592/pub. 1623
    • Henry VI, Pt. 1 isn't exactly one of my favorite Shakespeare plays—the writing is uncharacteristically flat, perhaps due to inexperience or collaboration with another playwright, and it lacks the scope and thrills of Henry VI, Pt. 2 and 3 (although it does have Joan of Arc, so that's a plus)—but it's still Shakespeare,  and it's still an important representation of pivotal events in English history. This is the inception of the Wars of the Roses (the inspiration for A Song of Ice and Fire), the conflict which will span one of Shakespeare's great historical chronicles: the first tetralogy (Henry VI, Pt. 123 + Richard III). 
  • Henry VI, Pt. 2 - William Shakespeare, per. 1592/pub. 1623
    • Much grander in its ambitions than Henry VI, Pt. 1 (and much more sharply written), Pt. 2 amps up the violence considerably as the political drama surrounding the Wars of the Roses escalates into bloodshed. Henry VI, Pt. 2 probably isn't the first play your average reader will think about when they think about Shakespeare—after all, it's the second entry in a series about a king who has hardly entered the popular consciousness—but it's as visceral and as thrilling as his most famous tragedies. 
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  • Henry VI, Pt. 3 - William Shakespeare, per. 1592/pub. 1623
    • Although it does not conclude Shakespeare's first tetralogy (the story continues in Richard III), Henry VI, Pt. 3 ends the Henry VI sequence with...even more violence. A lot of violence. Henry VI himself is less effectual than ever, and Queen Margaret gloriously surges in to fill the vacuum of power and destroy her enemies; Richard Plantagenet, meanwhile, uses the ensuing bloodbath as an opportunity to slaughter his way to power. Henry VI, Pt. 3 is a dense play, at once both exciting and sickening in its abundant portrayals of violence, and it puts all the pieces in place for the bombastic Richard III
  • Julius Caesar - William Shakespeare, per. 1599/pub. 1623
    • Arguably even more important to pop culture than the actual events of Caesar's life and death, Julius Caesar is not about its titular character so much as the people who surround him and the ways in which they attempt to navigate the dangerous terrain around a person with immense power and the even more dangerous landscape around the vacuum that such a person leaves behind. Even Hamlet fails to capture with such subtlty the disparity between good intentions and bad outcomes. 
  • Macbeth (aka The Scottish Play) - William Shakespeare, per. 1606/pub. 1623
    • Macbeth, as savage as it short (it's the briefest of Shakespeare's tragedies), is a deeply sad play that chronicles both power and premonition and their ability to distort the mind beyond rational thought. Rarely have the paranoia of rulership and the guilt of getting there been illuminated with such painful and sorrowful dialogue, but it's hard not to be riveted by the spiraling drama of Macbeth and his infamous wife. This is not only one of Shakespeare's most iconic plays, but also one of his best. (And in case you needed any more convincing, Macbeth's climactic moment pivots on a devious bit of wordplay—who else but Shakespeare could pull that off with slipping into unintentional hilarity?) 
  • The Merchant of Venice - William Shakespeare, per. pre-1600/pub. 1600
    • I don't think anything written by the Bard has exponentially increased in relevance over the years quite like The Merchant of Venice. Its portrayal of Jewish characters is complicated and challenging, especially post-Holocaust, and it's a testament to Shakepeare's talent that it remains so difficult to decipher how exactly we, as the audience, should feel about Shylock. Like Milton's Satan, we struggle to pick apart the impossible paradox that he presents: how can the most evil character in the story also be the most sympathetic? Is he really that good at playing us? Or are we just on the wrong side? 
  • A Midsummer Night's Dream - William Shakespeare, per. pre-1600/pub. 1600
    • A hallucinatory romance where the human world collides with the magical world of faeries, A Midsummer Night's Dream follows multiple couples whose true feelings for one another are muddled by spells and potions; a comedy of errors results. Uproariously funny and drawing heavily upon mythology—Theseus is a major character, and the famous play-within-a-play features Pyramus and Thisbe—this is one of Shakespeare's most popular and enduring texts. It's well worth reading. 
  • Much Ado About NothingWilliam Shakespeare, per. pre-1600/pub. 1600
    • Much Ado About Nothing—the title itself—is a three-pronged play on words, referencing the vapidity of the conflict in the text, the use of notes amongst the characters ("nothing"/"noting"), and "nothing" as a euphemism for vaginas. This multi-faceted language could not be more fitting: Much Ado About Nothing is one of Shakespeare's wittiest plays, featuring dialogue so tangled with puns and double- and triple-entendres that you can read it over and over again and still discover fresh jokes lying in wait. It's a sharp, snappy work that is as richly rewarding as any of the Bard's devastating tragedies. 
  • OthelloWilliam Shakespeare, per. 1604/pub. 1622
    • Hamlet gets all the credit, but Othello is peak Shakespeare; Paradise Lost is the only thing written in the English language that I would dare to say is better, and even that is with a great deal of hesitation. Deftly intertwining the discomfort of race relations with issues of fidelity and paranoia, facilitated by one of Shakespeare's most iconic villains, Othello escalates like clockwork and culminates in a climax that speaks to a theme which has driven literature since time immemorial: the relationship between sex and death. This is Shakespeare at his best. This is literature at its best. Othello is a masterpiece. 
  • Richard IIIWilliam Shakespeare, per. 1633/pub. 1597
    • Shakespeare's first tetralogy concludes in one of his densest and most devious plays—one of his most famous, too, and rightfully so. The machinations of Richard III can be challenging to pick apart if you are not familiar with the contextual history or are not prepared to study the text in detail, but this is a deeply rewarding work for the careful reader; Richard is a character who is as fascinating as he is horrifying to watch, and his long fall leaves behind a bloody thematic web of disability, power, and guilt that one could spend a lifetime untangling. Shakespeare is rarely more essential than Richard III
  • Romeo and JulietWilliam Shakespeare, per. pre-1597/pub. 1599 (Q2)
    • Even if you somehow haven't read Romeo and Juliet (or seen it performed), you probably still don't need me to tell you why you should. Shakespeare's dialogue sings in this play—the conversation leading up to Romeo and Juliet's first kiss famously forms a sonnet, a unnecessary detail which slays me every time—and there's a heavy dose of truly filthy humor to soften the romance. If nothing else, you should read Romeo and Juliet to clear up the elements that have been distorted by pop culture. 
  • Titus Andronicus - William Shakespeare, per. 1594/pub. 1594
    • Titus Andronicus was, for a long time, looked down upon in the Shakespeare canon; it's the Bard's equivalent of a slasher flick, a gloriously hyperbolic bloodbath that veers dangerously close to unintentional comedy. But the heightened emotions provide Shakespeare with ample opportunity to show off his most elegant poetry, and there's as much richness in the themes and symbolism as anything in Hamlet or OthelloTitus Andronicus actually has much in common with the latter masterpiece, confronting similar questions of race and revenge and sexuality. It's worth reading.
  • The Winter's TaleWilliam Shakespeare, per. 1611/pub. 1623
    • This strange, magical tale has a texture entirely its own: featuring unexpected leaps in space and time, an actual appearance from Time, a dose of magical realism, and the most famous stage direction in all of Shakespeare, it's an unforgettable piece that defines convention. Winter's Tale is sometimes considered to be one of Shakespeare's so-called "problem plays" due to tonal inconsistencies and difficulties in classification (comedy it may be in technicality, but there is an element of true tragedy), but that's precisely why it's so fascinating—it's a discomforting work that can be hard to pin down. 
  • Antigone - Sophocles, per. c. 441 BCE, pub. ???
    • Antigone is something of a battle of wills between its titular character and Creon, a tyrannical ruler who believes that Antigone's brother, who (supposedly) dishonored himself in civil war, should not be given a proper burial. Antigone herself is almost a Rorschach-esque character, a woman who will break before she bends, who is intent on standing up against Creon no matter the cost to herself and those she cares about. It's a breathless and challenging play that deals with questions of family, honor, and civil disobedience; Antigone is a painful read, but it remains an extremely important one. 
  • Harry Potter and the Cursed Child (Harry Potter #8) - Jack Thorne, per. 2016/pub. 2016
    • Harry Potter and the Cursed Child, the canonical continuation of the seven-book Potter saga, is not exactly a good play. It's a hot mess structurally, much of the dialogue is straight-up bad, and there are some truly stupid storytelling decisions that undermine the strengths of the series. But for all its flaws, Cursed Child is an important play: it's ambitious not only in its thematic concerns, but in its nature as a dramatic text rather than a novel. The significance of one of the most pivotal phenomenons in the history of literature switching the format of its presentation simply cannot be overstated. 
  • The Duchess of Malfi - John Webster, per. 1613/pub. 1623
    • John Webster is renowned as somewhat of a sadist among the early modern playwrights (hence the scene in Shakespeare in Love where a young Webster is torturing animals), and that's saying something when you're going up against the likes of Shakespeare, Marlowe, and Middleton; if you need to know why, look no further than The Duchess of Malfi. It's a savage drama of cruelty, betrayal, and corruption that makes the bloodbaths of Hamlet and Othello look like child's play—but Webster executes everything (literally) with his razor-edged dialogue and keen sense of structure. The Duchess of Malfi is a masterpiece that easily ranks against the best of Webster's talented contemporaries.