Musicals and Plays

51 Contemporary Plays Written After 2000

actors onstage in a contemporary play

Theater has always been a sign of the times — and we are living through an unprecedented period of social awakening and unrest. That’s reflected in contemporary plays, which offer heartbreaking insights and breathtaking hilarity in equal measure. The landscape of modern theater is expansive and often bizarre; you never know what you’re going to stumble upon.

Whether you’re looking for famous modern plays or contemporary comedic plays, we’ve got you covered. Each of our picks was written after 2000; you’ll find the date after each title, as well as a link to the license.

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Top image courtesy A.D. Players at the George under CC BY-ND 2.0

Best Contemporary Plays

Are you looking for new plays to read or perform? These are the best contemporary plays — from the best contemporary playwrights — of our time.

1. Anna in the Tropics (2003)

It’s 1929, and you’re a Cuban immigrant in a Florida cigar factory in Tampa. As you work long hours at this tedious job, a man called a lector reads aloud to you from the front of the room. This remarkable — and true-to-life — scene is the premise for the Pulitzer-Prize-winning Anna in the Tropics. Nilo Cruz shows off his magical, almost lyrical, grasp of language in this lovely play. As el lector reads Anna Karenina, the workers’ boring world is torn asunder, and their passions and tribulations come to a head. 

Playwright: Nilo Cruz
Licensing: Dramatists Play Service

2. 365 Days/365 Plays (2003)

365 Days/365 Plays isn’t a single modern play — as you might guess from the name, it’s a collection of 365 plays. In a truly remarkable feat, Suzan-Lori Parks wrote one play every day for a full year. Each story explores a different topic about what it means to be an American. Today, you can produce the full, year-long play cycle or a selection of performances.

Playwright: Suzan-Lori Parks
Licensing: Concord Theatricals

3. Almost, Maine (2004)

Almost, Maine has one of the most unusual stories of any contemporary play. The show was a smash hit when it premiered in Portland in 2004, but when it transferred to the off-Broadway Daryl Roth Theatre in 2006, it lasted just one month. In the years since, it’s become one of the most popular plays for high school and community theater groups. The reason? Perhaps the good-natured sweetness and innocent enthusiasm that radiates from each of the 11 vignette-style love stories. 

Playwright: John Cariani
Licensing: Dramatists Play Service

4. August: Osage County (2007)

The staunchly Midwestern Weston family seems normal on the surface. When the patriarch disappears, however, the crew gathers, and the truth bubbles hilariously to the surface. Letts infuses the script with subtle, brilliant insights — a few scenes in, your laughter will be tinged with heartbreak. The power of the writing was clear from the start; August: Osage County won the 2008 Pulitzer Prize for drama and ran for nearly two years on Broadway. It’s mounted frequently at theaters around the country, cementing its place as one of the most famous modern plays.

Playwright: Tracy Letts
Licensing: Dramatists Play Service

5. A Girl in School Uniform (Walks Into A Bar) (2018)

A girl is missing in a dystopian city. Danger is everywhere, and mysterious blackouts are setting residents on edge. The title might be pithy, but A Girl in School Uniform (Walks Into A Bar) is anything but a comedy. It’s an intense, uncomfortable look at the way women are treated, both in this sort-of futuristic place, but also in our modern world.

Playwright: Lulu Raczka
Publisher: Bloomsbury

6. Becky Shaw (2008)

If you’re looking for witty contemporary plays to read, it’s hard to do better than Becky Shaw. Sharp and more than a little cynical, this fast-paced contemporary comedic play stands out in any theatrical season. The plot centers on a first date and the bizarre relationship that follows. The characters are flawed and funny…and you’ll be glad you don’t have to hang out with them in real life. Push through the discomfort, and it’s not hard to see why this play was a runner-up for the Pulitzer Prize for Drama in 2009.

Playwright: Gina Gionfriddo
Licensing: Dramatists Play Service

7. Blackbird (2005)

With a cast of just three, Blackbird is intimate and intense. This is not a play for the faint of heart — it follows the meeting of a predator and his victim, now grown up. The premise is exactly as devastating as it sounds; it’s almost unbearable in parts. After premiering at the Edinburgh International Festival, this play went on to win the Olivier award for Best New Play and the Tony for Best Revival of a Play.

Playwright: David Harrower
Licensing: Dramatists Play Service

8. Bootycandy (2011)

Bootycandy explores what it’s like to grow up as a Black gay man. Inspired by the real childhood of playwright Robert O’Hara, the script is simultaneously funny and poignant. It takes stereotypical scenes and tropes and adds an irreverent, ebullient twist. The result is a curious patchwork of sketches and scenes — it works best when you accept the unusual form and enjoy the ride.

Playwright: Robert O’Hara
Licensing: Concord Theatricals

9. Clybourne Park (2010)

If you’re in search of comedic contemporary plays, Clybourne Park fits the bill — it racked up Tony, Olivier, and Pulitzer awards. This play might sound like a Jane Austen novel, but it’s actually a sequel to A Raisin in the Sun. Though the script dives into racial issues and prejudice, it does so with a deft hand; Norris manages to create a riotously funny, deliciously witty story. 

Playwright: Bruce Norris
Licensing: Dramatists Play Service

10. Cost of Living (2016)

Cost of Living explores the experiences of two physically disabled people, but don’t expect an uplifting story of triumph — the plot is firmly grounded in reality, with all of its uncomfortable and distressing truths. The script is nuanced and heart-rending, offering an in-depth look at privilege of all kinds.

Playwright: Martyna Majok
Licensing: Dramatists Play Service

11. “Daddy”: A Melodrama (2019)

Jeremy O. Harris shot to fame with Slave Play; with “Daddy”, he seems determined to shock audiences. You’ll meet Andre, a wealthy older art collector, and his much younger lover and protege, Franklin. When Franklin’s mother arrives, full of disapproval, conflict ensues. Despite the mixed reviews for “Daddy”, it’s an interesting and decidedly modern look at race and class conflicts in the world of art.

Playwright: Jeremy O. Harris
Licensing: Not available

12. Doubt: A Parable (2004)

The dark secrets of a Catholic school come to the surface in this deep, moving contemporary play from John Patrick Shanley. Two nuns, a priest, and the mother of a young student tell the story of potential abuse — and the doubt that surrounds the accusation. Shanley’s nuanced writing is sure to have you questioning yourself and your assumptions at every turn. Doubt: A Parable took home a Pulitzer in 2005; the Broadway production won a Tony the same year. Look out for a production at a university near you — Doubt has become one of the most popular contemporary plays for college students.

Playwright: John Patrick Shanley
Licensing: Dramatists Play Service

13. Elliot, a Soldier’s Fugue (2006)

You might recognize Quiara Alegría Hudes’ name — she wrote the book for the musical In the Heights. In Elliot, a Soldier’s Fugue, Hudes takes another look at the tradition of wartime service in different generations of a Puerto Rican family. As the title character returns from a second tour in Iraq at age 19, he discovers how his trauma parallels that of his father and grandfather. The storytelling is abstract, so it requires some concentration; get a sense of the vibe here.

Playwright: Quiara Alegría Hudes
Licensing: Dramatists Play Service

14. Enron (2009)

A corporate collapse might not seem like fertile fodder for a play, but Enron takes it on with glee. Energetic and fast-paced, this modern play follows CEO Jeffrey Skilling through the company’s wild rise and fall. You might even learn a thing or two; Prebble manages to make complicated concepts feel more accessible. (Or, if Ben Brantley is to be believed, “lucid to the point of simple-mindedness”.)

Playwright: Lucy Prebble
Licensing: Dramatists Play Service

15. Fairview (2018)

On the surface, Fairview seems like a relatively standard family drama. The Frasiers, a Black family, are getting ready for a family birthday party, but nothing is proceeding according to plan. Between day drinking and teenage drama, everything is going off the rails. Then comes Act 2 — the action begins again, this time observed and commented on by a group of white characters. (And it doesn’t stop there.) The curious structure is a surprisingly effective way to illuminate issues of racial disparity and prejudice.

Playwright: Jackie Sibblies Drury
Licensing: Dramatists Play Service

16. God of Carnage (2006)

Despite its epic title, God of Carnage revolves around a schoolyard conflict between two boys. When the parents meet, purportedly to resolve the issue, the discussion devolves into madness. This contemporary play is equal parts funny and tragic, revealing the wild passions and anger that flow beneath a seemingly civilized middle-class life.

Playwright: Yasmina Reza (translator: Christopher Hampton)
Licensing: Dramatists Play Service

17. Heroes of the Fourth Turning (2019)

If you’re exhausted from the constant political “discourse” (we’re using that term loosely) that’s everywhere, maybe give Heroes of the Fourth Turning a pass. If you have the mental space however, this insightful play is well worth a read. It follows a group of opinionated Catholic conservatives — they’re intellectuals, so the discourse won’t leave you feeling bereft of brain cells — as they reunite in their Wyoming college town. The play is a captivating meditation on modern politics, art, and religion.

Playwright: Will Arbery
Licensing: Concord Theatricals

18. HIR (2015)

People who grow up in a family with an unbalanced power dynamic often wonder what it would be like if the hierarchy was inverted. That’s exactly what happens in HIR — Isaac returns home to discover that his abusive father, after having a stroke, is under the control of his now-liberated mother. His younger sibling has come out as transgender, and the two are on a mission to take down the patriarchy. Mac’s signature “absurd realism” style contributes nicely to this dark comedy.

Playwright: Taylor Mac
Licensing: Dramatists Play Service

19. I Am My Own Wife (2003)

Based on the wild life of Charlotte von Mahlsdorf, I Am My Own Wife is a one-person play about a German transvestite who lived from 1928-2002. After killing her father (a prominent Nazi) with a rolling pin, von Mahlsdorf went on to survive some of the most difficult decades in recent history. She became a central figure in the Berlin gay community. Wright’s Pulitzer-winning play celebrates von Mahlsdorf’s remarkable life — she dressed in drag and collaborated with the Stasi to survive — in a sensitive and ultimately affectionate manner.

Playwright: Doug Wright
Licensing: Dramatists Play Service

20. In the Next Room (or The Vibrator Play) (2009)

Though the title might sound modern, In the Next Room (or The Vibrator Play) takes you back to the late 1880s. This is a contemporary play set in Victorian times, when male doctors lavished the “diagnosis” of hysteria on female patients. The treatment? Orgasms. (Hence, the title.) The wildest part about the story is that it’s based in fact. This Pulitzer and Tony finalist isn’t shocking; rather, it’s funny and surprisingly sensitive.

Playwright: Sarah Ruhl
Licensing: Concord Theatricals

21. Indecent (2015)

It’s 1906, and Sholem Asch has just finished writing the shocking God of Vengeance, a play Yiddish play about the love affair between two women. Indecent traces the life of the play through history, jumping from the first performance in Berlin to the 1923 Broadway premiere, when the ensemble is arrested on charges of obscenity. It continues to a covert reading in Nazi-controlled Poland, and ends with a proposed version at Yale in the 1950s. The script offers an intimate look at the actors and the challenges of the day in each production. Emotion, history, and passion combine in this remarkable theatrical accomplishment.

Playwright: Paula Vogel
Licensing: Dramatists Play Service

22. Man from Nebraska (2003)

Ken (a man from Nebraska, of course) deals with a spiritual crisis in Tracy Letts’ play. On the advice of his pastor, he leaves Lincoln and ventures out into the wide world for the first time, landing in London. Navigating new relationships and inevitable temptations, Ken’s — supposedly missing — faith is tested. This sweet show is funny and good-hearted; balm for any struggling soul.

Playwright: Tracy Letts
Licensing: Dramatists Play Service

23. Omnium Gatherum (2003)

Omnium Gatherum — not to be confused with the Finnish death metal band of the same name — is a fast-paced, funny play. It’s shortly after 9/11, and an eclectic assortment of guests has gathered for a Manhattan dinner party. (You might recognize the characters; they’re all proxies for well-known cultural icons.) Conversation and arguments rise and fall as the cast processes the horrifying events and the broader implications on the world at large.

Playwrights: Theresa Rebeck, Alexandra Gersten-Vassilaros
Licensing: Concord Theatricals

24. On Every Link a Heart Does Dangle; or Owed (2019)

If you want a hard-to-find contemporary play, look no further than On Every Link a Heart Does Dangle; or Owed. It’s a fascinating reimagining of the Oedipus Rex story. Oedipus isn’t the central figure; instead, the story focuses on Mellie, a woman with a disability that has alienated the gods and the town of Thebes. Since the men have failed the city, Mellie and the other women must become its saviors.

Playwright: Tim J. Lord
Licensing: Not available (read an excerpt)

25. Rabbit Hole (2006)

Rabbit Hole explores the crushing effects of grief on a family. After an unthinkable tragedy, the Corbetts struggle to survive, each on their own way. This Pulitzer-winning play isn’t saccharine or melodramatic, but heartbreakingly honest; anyone who has ever walked (or crawled) through the valley of the shadow will find connection to the emotional story.

Playwright: David Lindsay-Abaire
Licensing: Dramatists Play Service

26. Ruined (2008)

Civil war is raging in the Democratic Republic of the Congo, and Mama Nadi is trying to keep her head above water. She runs a brothel that takes in women who have been “ruined” by soldiers. Inspired by Lynn Nottage’s interviews with real-life survivors in Africa, the story explores the impossibly complex and questionable decisions that women must make to survive in a world destroyed by men. It’s exactly as crushing as you might imagine, but it’s not without a note of hope.

Playwright: Lynn Nottage
Licensing: Dramatists Play Service

27. Sing Yer Heart Out for the Lads (2002)

If you love sports and controversy — doesn’t hurt to love British football, too — Sing Yer Heart Out for the Lads is an interesting contemporary read. It’s set in 2000, but the story rings disconcertingly true for modern day. After the British team loses, a group of fans in a pub let go of their filters. The racist, xenophobic, and misogynist dialogue is uncomfortably familiar. It’s a chilling warning of the dangers of nationalism.

Playwright: Roy Williams
Licensing: Concord Theatricals (UK)

28. Slave Play (2018)

Slave Play is a fearless and unexpected examination of race and sex. Three interracial couples attend an “Antebellum Sexual Performance Therapy” workshop at the McGregor Plantation. The script is intentionally challenging, forcing readers and audience members to face issues of power and prejudice that have persisted through the centuries. During the 2019 New York run, Vox called it “the most controversial show on Broadway.” Slave Play got 12 Tony nominations — an impressive feat for any playwright, but a particularly exceptional one considering that Harris wrote the play during his first year at Yale.

Playwright: Jeremy O. Harris 
Licensing: Concord Theatricals

29. Straight White Men (2014)

It’s Christmas, and four — you guessed it — straight white men have gathered in their middle-class Midwestern home to celebrate. The four are all contending with different life issues, all the while fully aware of their privileged position (thanks to the absent mother). It’s an interesting, and sometimes opaque, examination of the psychology of modern straight white males.

Playwright: Young Jean lee
Licensing: Dramatists Play Service

30. Take Me Out (2002)

The all-male Take Me Out tells the story of baseball player Darren Lemming. After he casually comes out as gay at a press conference, Lemming believes everything will be fine. When a racist and bigoted pitcher joins the team, everything descends into chaos. The main plot is fine, but the real delight is in the sweet subplot that features Lemming’s accountant falling in love with the game.Take Me Out is fun and snappy; it won the Tony Award for Best Play in 2003

Playwright: Richard Greenberg
Licensing: Dramatists Play Service

31. Sweat (2015)

Poverty is a popular topic for modern playwrights — in Sweat, Lynn Nottage follows this trend, examining the lives of a group of struggling blue-collar workers in Reading Pennsylvania. She deftly integrates the social and political context of the time, offering insights into the attitudes and behaviors of her characters. It’s not uplifting — the characters’ anger and bitterness jump off the page — but it’s certainly illuminating.

Playwright: Lynn Nottage
Licensing: Dramatists Play Service

32. War Horse (2007)

War Horse is about — you guessed it — a horse that goes to war. The script is based on a children’s novel, and it shows; it’s simple, emotional, and undeniably moving. (Maybe a little too sentimental, but that can be forgiven considering the source material.) The true magic of this play happens in the staging, which utilizes puppets with cage-style construction.

Playwright: Nick Stafford, Michael Morpurgo
Licensing: Oxford Playscripts

33. The History Boys (2004)

Don’t let the sharp wit and breezy dialogue of The History Boys food you — this charming play has plenty to say. It’s one of those modern plays that’s so easy to watch that the raw moments hit you that much harder. Set at a boys’ school in England, the plot follows a group of students as they prepare for exams, learning about the ramifications of history and the realities of life along the way.

Playwright: Alan Bennett
Licensing: Concord Theatricals

34. Topdog/Underdog (2001)

Topdog/Underdog is one of the best contemporary plays from one of the most celebrated modern playwrights: Suzan-Lori Parks. In fact, it won the Pulitzer Prize for Drama in 2002. Brothers Lincoln and Booth — yes, the names are intentional — are just trying to stay afloat after a challenging upbringing. Lincoln wants to make an honest living, but Booth can’t help but bring him down. This is a tale of sibling rivalry — the kind that comes with devastating consequences.

Playwright: Suzan-Lori Parks
Licensing: Dramatists Play Service

35. The Curious Incident of the Dog in the Night-Time (2012)

It’s 7 minutes after midnight, and 15-year-old Christopher Boone has made a horrifying discovery — his neighbor’s dog has been murdered with a garden fork. Christopher, who is somewhere on the autism spectrum (the story doesn’t give a clear diagnosis), is determined to solve the mystery. The Curious Incident of the Dog in the Night-Time, which is based on the Mark Haddon novel of the same name, gives readers a peek into Christopher’s ultra-logical view of the world. It’s poignant, funny, and worth a read.

Playwright: Mark Haddon, adapted by Simon Stephens
Licensing: Dramatists Play Service

36. Water by the Spoonful (2011)

You might remember Quiara Alegría Hudes from her play Eliot, a Soldier’s Fugue; in this follow-up, she again tackles the struggles of soldiers returning from war. Addiction, trauma, and family relationships intertwine — as in life — painting a crushing picture of people who are simply trying to hang on. When you’re in the right headspace, it’s a rich and rewarding journey.

Playwright: Quiara Alegría Hudes
Licensing: Dramatists Play Service

37. The Goat, or Who Is Sylvia? (2002)

Well, here’s a plot point you won’t be expecting — a man falls in love with a goat. Yes, you read that correctly. The Goat, or Who Is Sylvia? is an unexpected offering from Edward Albee. It’s not meant to be an outrageous comedy; rather, Albee explores human proclivities with distressing honesty. It’s decidedly uncomfortable; when it played on Broadway, many audience members simply left the theater. Is the subject matter one that deserves to be enshrined in play? (Or awarded a Tony, for that matter) That’s up to you to decide.

Playwright: Edward Albee
Licensing: Dramatists Play Service

38. Vanya and Sonia and Masha and Spike (2012)

Modern playwrights are dogged in their exploration of bleak, unpleasant material, but in Vanya and Sonia and Masha and Spike, Christopher Durang offers us a respite. Siblings (and roommates) Vanya and Sonia’s dull Chekhovian life is tossed upside down when their famous sister Masha comes to visit with her much younger (and much dumber) boyfriend Spike. Add in a cleaning lady who can see the future, and you have the recipe for a good time. When reviewing the 2013 Broadway production for the New York Post, Elisabeth Vincentelli commented, “this is the kind of full-on comedy that’s sadly rare on Broadway” — and we couldn’t agree more! 

Playwright: Christopher Durang
Licensing: Dramatists Play Service

39. The (curious case of the) Watson Intelligence (2013)

Madeleine George explores the Watsons of the world — as in Sherlock Holmes’ trusty assistant — and the roles they play in the most important developments in human history. This unusual and witty play jumps around in time, showcasing four different Watsons (both real and fictional, human and computer) and their Holmes-inspired counterparts. It’s a clever conceit, though some pairings are more fun than others. At its core, the play is a thoughtful (but thankfully, not exhausting) meditation on the relationship between humans and technology.

Playwright: Madeleine George
Licensing: Concord Theatricals

40. Bengal Tiger at the Baghdad Zoo (2009)

Lots of modern plays tell war stories, but they usually use a human perspective. In Bengal Tiger at the Baghdad Zoo, we get to see the war from a tiger’s perspective. The play has ghosts, prosthetic hands, and gold toilet seats — what more could you want? It’s a fascinating and engaging tale that offers a slightly lighter, yet still tragic, perspective. If you have the chance, catch a live production; it’s gripping, even in the hands of non-professionals.

Playwright: Rajiv Joseph
Licensing: Dramatists Play Service

41. One Man, Two Guvnors (2011)

One Man, Two Guvnors premiered in 2011, but it was originally conceived in 1743. (Isn’t theater grand?) Down-on-his-luck Francis takes jobs with a gangster named Roscoe and a snooty man named Stanley. What Francis doesn’t realize is that the real Roscoe is dead — he’s actually working for Roscoe’s sister, Rachel, who’s pretending to be her brother. To make matters worse, Rachel is in love with Stanley, her brother’s killer. This madcap comedy is laugh-out-loud funny.

Playwright: Richard Bean
Licensing: Dramatists Play Service

42. Yellow Face (2007)

Playwright David Henry Hwang calls Yellow Face an “unreliable memoir.” The story blends reality and fiction, following a character named DHH as he writes a play and protests the casting of Jonathan Pryce as the Engineer in Miss Saigon — something that actually happened in 1991. With humor and hope, the play examines how the entertainment industry has dealt with issues of race. It’s not at all preachy; after speaking out publicly, DHH himself ends up making a poor casting choice and finding a creative way to deal with the consequences.

Playwright: David Henry Hwang
Licensing: Dramatists Play Service

43. The Ferryman (2017)

It’s 1981, and the Carney family is celebrating the harvest at their farm in Northern Ireland. Quinn, a former soldier in the Irish Republican Army, receives a menacing visit from an IRA leader. The body of Quinn’s brother, who disappeared after Quinn left the group, has turned up, and the IRA wants to avoid any accusations. With this reality hanging over the gathering, each family member begins to spin their tale. It’s a big, lively masterpiece of storytelling that’s just as enjoyable on the page as it is on stage.

Playwright: Jez Butterworth
Licensing: Nick Hern Books

44. What the Constitution Means to Me (2017)

Part autobiography, part history lesson, part social commentary, What the Constitution Means to Me is one of the most unusual contemporary plays on our list. It’s largely a one-woman show — playwright Heidi Schreck performed in the original productions — that examines issues that face women. Without being heavy handed or boring, Schreck tackles everything from abuse to the people who are ignored by the Constitution (hint: it’s most of us). The script, which is designed to feel improvised, has a bit of a Leslie Knope vibe.

Playwright: Heidi Schreck
Licensing: Concord Theatricals

45. The Intelligent Design of Jenny Chow

Witty and charmingly outlandish, The Intelligent Design of Jenny Chow offers a fresh, surprisingly insightful take on the human vs. technology theme. Our leading lady is Jennifer, a young, agoraphobic tech whiz who’s afraid to leave her room. She longs to find her birth mother in China, so she creates a robot twin named Jenny Chow to tackle the quest on her behalf. The script isn’t without its flaws, but it’s funny, touching, and worth a read.

Playwright: Rolin Jones
Licensing: Dramatists Play Service

46. Blink (2013)

Blink is an intimate, quirky little romantic comedy — don’t worry, it’s not too sweet. There are just two characters, and they never interact or meet face-to-face; all communication happens over a baby monitor. Though it was written in 2013, an all-too-familiar sense of isolation permeates the play. It’s funny, heartbreaking, and more than a little unusual; playwright Phil Porter invented a unique structure that reflects the simplicity and naivete of the characters. 

Playwright: Phil Porter
Licensing: Concord Theatricals

47. Revolt, She Said, Revolt Again (2016)

If you’re tired of violence against women being used as a plot device in theater, film, and TV, Revolt, She Said, Revolt Again is a must-read. This contemporary play knows that we’re not safe, even in the theater — and it reacts with a ferocious roar of rage, lambasting the ways women are (still!) oppressed and dismissed. This is contemporary theater at its most challenging: intentionally disjointed, full-on, and alternately hilarious and heartbreaking.

Playwright: Alice Birch
Licensing: Concord Theatricals

48. The Hot Wing King (2020)

The premise of The Hot Wing King is simple; Cordell is out to win an annual hot wing competition in Memphis. As he perfects his recipe, the chaos of his chosen and biological family swirls around him in the kitchen. Hall, who also wrote the book for Tina: The Tina Turner Musical, was inspired by her brother — a Black, gay man living life in the south. This contemporary play is infused with Hall’s natural, easy style; you’re almost certain to recognize the endearing characters. Though critics described the plot as “lopsided” and “meandering” (and it is both), this new play won the 2021 Pulitzer Prize for Drama.

Playwright: Katori Hall
Licensing: Dramatists Play Service

49. The Flick (2013)

The Flick is a monster of a play; it runs for 3 hours. Given the generally understated nature of the writing — and the mundane movie-theater setting — it feels like a lot. This isn’t a play for the TikTok generation; it forces you to stretch out your attention span for the occasional low-key but insightful payoff. Unsurprisingly, audiences and critics had a mixed reaction to the protracted Chekhovian theatrical experience (the first act alone clocked in at nearly 2 hours), but the strong writing won out; Baker came away with the 2014 Pulitzer.

Playwright: Annie Baker
Licensing: Concord Theatricals

50. Escaped Alone (2016)

“A summer tea party on the brink of doom” is how one production of Escaped Alone described the play. Caryl Churchill cleverly uses four chatty, retired British women as the voice that warns of the coming apocalypse. It’s bizarre but entertaining, though the revelation of the women’s darkest secrets seems like an unnecessary addition to an already interesting show. The play runs for less than an hour, which is just the right length; it provides enough time to absorb the jarring content, but not enough for viewers and readers to tire of the conceit.

Playwright: Caryl Churchill
Licensing: Concord Theatricals

51. An Octoroon (2010)

In 1859, an Irish playwright wrote a play (The Octoroon) about slavery in the United States; An Octoroon tells the story of a modern playwright trying to rewrite the original show. It examines the various problems in the script, discusses race as a social construct, and explores the idea of blackface (and whiteface and redface) to pinpoint exactly what’s upsetting about it. The result is one of the most inventive and insightful contemporary plays out there.

Playwright: Branden Jacobs-Jenkins
Licensing: Dramatists Play Service