The 38 best challenging plays

Each point of light is one of the 38, placed by how hard it is to read. The brighter, the higher it ranks. The dotted line is one way up.

38
books
252
hours to read
6
free to read here
Challenging18 booksDifficult20 books

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No. 1 of 38

Hamlet

William Shakespeare · 1601

Difficulty 67/1003.1 hours

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Readable here · 6

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Showing 38 books

About 252 hours for 38 of 38 books with measured lengths. Estimates use 250 words a minute, adjusted for each book's difficulty. At 2 hours a day, about 127 days for those books.

1–10 · 49 hours
  1. No. 1 on this list. Hamlet

    William Shakespeare · 1601

    Challenging3.1 hours

    Taught in schools: Uzbek adabiyot curriculum (Uzbekistan)

    Included in: Bokklubben World Library, Great Books of the Western World, UNESCO Collection of Representative Works

    Shakespeare invented the modern soliloquy here: a mind watching itself think, stalling, doubting, performing. Every fictional character who hesitates before acting is Hamlet's descendant.

  2. No. 2 on this list. King Lear

    William Shakespeare · 1606

    Difficult12 hours

    Taught in schools: AQA GCSE and A-level English Literature (UK), WJEC/Eduqas GCSE and A-level English Literature (UK)

    Included in: Bokklubben World Library, Great Books of the Western World, UNESCO Collection of Representative Works

    King Lear appears on 2,254 university syllabi per Open Syllabus — placing it in the 84th percentile of all works — and has Wikipedia articles in 71 languages. It appears in virtually every anthology of English literature and every Shakespeare course worldwide. Most critics rank it alongside Hamlet as Shakespeare's greatest achievement; Harold Bloom called it the summit of the Western literary canon.

  3. No. 3 on this list. Waiting for Godot

    Samuel Beckett · 1953

    Difficult2.4 hours

    Included in: Great Books of the Western World

    Waiting for Godot appears on virtually every comparative literature, modern drama, and theater studies syllabus worldwide, and is listed in Open Syllabus's Top 500 Literature titles. The Wikipedia article exists in 68 languages, and the play has been continuously performed since its 1953 Paris premiere. Le Monde named it among the 100 Books of the Century. It is as canonical as any play written after Shakespeare.

  4. No. 4 on this list. Faust

    Johann Wolfgang von Goethe · 1832

    Challenging3.9 hours

    Taught in schools: Turkish edebiyat curriculum (Turkey)

    Included in: Bokklubben World Library, Great Books of the Western World

    Goethe spent sixty years building a dramatic poem in which a scholar sells his soul not for pleasure but for the experience of a moment worth stopping time for. The work became the central myth of modernity: the idea that striving itself, not arrival, is what redeems a human life.

  5. No. 5 on this list. Antony and Cleopatra

    William Shakespeare · 1607

    Challenging2.7 hours

    Taught in schools: WJEC/Eduqas GCSE and A-level English Literature (UK)

    Included in: Great Books of the Western World

    Antony and Cleopatra appears on virtually every Shakespeare survey and major tragedy course in English-speaking universities. It is included in all complete works editions — Oxford, Arden, Folger, Norton — and features on most 'essential Shakespeare' reading lists. While taught less frequently than Hamlet or King Lear, it holds permanent status as one of the four or five major late tragedies.

  6. No. 6 on this list. A Streetcar Named Desire

    Tennessee Williams · 1947

    Challenging2.3 hours

    Taught in schools: AQA GCSE and A-level English Literature (UK), Cambridge IGCSE Literature in English (0475), UNAM Escuela Nacional Preparatoria – programas de Literatura (Mexico)

    Required reading in virtually every American literature curriculum, from high school through university, and among the most-produced plays in the American theater canon. It appears on nearly every 'great American plays' list alongside Death of a Salesman, and has been continuously performed since its 1947 Broadway premiere.

  7. No. 7 on this list. Death of a Salesman

    Arthur Miller · 1949

    Challenging3.9 hours

    Taught in schools: AQA GCSE and A-level English Literature (UK), Common Core text exemplars (Appendix B) (US), CSEC English B – Caribbean Examinations Council

    Required reading in virtually every American high school and most university American Drama and Literature courses. The play appears on thousands of university syllabi globally and consistently ranks among the defining works of American theater on 'essential reading' lists. It has been in continuous production since its 1949 premiere.

  8. No. 8 on this list. Troilus and Criseyde

    Geoffrey Chaucer · 1385

    Difficult9.3 hours

    Included in: Great Books of the Western World

    Required reading in virtually every medieval English literature curriculum, taught across English, Comparative Literature, and Medieval Studies programs at universities worldwide. Though Open Syllabus data is unavailable here, Chaucer courses built around this text are standard at every major university with an English department. It holds a place among the most-studied long poems in the English language.

  9. Peer Gynt is a cornerstone of the Scandinavian theatrical canon and is regularly staged worldwide, from the National Theatre to major European opera houses. Edvard Grieg's 1876 incidental music gave the work cultural reach extending far beyond theatre audiences. It appears on world drama syllabi internationally and is central to any survey of 19th-century European literature.

  10. No. 10 on this list. Cat on a Hot Tin Roof

    Tennessee Williams · 1955

    Challenging5.5 hours

    Taught in schools: AQA GCSE and A-level English Literature (UK)

    Cat on a Hot Tin Roof won the 1955 Pulitzer Prize for Drama and is taught in American literature and theater courses across the country, standing alongside A Streetcar Named Desire as the twin peaks of Williams's canon. The 1958 film adaptation with Paul Newman and Elizabeth Taylor brought it to global audiences, cementing its place in the broader cultural record. It appears on virtually every syllabus covering American drama.

11–20 · 76 hours
  1. No. 11 on this list. The Theatre and Its Double · Antonin Artaud · 1938

    Listed among Le Monde's 100 Books of the Century (1999) and the Open Syllabus Top 500 in Literature, with Wikipedia presence in 10 languages. The Theatre and Its Double is essential reading in theatre studies programs worldwide. Published by NYRB Classics. Every contemporary theatre practitioner and scholar encounters Artaud's theories in courses on performance studies, avant-garde theatre, modernism, and cultural theory.

    Difficult11 hours

    Start this book
  2. No. 12 on this list. The Caucasian Chalk Circle · Bertolt Brecht · 1948

    The Caucasian Chalk Circle is among the most-taught plays in university drama and literature curricula worldwide, standard on syllabi alongside Mother Courage and The Good Person of Szechwan. It appears in secondary school programs across Europe and is a fixture of Western dramatic canon, placing it well above mid-century works that lack similar educational penetration.

    Difficult4.7 hours

    Start this book
  3. No. 13 on this list. Life of Galileo · Bertolt Brecht · 1943

    Life of Galileo is a cornerstone of the Brechtian canon and a fixture on university syllabi worldwide — taught in drama programs, literature departments, and philosophy of science courses alike. Brecht's five-scene structure and the figure of Galileo recanting before the Inquisition appear in virtually every survey of modern drama, placing this work well above mid-tier literary status.

    Challenging15 hours

    Start this book
  4. No. 14 on this list. The Good Person of Szechwan · Bertolt Brecht · 1943

    The Good Person of Szechwan is Brecht's third most frequently taught and produced major work after Mother Courage and The Caucasian Chalk Circle. It appears in virtually every university theatre and modern drama curriculum. The first professional productions starred Peggy Ashcroft (Royal Court, 1956) and Uta Hagen (Phoenix Theatre, New York, 1956). Giorgio Strehler's 1981 Milan production became a landmark of European theatre. It is canonical in both German studies and world theatre programs.

    Challenging14 hours

    Start this book
  5. No. 15 on this list. Angels in America: Perestroika · Tony Kushner · 1992

    Angels in America is taught in American theater, drama, and queer studies programs at universities across the country and is consistently listed among the essential works of 20th-century American literature. Both parts of the play appear regularly on syllabi in literature, political science, and history courses. Its status as a defining document of the AIDS crisis and Reagan-era America makes it required context for anyone studying the period.

    Difficult6.8 hours

    Start this book
  6. No. 16 on this list. Rosencrantz and Guildenstern Are Dead · Tom Stoppard · 1966

    Rosencrantz and Guildenstern Are Dead is a fixture of university theater and English literature curricula, appearing consistently on drama syllabi across English-speaking universities. It is widely taught alongside Waiting for Godot as a key postmodern, absurdist text. Its Wikipedia article exists in dozens of languages and includes dedicated reception and adaptations sections, and a 1990 film adaptation by Stoppard himself extended its cultural reach.

    Difficult3 hours

    Start this book
  7. No. 17 on this list. The Good Soldier · Ford Madox Ford · 1915

    Appears on 473 university syllabi (67th percentile in Open Syllabus), placing it firmly in the modernist teaching canon alongside Conrad and early Lawrence. Listed on the Modern Library 100 Best Novels. A standard text in courses on British modernism and narrative technique, though less universally assigned than Woolf or Joyce.

    Challenging7 hours

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  8. No. 18 on this list. Celestina · Fernando de Rojas · 1499

    Ranked immediately after Don Quixote in the Spanish canon, required reading in Spanish education and standard in medieval and Renaissance literature courses worldwide.

    Difficult9.8 hours

    Start this book
  9. No. 19 on this list. Miss Julie · August Strindberg · 1888

    Miss Julie is required reading in virtually every drama curriculum globally and taught widely in comparative literature and theatre history courses. It is one of a handful of nineteenth-century plays — alongside works by Ibsen and Chekhov — that appear on nearly every list of essential modern drama. No syllabus data was available in the database, but its presence in world theatre canons is unambiguous.

    Challenging2 hours

    Start this book
  10. No. 20 on this list. Bohemian Lights · Ramón del Valle-Inclán · 1924

    Required reading in Spanish secondary education and the defining text of the esperpento in every account of modern Spanish theatre.

    Difficult2.8 hours

    Start this book
21–30 · 39 hours
  1. No. 21 on this list. Blood Knot · Athol Fugard · 1961

    Fugard's breakthrough play and a foundational work of South African theater. Widely taught and performed as a landmark of anti-apartheid drama.

    Difficult7 hours

    Start this book
  2. No. 22 on this list. The Women of Trachis · Sophocles · c. 450 BCE

    Included in: Great Books of the Western World

    Deianira waits in Trachis. Her husband Heracles has been gone fifteen months, fighting a war for reasons she suspects are not honorable, and she has heard nothing. When he finally sends word—along with a captive woman, Iole—Deianira understands what her husband has not bothered to say. She has one weapon left: a robe smeared with what the centaur Nessus told her, as he died from Heracles' arrow, was a love charm. She sends it. The robe, of course, is poison. Sophocles builds the tragedy not through deception but through sincerity: Deianira acts out of love, not malice, and destroys the man she was trying to keep. The Women of Trachis is the starkest of the surviving Sophocles plays—no redemption, no divine rescue, just Heracles screaming in agony and his son Hyllus forced to light his father's funeral pyre. The chorus of Trachinian women watches and mourns but cannot intervene. What makes this play unsettling is how ordinary Deianira's reasoning is. She is not catastrophically wrong; she simply cannot know. The gods know, and say nothing. Ezra Pound's 1954 translation, Trachiniae, turned the choral odes into American vernacular and introduced the play to modernist readers. Sophocles leaves Heracles' fate unresolved—death or apotheosis—and refuses to explain why the innocent suffer.

    Challenging7.2 hours

    Start this book
  3. No. 23 on this list. Forefathers' Eve · Adam Mickiewicz · 1832

    Taught in schools: Lektury obowiązkowe – Polish national reading list (Poland)

    Compulsory in Polish education and the most politically charged text in the Polish canon, though little known outside Slavic studies.

    Difficult5.8 hours

    Start this book
  4. No. 24 on this list. Arcadia · Tom Stoppard · 1993

    Arcadia is widely regarded as one of the finest English-language plays of the twentieth century and appears on drama syllabi at most anglophone universities. The play lacks the database signals (no syllabus count, no Wikipedia data retrieved), but from general knowledge it is a fixture of British drama courses and has been continuously staged in London and New York since its 1993 premiere. It ranks below Hamlet or Waiting for Godot in canonical weight but above most contemporary drama.

    Difficult5.7 hours

    Start this book
  5. No. 25 on this list. The Father · August Strindberg · 1887

    No syllabus or Wikipedia data was returned by automated signals, but 'The Father' is widely anthologized in world drama collections and taught in comparative literature and theatre history courses alongside Ibsen. It is one of Strindberg's two most canonical plays, a fixture of naturalist drama curricula internationally.

    Challenging4.1 hours

    Start this book
  6. No. 26 on this list. Childe Roland to the Dark Tower Came · Robert Browning · 1855

    A fixture of Victorian poetry surveys and Browning units in university curricula, regularly anthologized in collections like the Norton Anthology of English Literature. No syllabus or Wikipedia data was returned by the database for this work, so this score rests on its well-documented standing as one of Browning's most consistently taught single poems, short of universal fixtures like Hamlet or Gatsby.

    Challenging11 min

    Start this book
  7. No. 27 on this list. Hayavadana · Girish Karnad · 1971

    A standard text in Indian drama and world-theatre courses and the key example of the theatre of roots movement.

    Challenging1.8 hours

    Start this book
  8. No. 28 on this list. A Number · Caryl Churchill · 2002

    One of Churchill's most frequently performed plays and a standard text in contemporary drama courses. Widely recognized as a landmark of twenty-first-century theater.

    Difficult58 min

    Start this book
  9. No. 29 on this list. The Wedding · Stanisław Wyspiański · 1901

    Taught in schools: Lektury obowiązkowe – Polish national reading list (Poland)

    Compulsory in Polish schools and the single most performed Polish play, though little known outside Central Europe.

    Difficult2.7 hours

    Start this book
  10. No. 30 on this list. Kordian · Juliusz Słowacki · 1834

    Taught in schools: Lektury obowiązkowe – Polish national reading list (Poland)

    Compulsory in Polish schools and a standard text of Romantic drama in Slavic studies, with little presence beyond.

    Difficult3.1 hours

    Start this book
31–38 · 88 hours
  1. No. 31 on this list. The Un-Divine Comedy

    Zygmunt Krasiński · 1835

  2. No. 32 on this list. Pierre

    Herman Melville · 1852

  3. No. 33 on this list. Judas

    Amos Oz · 2017

  4. No. 34 on this list. The Reader

    Bernhard Schlink · 1995

  5. No. 35 on this list. Requiem for a Nun

    William Faulkner · 1951

  6. No. 36 on this list. The Sign in Sidney Brustein's Window

    Lorraine Hansberry · 1964

  7. No. 37 on this list. We Need to Talk About Kevin

    Lionel Shriver · 2005

  8. No. 38 on this list. The Dynasts

    Thomas Hardy · 1908

About this list

These 38 books are the highest-scoring eligible challenging plays currently in the catalogue. By literary regard, it opens with Hamlet, King Lear and Waiting for Godot. About 252 hours of reading in all. Difficulty runs from 67 to 75 out of 100 for the middle half of the list; the summit is Troilus and Criseyde at 79.

This list is ranked by literary regard, with a consistent order for equal scores. Membership follows authors and co-authors, not translators or editors. Catalogue coverage and the historical canon both limit what this list can represent, and genre labels are the catalogue’s own, gathered into broader kinds.

When we matched the Canons dataset to our catalogue in October 2026, our canonical-status scores rose with the number of school curricula, publisher series and lists in it that cite a work: the median score was 72 for books one such source cites, 84 at two, 88 at three, 92 at four and 93 at five or more. Prizes are left out of that count. Outside the state curricula, the dataset’s sources choose mostly from what has been translated into English or French, so it is a weaker check on other literatures. Source: Canons (Andrew Piper), CC BY 4.0

Questions people actually ask

What are the best challenging plays?
By literary regard, which weighs canonical status, critical standing and influence, Hamlet, King Lear, Waiting for Godot, Faust and Antony and Cleopatra lead. ReadingRate ranks 38 such books, each with a difficulty score and a reading-time estimate.
Where should I start with challenging plays?
Start from difficulty, not from rank. The most approachable books on this list that still carry top literary regard are The Good Soldier by Ford Madox Ford (about 7 hours), Miss Julie by August Strindberg and The Good Person of Szechwan by Bertolt Brecht.
How hard are challenging plays to read?
Most of this list sits between 67 and 75 on ReadingRate's 100-point difficulty scale, where 40 to 55 is moderate. The summit is Troilus and Criseyde at 79. Every entry carries its own score, so a reader can pick a great book at a difficulty they will finish.
How is this list ranked?
On literary-regard data: how canonically established a work is, its critical standing, and its influence on later writing. It is not a readers’ poll, which is why recent bestsellers rarely appear. Membership follows authors and co-authors, not translators or editors. A list that is not a genre list keeps to literature (fiction, poetry, drama and philosophy), with philosophy taking no more than one slot in five while there is literature left to rank; every list holds at most three works by one author.