139 Great Difficult Books to Crack Your Brain

The original list was derived from a very interesting topic in reading group on the Goodreads site called Brain Pain. It looked so fascinating that I wrote all the authors and books down because really these are same of the greatest books out there. If you read anything on this list, you’re reading a great book. A lot of them are absolutely classics. It’s not a list of easy reading books though, as the books were specifically chosen for their difficulty. Looking down at the 16 books I’ve read on the list, most of them weren’t that hard, and some were downright easy reads.

Have you ready of the books below? Have you heard of any of them? Heard of any of the authors? Which books would you like to read below, assuming you had the time. Are there any errors in my list below. Gimme some feedback, you slackers.

139 Great Difficult Books to Crack Your Brain

  1. Renata Adler, Speedboat, novel.
  2. Renata Adler, Pitch Dark, novel.
  3. Theodor W. Adorno, “The Culture Industry:  Selected Essays on Mass Culture,” book chapter.
  4. Aeschylus, The Oresteia, play.
  5. Ryūnosuke Akutagawa, “Rashomon,” short story.
  6. Ryūnosuke Akutagawa, “In a Grove,” short story.
  7. Isabel Allende*, Eva Luna, novel.
  8. Apuleius, The Golden Ass, play.
  9. Aristotle, Poetics, non-fiction.
  10. Aristotle, The Art of Rhetoric, non-fiction.
  11. Aristophanes, Lysistrata, play.
  12. Margaret Atwood, Cat’s Eye, novel.
  13. Erich Auerbach, Mimesis: The Representation of Reality in Western Literature, non-fiction.
  14. Jane Austen, Emma, novel.
  15. Gaston Bachelard, Air and Dreams: An Essay on the Imagination of Movement, non-fiction.
  16. Gaston Bachelard, The Poetics of Space, non-fiction.
  17. Djuna Barnes, Nightwood, novel.
  18. John Barth*, Giles Goat-Boy, novel.
  19. Charles Baudelaire, Les Fleurs du Mal Read
  20. Charles Baudelaire, Paris Spleen
  21. Charles Baudelaire, The Painter of Modern Life and Other Essays, non-fiction.
  22. Walter Benjamin, The Arcades Project, non-fiction.
  23. Jorge Luis Borges*, “The Cult of the Phoenix,” short story.
  24. Jorge Luis Borges, “The South,” short story.
  25. Richard Brautigan*, In Watermelon Sugar, novel.
  26. Charlotte Bronte, Jane Eyre, novel.
  27. Susan Buck-Morss, The Dialectics of Seeing: Walter Benjamin and the Arcades Project, non-fiction.
  28. Mighail Bulgakov, The Master and Margarita, novel.
  29. Dino Buzzati, The Tartar Steppe, novel.
  30. James M. Cain, Mildred Pierce, novel.
  31. Italo Calvino, If on a Winter’s Night a Traveler, novel.
  32. Albert Camus*, The Plague, novel.
  33. Angela Carter, The Bloody Chamber and Other Stories, short stories.
  34. Adolfo Bioy Casares, The Invention of Morel, novel.
  35. Robert Coover*, The Public Burning, novel.
  36. Julio Cortazar*, Hopscotch, novel, Read.
  37. Mark Z. Danielewski, House Of Leaves, novel.
  38. Marie Darrieussecq, Pig Tales: A Novel of Lust and Transformation, novel.
  39. Marie Darrieussecq, My Phantom Husband, novel.
  40. Don DeLillo, The Body Artist, novel.
  41. Fyodor Dostoevsky, Notes From Underground, novel.
  42. Rikki Ducornet, The Stain, novel.
  43. T.S. Eliot*, The Waste Land Read
  44. Euripides, The Trojan Women (The Women of Troy), play.
  45. Euripides, Medea, play.
  46. William Faulkner*, Absalom, Absalom!, novel.
  47. William Faulkner, The Sound and The Fury, novel.
  48. Juan Filloy, Op Oloop, novel.
  49. Charles Fourier, The Social Destiny of Man, or Theory of the Four Movements, non-fiction.
  50. Paula Fox, Desperate Characters, novel.
  51. Sigmund Freud, The Uncanny, non-fiction.
  52. William Gaddis, J R, novel.
  53. William Gaddis, The Recognitions, novel.
  54. Gabriel Garcia-Marquez, 100 Years of Solitude, novel, Read
  55. William Gass*, Middle C, novel.
  56. William Gass, Omensetter’s Luck, novel.
  57. William Gass, The Tunnel , novel.
  58. Johann Wolfgang von Goethe, Faust I & II, play.
  59. Gunter Grass*, The Flounder, novel.
  60. H. D., Helen in Egypt
  61. John Hawkes, The Lime Twig, novel.
  62. Nathaniel Hawthorne, The Scarlet Letter, A Romance, novel. Read.
  63. E. T. A. Hoffman, The Life and Opinions of the Tomcat Murr, novel.
  64. Siri Hustvedt, The Blazing World, novel.
  65. James Joyce*, A Portrait of the Artist as a Young Man, novel, Read.
  66. James Joyce, Ulysses, novel.
  67. Franz Kafka, Josephine the Singer, or The Mouse Folk, short story.
  68. Franz Kafka, The Metamorphosis, novella, Read.
  69. Anna Kavan, Asylum Piece, novel.
  70. Anna Kavan, Ice, novel.
  71. Yasunari Kawabata, Beauty and Sadness, novel.
  72. Comte de Lautréamont, The Songs of Maldoror, novel.
  73. Doris Lessing, The Golden Notebook, novel. Read
  74. Clarice Lispector, Água Viva, novel.
  75. Clarice Lispector, Near to the Wild Heart, novel.
  76. Malcolm Lowry, Under the Volcano, novel.
  77. David Mamet, Faustus, play.
  78. Thomas Mann, Doctor Faustus: The Life of the German Composer Adrian Leverkühn, Told by a Friend, novel.
  79. Christopher Marlowe, The Tragical History of Doctor Faustus, play.
  80. Karl Marx and Friedrich Engels, The Communist Manifesto , non-fiction, Read.
  81. Colman McCarthy, Blood Meridian, novel.
  82. Joseph McElroy, A Smuggler’s Bible, novel.
  83. James Michener*, The Novel, novel.
  84. Toni Morrison*, The Bluest Eye, novel.
  85. Nicholas Mosley, Impossible Object, novel.
  86. Harumi Murakami, 1Q84, novel.
  87. Harumi Murakami, Wind-Up Bird Chronicle, novel.
  88. Vladimir Nabakov*, Ada, or Ardor, novel.
  89. Vladimir Nabakov, Invitation to a Beheading, novel.
  90. Vladimir Nabakov, Lectures on Literature, non-fiction.
  91. Vladimir Nabakov, Lolita, novel Read
  92. Vladimir Nabakov, Pale Fire, novel.
  93. Vladimir Nabakov, Pnin, novel.
  94. Vladimir Nabakov, Speak, Memory, novel.
  95. Flann O’Brien, At Swim-Two-Birds, novel.
  96. George Perec, Life, a User’s Manual, novel.
  97. Fernando Pessoa, The Book of Disquietude, novel.
  98. Robert Pirsig, Zen & the Art of Motorcycle Maintenance, non-fiction, Read
  99. Sylvia Plath, The Bell Jar, novel.
  100. Marcel Proust, In Search of Lost Time, novel.
  101. Thomas Pynchon*, Against The Day, novel.
  102. Thomas Pynchon, Gravity’s Rainbow, novel, Read
  103. Thomas Pynchon, Mason & Dixon, novel.
  104. François Rabelais, Gargantua & Pantagruel, novel.
  105. Dorothy Richardson, Pilgrimage, Vol. 1: Pointed Roofs, novel.
  106. Alain Robbe-Grillet*, The Erasers, novel.
  107. Philip Roth*, The Breast, novel.
  108. Juan Rulfo, Pedro Páramo, novel, Read
  109. Salman Rushdie*, Midnight’s Children, novel.
  110. Ernesto Sabato, The Tunnel, novel.
  111. William Shakespeare*, Hamlet, play,  Read
  112. William Shakespeare, Macbeth, play,  Read
  113. Susan Sontag, Death Kit, novel.
  114. Susan Sontag, On Photography
  115. Susan Sontag, The Benefactor, novel.
  116. Sophocles, Antigone, play.
  117. Sophocles, Oedipus the King, play.
  118. Sophocles, Electra, play.
  119. Gilbert Sorrentino, Mulligan Stew, novel.
  120. Lawrence Sterne, Tristram Shandy, novel.
  121. Jonathan Swift, Gulliver’s Travels, novel. Read
  122. Enrique Vila-Matas, Dublinesque, novel.
  123. William Vollman*, Argall: The True Story of Pocahontas and Captain John Smith, novel.
  124. William Vollman, Europe Central, novel.
  125. William Vollman, Fathers and Crows, novel.
  126. William Vollman, The Ice-Shirt, novel.
  127. William Vollman, The Dying Grass, novel.
  128. William Vollman, The Rainbow People, non-fiction.
  129. William Vollman, The Rifles, novel.
  130. William Vollman, The Royal Family, non-fiction.
  131. David Foster Wallace, Infinite Jest, novel.
  132. David Foster Wallace, The Broom of the System, novel.
  133. Edmund White, The Flaneur: A Stroll through the Paradoxes of Paris, novel.
  134. Virginia Woolf, Mrs. Dalloway, novel.
  135. Virginia Woolf, Orlando, novel.
  136. Virginia Woolf, The Voyage Out, novel.
  137. Virginia Woolf, The Waves, novel.
  138. Virginia Woolf, To the Lighthouse, novel.
  139. Marguerite Young, Miss Macintosh, My Darling, novel.

I’ve read 16 out of 139. That works out to 1

Other Works by the Authors Above That I’ve Read Which Were Not on the List

The entries with an asterisk mean that I’ve read other works by them. This list includes 21 of the authors above, and adds 38 more works to the list, this time of works by one of the authors above that I have read that are not listed in the main list.

  1. Isabel Allende, The House of the Spirits
  2. John Barth, The Sot-Weed Factor and “Life-Story”
  3. Jorge Luis Borges, Ficciones and Labyrinths
  4. Richard Brautigan, A Confederate General in Big Sur and Trout Fishing in America
  5. Albert Camus, The Stranger
  6. Robert Coover, “A Pedestrian Accident”
  7. Julio Cortazar, “Blow Up”
  8. T.S. Eliot, All poetry
  9. William Faulkner, Light in August
  10. William Gass, “In the Heart of the Heart of the Country”
  11. Gunter Grass, The Dog Years
  12. James Joyce, Dubliners
  13. James Michener, The Bridges at Toko-Ri
  14. Toni Morrison, Beloved, Jazz, and The Sound of Solomon
  15. Vladimir Nabakov, Bend Sinister and “…If in Aleppo Once”
  16. Thomas Pynchon, “A Journey into the Mind of Watts”, Slow Learner, The Crying of Lot 49, V, and Vineland
  17. Alain Robbe-Grillet, Pour un Nouveau Roman (For a New Novel), Dans le Labyrinthe (In the Labyrinth), La Jalousie (Jealousy), Projet pour une Révolution à New York (Project for a Revolution in New York); Souvenirs du Triangle d’Or (Souvenirs of the Golden Triangle), Topologie d’une Cité Fantôme (Topology of a Phantom City), and Le Voyeur (The Voyeur)
  18. Philip Roth, Goodbye, Columbus and Portnoy’s Complaint
  19. Salman Rushdie, The Satanic Voices
  20. William Shakespeare, Romeo and Juliet
  21. William Vollman, Poor People

Books I Want to Read by the Authors in the First List

Both lists combined gives us 160 authors and 176 books. I’ve now read 54 out of the combined 176 books, which gives us 3

Here are the books listed above that I would possibly like to read at some point. I left out books that I just don’t want to read right now, and no, I don’t care about Greek playwrights or Aristotle or all the Fausts, sorry.

Notes say how I feel about possibly reading it, whether I am familiar with the author or not and if so how much, a bit about the book or author, it’s status as a classic or not, the country of the author and the period or year when the book was written,  whether I’ve read anything else by the author, and finally, length was noted and tallied for very long books, more as a warning than anything else. If there’s no page length after the entry, the book has less than 500 pages and can at least be read by the average human in a reasonable length, unlike the doorstops, which violate that principle.

  1. Theodor W. Adorno, “The Culture Industry: Enlightenment as Mass Deception”: Sounds heavy duty. German expat in the US, 1947. Never read him.
  2. Ryūnosuke Akutagawa, “Rashomon”: Yes, classic, Japan, 1915. I know little about this writer. Never read him.
  3. Ryūnosuke Akutagawa, “In a Grove”: Maybe, Japan, 1922.
  4. Erich Auerbach, Mimesis: The Representation of Reality in Western Literature: Maybe, supposedly a classic of type, but sounds heavy duty. 625 pages. I don’t know much about him, just hear his name in passing. German expat in Turkey, 1946. Never read him.
  5. Jane Austen, Emma: Yes, a classic from 1847 UK. Never read her.
  6. Gaston Bachelard, Air and Dreams: Maybe, sounds intense. I know very little about this author, France, 1943. Sigh. Never read him.
  7. Gaston Bachelard, The Poetics of Space: Same as above, France, 1958.
  8. Djuna Barnes, Nightwood: Absolutely! A classic from an American expat in the UK, 1936. Never read her.
  9. John Barth, Giles Goat-Boy: Quite possibly! I love Barth. But 700 pages! US, 1966.
  10. Charles Baudelaire, Paris Spleen: Oh yes. France, 1869.
  11. Charles Baudelaire, The Painter of Modern Life and Other Essays: Maybe so, I love Baudelaire. France, 1863.
  12. Walter Benjamin, The Arcades Project: Maybe sounds deep. German expat in Spain, 1940. 1,100 pages! I’m not real familiar with this man or his work. Never read him.
  13. Jorge Luis Borges, “The Cult of the Phoenix”: Probably, Argentina, 1952. I love Borges.
  14. Jorge Luis Borges, “The South”: Same, Argentina, 1953.
  15. Richard Brautigan, In Watermelon Sugar: Maybe, US, 1968. I love Brautigan.
  16. Charlotte Bronte, Jane Eyre: Yes, another classic from 1816 UK. Never read her.
  17. Susan Buck-Morss, The Dialectics of Seeing: Walter Benjamin and the Arcades Project: I dunno, sounds so intense. 550 pages. US, 1991. Never read her.
  18. Mighail Bulgakov, The Master and Margarita: Absolutely, all-time classic, USSR, 1936. Never read him.
  19. Dino Buzzati, The Tartar Steppe: For sure, a little known (in the US) classic from Italy 1940. I know almost nothing about this author, but you sure hear a lot about this book. Never read him.
  20. James M. Cain, Mildred Pierce: Probably, it’s a classic noir from the US 1941. Never read him.
  21. Italo Calvino, If on a Winter’s Night a Traveller: Oh yes, a classic for sure, Italy, 1981. Never read him.
  22. Albert Camus, The Plague: Definitely, famous classic from France 1946.
  23. Angela Carter, The Bloody Chamber and Other Stories: Maybe. I don’t know much about this writer. US, 1979. Never read her.
  24. Adolfo Bioy Casares, The Invention of Morel: Definitely, classic from Argentina 1940, friend of Borges. Never read him.
  25. Robert Coover, The Public Burning: Absolutely, another classic from the US, 1977. 550 pages. Read a short story.
  26. Mark Z. Danielewski, House Of Leaves: Certainly, a recent US classic from 2000. Bizarre, baffling, and innovative. 700 pages! Never read him.
  27. Marie Darrieussecq, Pig Tales: A Novel of Lust and Transformation:  France, 1996. Never read her.
  28. Comte de Lautréamont, The Songs of Maldoror: Definitely, classic from 1869 France. Don’t know much about him, though. Never read him.
  29. Fyodor Dostoevsky, Notes From Underground: A classic of course from Russia 1864. When I finish Crime and Punishment and The Brothers Karamazov. The only Dostoevsky I’ve read was 15 pages of The Brothers Karamazov. But those were some fine 15 pages!
  30. William Faulkner, Absalom, Absalom!: Sure, a classic, US, South 1931.
  31. William Faulkner, The Sound and The Fury: I should as it’s one of the greatest books ever, but it’s so intimidating, US South, 1929. Read the first page.
  32. Juan Filloy, Op Oloop: I really ought to, it’s a classic, out of Argentina 2009. Don’t know much about him other than being associated with the Oulipo School. Never read him.
  33. William Gaddis, J R: One of the greatest books ever, US, 1955. I need to but it’s so difficult! And 750 pages! Never read him.
  34. William Gaddis, The Recognitions: Another of the greatest books ever and just as hard as J R, US, 1975. 950 pages! See above.
  35. William Gass, Middle C: I really need to start reading him, but I hear he’s difficult. The short story I read by him (see above) was out of this world! US, 2013.
  36. William Gass, Omensetter’s Luck: Same. US, 1966.
  37. William Gass, The Tunnel: Same, except this one is one of his best. 650 pages! Supposed to be a classic, US, 1995.
  38. Gunter Grass, The Flounder: I should, his most famous work. 700 pages! Germany, 1977.
  39. H. D. (Hilda Doolittle), Helen in Egypt: A classic, US expat in Switzerland, 1961. I should but I’ve heard she’s hard as Hell to understand. Never read her.
  40. John Hawkes, The Lime Twig: Another classic, UK, 1961. Never read him, would be a good place to start.
  41. James Joyce, Ulysses: One of the top 10 greatest books of the last 200 years, Irish expat in Paris, 1921. Been meaning to forever, got 10-15 pages into it over a period of 40 years. Maybe it’s that 1,000 pages part? Need to get off my ass.
  42. Yasunari Kawabata, Beauty and Sadness: Possibly, Japan, 1975. I know nothing at all about this writer. Never read him.
  43. Clarice Lispector, Água Viva: I’ve never read her but I should, Brazil, 1973. I know almost nothing about her. Never read her and might be a good place to start.
  44. Clarice Lispector, Near to the Wild: Heart: See above, Brazil, 1943.
  45. Malcolm Lowry, Under the Volcano: Yes, classic story of alcoholism. US expat in Mexico, 1947! Never read him.
  46. Colman McCarthy, Blood Meridian: For sure! Terrifying but classic. US, 1985. Never read him.
  47. Joseph McElroy, A Smuggler’s Bible: He’s great but I’ve never read him and this might be a nice place to start. US, 1966.
  48. Nicholas Mosley, Impossible Object: He’s supposed to be great but I’ve never read him, and this might be a nice beginning. I don’t know him real well. UK, 1968.
  49. Harumi Murakami, 1Q84: Yes, it’s a classic, Japan, 2010! But 950 pages! Never read him.
  50. Harumi Murakami, Wind-Up Bird Chronicle: Definitely, another of his great books. 600 pages. Japan, 1995.
  51. Vladimir Nabakov, Ada, or Ardor: Of course, I love Nabokov, especially this, one of his finest. It’s hard to understand though! 625 pages! A major classic, Russian expat in US, 1969.
  52. Vladimir Nabakov, Invitation to a Beheading: Yes. Russian expat in France, 1936.
  53. Vladimir Nabakov, Lectures on Literature: Sure. Russian expat in US, 1980.
  54. Vladimir Nabakov, Pale Fire: For sure, once again, one of his most famous, but it’s supposed to be hard to figure out. A serious classic, Russian expat in US, 1959.
  55. Vladimir Nabakov, Pnin: Yes. Russian expat in US, 1955.
  56. Vladimir Nabakov, Speak, Memory: Yes. Various places, Russian expat in 1966.
  57. Flann O’Brien, At Swim-Two-Birds: Oh, yes, a little known classic, Ireland, 1939! He’s difficult, but he sounds fun, like Joyce. Never read him.
  58. George Perec, Life, a User’s Manual: A little known but great book, France, 1978. I know almost nothing about him except the association with the Oulipo Movement out of France. 650 pages! Never read him.
  59. Fernando Pessoa, The Book of Disquiet: One of the greatest books ever, 1935, Lisbon. Read bits and pieces, it’s intense! 550 pages. Never read him.
  60. Sylvia Plath, The Bell Jar: Really should, classic about mental illness, US, 1963. I’ve read some of her poetry, and it is out of this world!
  61. Marcel Proust, In Search of Lost Time: One of the top 10 books of the last 200 years, France, 1927. Why haven’t I read this yet? It’s only 3,200 pages. Slacker! Never read him.
  62. Thomas Pynchon, Against The Day: Absolutely, one of his best, US, 2006. But it’s 1,100 pages! I’ve read bits and pieces.
  63. Thomas Pynchon, Mason & Dixon: Of course, another of his finest, US, 1997. 875 pages! I’ve read a few bits of it.
  64. François Rabelais, Gargantua & Pantagruel: Definitely, it’s an old classic from 1556 France, sounds like a blast, but 1,100 pages! Never read him.
  65. Alain Robbe-Grillet, The Erasers: I should, as I am almost a Robbe-Grillet completist, France, 1950.
  66. Salman Rushdie, Midnight’s Children: A modern classic, Indian expat in the UK, 1981. It’s about his best so I really need to.
  67. Ernesto Sabato, The Tunnel: Little-known classic. Hear great things about it. Argentina, 1948. Never read him.
  68. Susan Sontag, Death Kit: Novel, sounds intense, US, 1967. Never read her.
  69. Susan Sontag, On Photography: Said to be a classic work, US, 1977. Maybe more interesting then the above.
  70. Susan Sontag, The Benefactor: This one is a novel, so it might be more accessible, US, 1963.
  71. Gilbert Sorrentino, Mulligan Stew: This is an absolute must, an obscure recent classic, US, 1979. Never read him.
  72. Lawrence Sterne, Tristram Shandy: A classic from UK 1759 but one of the greatest books of all time. Mandatory reading. 750 pages! Never read him.
  73. William Vollman, Argall: The True Story of Pocahontas and Captain John Smith: I probably should read any or all of these. He’s a bit difficult but not real hard, US, 2001. Part of the Seven Dreams series. Very good book, 750 pages!
  74. William Vollman, Europe Central: See above, US, 2005. Part of the Seven Dreams series. Won the National Book Award. But 850 pages!
  75. William Vollman, Fathers and Crows: See above, US, 1992. Part of the Seven Dreams series. Said to be excellent. 1,000 pages, though!
  76. William Vollman, Ice-Shirt: See above, US, 1990. Part of the Seven Dreams series. Good book.
  77. William Vollman, The Dying Grass: See above, US, 2015. Part of the Seven Dreams series. Excellent book, 1,400 pages, though!
  78. William Vollman, The Rainbow Stories: See above, US, 1989. Book about prostitutes. Good book.
  79. William Vollman, The Rifles: See above, US, 1994. Part of the Seven Dreams series. Very good book.
  80. William Vollman, The Royal Family: See above, US, 2000. Another book about prostitutes. Good book, but 800 pages!
  81. David Foster Wallace, Infinite Jest: I so need to do this, this is one of the top books of the modern era in the last 30 years, US, 2006. He’s hard but I can handle him. And then there’s the part about the book being 1,100 pages. Never read him.
  82. David Foster Wallace, The Broom of the System: Another modern classic, US, 1987. This one might be easier going.
  83. Virginia Woolf, Mrs. Dalloway: One of the greatest books of the last 200 years by one of the top ten greatest authors of the period and the only one that is a woman. But George Eliot might get on a list like that for Middlemarch. The all time classic, UK, 1925. Never read her.
  84. Virginia Woolf, Orlando: Classic, UK, 1928. Another mind-blower.
  85. Virginia Woolf, The Voyage Out: Another classic, UK, 1915. More great literature.
  86. Virginia Woolf, The Waves: Yet another classic, UK, 1931. Incredible writing.
  87. Virginia Woolf, To the Lighthouse: Another super-classic, UK, 1927.
  88. Marguerite Young, Miss Macintosh, My Darling: Modern classic, US, 1965, rather obscure, I have heard this is out of this world, except for the 1,200 pages! Never read her.

This is a list of another three of the books in the first list, but I have no particular interest in reading any of these at the moment. Since I made a point above about marking long books, these were three of those books that were particularly long.

Books From the List Above I Don’t  Particularly Want to Read and Why, Along with Background Information about Them

    1. Renata Adler, Pitch Dark: I know nothing whatsoever about this author or any of her books.
    2. Renata Adler, Speedboat
    3. Aeschylus, The Oresteia: No Greek plays. Why? I dunno!
    4. Apuleius, The Golden Ass See above.
    5. Aristotle, Poetics: No Greek philosophers, at least at the moment.
    6. Aristotle, The Art of Rhetoric: See above.
    7. Aristophanes, Lysistrata :No Greek  plays, though this one is a bit tempting.
    8. Margaret Atwood, Cat’s Eye: I like her prose and per poetry in small doses. She’s an incredible writer. Unfortunately, she’s also an typical feminist lunatic and typical feminist silliness and nonsense, a long with a dollop of the usual man-hating and evil male characters, mar her novels. Canada, 2000’s
    9. Marie Darrieussecq, My Phantom Husband: Well, I researched this author and I plan to break down and read Pig Tales, which sounds like quite a handful right there. First things first.
    10. Don DeLillo, The Body Artist: This is one his very early novels, I believe the 2nd. His early novels are generally considered to be inferior work to his later awesome novels like The Underground. Wow! US, 1980’s
    11. Rikki Ducornet, The Stain: She’s up my alley but I don’t know much about her or her books. Give me some time.
    12. Euripides, The Trojan Women (The Women of Troy): No Greek plays, except this one sounds tempting with the babes in the title. I’ll read any play if it’s about chicks!
    13. Euripides, Medea: Greek play. Not sure about this one.
    14. Fourier, Charles: The Social Destiny of Man: Or, Theory of the Four Movements. Frenchman, political scientist and philosopher, maybe an early socialist. France, 1840’s. I know next to nothing about the author and nothing about the book. 700 pages!
    15. Paula Fox, Desperate Characters: I know nothing whatsoever about this woman or her work.
    16. Sigmund Freud, The Uncanny: I’ve read a fair amount of his stuff and have some of his books lying around. He’s a much better writer than people think and he’s also a sort of universal genius or Renaissance Man. I’ve never heard of this essay though.
    17. Johann Wolfgang von Goethe: Faust I & II: The universal genius, but I’m tired of Faust stories. Germany, early 1800’s, 500 pages. I have an affinity for Elective Affinities though. Also the bildingsroman, Sorrows of Young Werther, and while we are at it, how about The Theory of Colors?
    18. E. T. A. Hoffman, The Life and Opinions of the Tomcat Murr: On the back burner with Richardson, DeFoe, Fielding. I do like Sterne and  Swift though – see above, so it’s not an anti-novelists of the  1700’s thing. But Sterne and Swift are wickedly, almost diabolicaly funny. The other three can be too, but another issue is their books are extremely long. Richardson’s Clarissa is one of the longest books ever written.
    19. Siri Hustvedt, The Blazing World: A modern writer. I have heard a bit about her, but know little about her or her work. Never heard of the book.
    20. Franz Kafka, Josephine the Singer, or The Mouse Folk: Let’s say I finish The Trial first, ok?
    21. Anna Kavan, Asylum Piece: I know nothing of this woman or her work. Never heard of the book.
    22. Anna Kavan, Ice: See above, never heard of this book either.
    23. David Mamet, Faustus: I’ve had enough of Faustus overload for the time being. You might say I have devil fatigue. I plan to spend a lot of time with the fucker later on though, so why add to me mystery by hanging out with him when I’m above ground?
    24. Thomas Mann, Doctor Faustus, or The Life of the German Composer Adrian Leverkühn, Told by a Friend: Germany, 1920’s. Once again, tired of Faust stories. Death in Venice does beckon over yonder hill though. Has for 40 years now. 550 pages.
    25. James Michener*, The Novel: Apparently a novel about writing a novel. Metafiction. Gets tiresome after a while, Barth is bad enough this way.
    26. Toni Morrison*, The Bluest Eye: I’m just sick and tired of her! I’ve already read three of her books. Yes they’re good but no, she’s not James Joyce or even Virginia Woolf. Hell, she’s not even Nora Zeale Thurston! Want a Black woman on the greatest list? Throw Houston on there! She’s as good as Eliot or Woolf. Their Eyes Were Watching God is truly out of this damned world! One of the greatest books ever written and it was written by a Black woman! The endless accolades about Morrison? Guess why? She’s Black! And she’s a woman! She’s an oppressed class times two, poor lass! I’m seeing a lot of 10 greatest books ever with her next to Tolstoy, Melville, Joyce, Eliot, Dostoevsky, and even Virginia Woolf, whose To the Lighthouse barely makes it to 10th place. Now we throw Morrison in with these illustrious gods? I don’t think so. Just get out. I guess affirmative action has come for the great book lists too. Sigh.
    27. Sylvia Plath, The Bell Jar: A book about a nutty woman thrown into a mental hospital because she’s crazy and suicidal. Written by a crazy and suicidal woman who eventually killed herself. I guess the book was a premonition. Hard pass. But her poetry though! Read her poetry! Some of the best ever written!
    28. Dorothy Richardson, Pilgrimage, Vol. 1: Pointed Roofs: I don’t know much about her or her famous series of books, The Pilgrimage.
    29. Sophocles, Antigone: Greek play. Nuff said.
    30. Sophocles, Oedipus the King: This one is a bit tempting though. I’m a total sick fuck and all the Mommy fucking and Daddy murdering has got me real interested, I must say!
    31. Sophocles, Electra: Greek play again. Yawn. This one’s about a babe though, so my other head says yes, read it.
    32. Enrique Vila-Matas, Dublinesque: Know nothing about the writer and never heard of the book.
    33. Edmund White, The Flaneur: A Stroll through the Paradoxes of Paris: Book is set in Paris. Author is an American gay man. And he’s gay with a capital G. Gay as a rainbow. Times 1,000. A coterie of young gay men are all fucking each other and falling in love with each other. They’re all Adonises (obviously). All young gay men in gay fiction are named Adonis. Anyway, that’s the plot. Gross.  Now get ready because I’m about to become a total asshole here. This is a fag book! Well, it is. His books are about gay men, often young ones, who are falling in love with other hot young gay men, with lots of jolly buttfucking to pass the time. He is said to be an awesome writer though. And I did plow through William S. Burroughs’ books, and they’re practically out and out gay pornography, dudes fucking dudes all the way through his books. Thinking back, I don’t know I do this. Hey gay writers! Pro tip! Quit writing about male homosexuality and maybe some of us straight guys will read your stuff. In the meantime, you’ve all locked yourself into a ghetto, or better yet, a prison. But there’s plenty of hot sex when you’re behind gay bars in the prison system, so don’t fret!
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10 thoughts on “139 Great Difficult Books to Crack Your Brain”

  1. No sci-fi? Genuine question- aren’t science fiction books revered? None from Jules Verne, HG Wells, Isaac Asimov- there must be some novel

    1. Haruki Murakami’s 1084 has sci-fi elements. John Barth’s fabulist Giles Goat-Boy could be seen as sci-fi. Is Philip Roth’s The Breast sci-fi? One could surely make the same case for Pig Tales. Both resemble Kafka’s Metamorphosis. Is that sci-fi? And let’s face it – is Swift’s Gulliver’s Tales not proto-science fiction? It has sci-fi elements for sure.

      None from Jules Verne, HG Wells, Isaac Asimov- there must be some novel

      This was just a list I got from some Goodreads group. There were specifically looking for difficult, brain-fry books, hence the name Brain Pain. I don’t think any of the books by those three are all that difficult, especially the first one.

      It was up to them whether to put sci-fi stuff on there. To me, there are definitely some brain-fry sci-fi books out there. Neal Stephenson’s stuff and Samuel R. Delany’s Dahlgren are two that come to men.

      1. I’m curious if you’ve read Book of the New Sun, I’ve heard it’s among the most literary science-fiction published.

  2. The Ancient Engineers (L. Sprague DeCamp)
    Animal Farm (George Orwell)
    The Crowd* (Gustave LeBon)
    *Definitely in my top ten of the greatest books of the last 150 years.

      1. Yep. 1895 (English translation from the original French, written 1893). French psychiatrist that demonstrated how crowds (lynch mob-type human behavior) manifests itself in “crowds” as opposed to encountering individuals in a state of isolation. His basic point? “Crowds don’t reason, they lynch.”

        1. Yes I rememeber the name now. He’s the father of modern Sociology. Of course Weber and Thurston Weblein wrote their great books in the next 20 years or so.

  3. Off the top of my head, the only ones from the list I’ve read are 1Q84, the Waste Land, Lolita, Pale Fire, Ulysses, and Gargantua & Pantagruel. Of the ones I haven’t read but would like to read someday, I haven’t gotten around to reading more of Borges beyond Labyrinths and I haven’t read much Pynchon yet because I’m genuinely intimidated by the sheer reported depth of his works. Surprised that there’s no Herman Melville on the list because The Confidence-Man and his poetry are fantastic, though I haven’t read Moby Dick yet.

    Re: Gargantua & Pantagruel, it’s a fairly episodic novel and the chapters are short, so I think you’d enjoy it even if you only read a few chapters every so often.

    1. 1Q84, Pale Fire, Ulysses, and Gargantua & Pantagruel

      What did you think of those four in terms of length, difficulty, interest, achievement, and the general reading experience. I’m especially interested in the three other than Ulysses. I’ve definitely been wanting to read Pale Fire for a long time. How does it compare with Lolita?

      though I haven’t read Moby Dick yet

      Just pick it up and start reading. It goes a lot faster than you think, and it doesn’t really matter if you understand everything or not.

      I haven’t read much Pynchon yet because I’m genuinely intimidated by the sheer reported depth of his works

      The Crying of Lot 49 is the easiest one to start out with. V. is a good read even though you might not really understand what’s going on. Vineland is quite a breeze to read, as are the early pieces in Slow Learner. The two most recent books, Inherent Vice and Bleeding Edge, are among the easiest reads in his canon. In fact, some people dislike them along with Vineland for that very reason – they’re supposedly too lightweight.

      Gravity’s Rainbow is the heavyweight and a lot of people are scared of it, but it’s such a fun book to read that it doesn’t really matter if you understand what’s going on or not. It’s one of those books that’s a blast even if you can’t figure out what the Hell is going on half the time. Go ahead and start in on it. It’s such a blast to read it!

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