All of the following are modernized retellings of the classic book/movie listed in the comment. (Holy crap this was my 300th list!)
  1. β€’
    My Own Private Idaho
    William Shakespeare's "Henriad" plays
  2. β€’
    A Thousand Acres by Jane Smiley
    Shakespeare's King Lear
  3. β€’
    Omeros by Derek Walcott
    A sort of Caribbean Homer's Odyssey
  4. β€’
    Bridget Jones's Diary by Helen Fielding
    Jane Austen's Pride and Prejudice
  5. β€’
    The Stars My Destination by Alfred Bester
    Alexandre Dumas's The Count of Monte Cristo
  6. β€’
    Ulysses by James Joyce
    Homer's The Odyssey
  7. β€’
    The Magnificent Seven
    Seven Samurai
  8. β€’
    O Brother, Where Art Thou?
    Homer's The Odyssey. Again.
  9. β€’
    The Wiz
    The Wizard of Oz but in Harlem
  10. β€’
    West Side Story
    Shakespeare's Romeo and Juliet but on the Upper West Side
  11. β€’
    The Lion King
    Shakespeare's Hamlet
  12. β€’
    Ran by Kurosawa
    Shakespeare's King Lear
  13. β€’
    10 Things I Hate About You
    Shakespeare's The Taming of the Shrew
  14. β€’
    Jane Austen's Emma
  15. β€’
    Charles Dickens's A Christmas Carol
  16. β€’
    Apocalypse Now
    Joseph Conrad's A Heart of Darkness
  17. β€’
    Edmond Rostand's Cyreno de Bergerac
  18. β€’
    1Q84 by Haruki Murakami
    George Orwell's Nineteen Eight-Four (but in Tokyo!)
  19. β€’
    J. M. Barrie's Peter Pan
  20. β€’
    The Bible's Gospel of Matthew (and Luke)
  21. β€’
    Rosencrantz and Guildenstern Are Dead by Tom Stoppard
    Shakespeare's Hamlet
  22. β€’
    The Story of Edgar Sawtelle by David Wroblewski
    Shakespeare's Hamlet
  23. β€’
    On Beauty by Zadie Smith
    E. M. Forster's Howard's End
  24. β€’
    The Penelopiad by Margaret Atwood
    Homer's The Odyssey
  25. β€’
    A. I.
    The Adventures of Pinocchio by Carlo Collodi
  26. β€’
    Hans Christian Andersen's The Snow Queen
  27. β€’
    The Hours by Michael Cunningham
    Mrs Dalloway by Virginia Woolf
  28. β€’
    Sleeping Beauty by Charles Perrault
  29. β€’
    La Bohème by Giacomo Puccini
  30. β€’
    Brazil by John Updike
    Tristan and Iseult/Isolde
  31. β€’
    Dorian, an Imitation by Will Self
    The Picture of Dorian Gray by Oscar Wilde
  32. β€’
    Kiss Me, Kate
    Shakespeare's The Taming of the Shrew
  33. β€’
    My Fair Lady
    Pygmalion by George Bernard Shaw
  34. β€’
    Barb Wire
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    Casablanca (really!).
    Suggested by @fisackerly
  35. β€’
    Running Scared (2006)
    Through the Looking Glass. Underrated film... The Mad Hatter is a pimp!
    Suggested by @eliolsberg
  36. β€’
    Cruel Intentions
    Christopher Hampton's play Les liaisons dangereuses
    Suggested by @jennienina
  37. β€’
    Men of Respect (1990)
    Shakespeare's Macbeth
    Suggested by @allie