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Puzzling Books: 13 Books Offering Intriguing Enigmatic Mysteries

By Ashly Moore Sheldon • December 05, 2021

First published in 1934, Cain's Jawbone is a fiendishly difficult literary puzzle that has only ever been solved by four people. Last week, the title suddenly became a hot commodity when a popular TikTok user began charting her own attempt to crack the case, which involves reordering the 100 pages of the scrambled murder mystery to determine whodunnit. The book is currently sold out, but here are some similar possibilities to consider.

Interactive Enigmas

For fans of Agatha Christie, Arthur Conan Doyle, and Edward Gorey, Murder Most Puzzling: 20 Mysterious Cases to Solve invites readers to play detective and solve a series of absorbing, murder-mystery-themed puzzles. This collection of darkly humorous puzzles by Steph Von Reiswitz offers a whirlwind adventure, laced with humor and a dash of the macabre.

Some other books that offer the reader an opportunity to take on the role of sleuth include:

For all book-loving puzzle solvers or puzzle-loving book readers, pick up The Literary Pocket Puzzle Book: 120 Classic Conundrums for Book Lovers. This handy, portable pocket-sized book by Neil Somerville features a variety of puzzles that will exercise your knowledge on such greats as Shakespeare, Mark Twain, Marcel Proust, Henry James, and more.

And for those more inclined to solve math mysteries, try The Moscow Puzzles by Boris A. Kordemsky. Jam-packed with 359 marvelously varied puzzles ranging in difficulty level, the popular Russian puzzle book is lavishly illustrated with clear diagrams and amusing sketches.

For true antiquity, try this reissued copy of the centuries-old The Voynich Manuscript, with essays exploring what has been discovered about the book. Written in an unknown script by an unknown author, the beguiling volume's strange language and elaborate illustrations remain as baffling as they are beautiful.

More Mysterious and Strange Reads

Many readers may prefer a more passive experience when it comes to puzzling plots. Sometimes all we really want to do to crack the case is just turn the page. These books offer the experience of riding along on a mind-twisting tale.

  • Gnomon by Nick Harkaway: a virtuosic novel set in a near-future, high-tech surveillance state, that is equal parts dark comedy, gripping detective story, and mind-bending philosophical puzzle.
  • The Westing Game by Ellen Raskin: This puzzle-knotted, word-twisting, Newbery Medal winner involves sixteen people invited to the reading of Samuel W. Westing's will. They could become millionaires, depending on how well they play the game.
  • Midnight at the Bright Ideas Bookstore by Matthew J. Sullivan: Bookstore clerk Lydia Smith has spent her life hiding in plain sight, but when a bookstore patron commits suicide and leaves her all of his possessions (plus a baffling mystery), her meticulous existence comes unglued.
  • The Raw Shark Texts by Steven Hall: Eric Sanderson wakes up in an unfamiliar house with no memory of former life. All he has are diary entries recalling Clio, his perfect love who died mysteriously. He embarks on an edge-of-your-seat journey to uncover the truth.
  • S. by Doug Dorst and J.J. Abrams: One book. Two readers. A world of mystery, menace, and desire. The chronicle of two readers finding each other, and their deadly struggle with forces beyond their understanding.
  • Mr. Penumbra's 24-Hour Bookstore by Robin Sloan: The recession has shuffled Clay from work as a web designer to the employ of an odd bookseller. And pretty quickly, Clay discovers that this store is even more curious than he initially thought.

If you're someone who loves to solve mysteries, or even just read about others solving them, you may find something to love here in these perplexing titles. Let us know if you have any to add to the list.

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Read more by Ashly Moore Sheldon

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