4 Bonkers Puzzle Contests That Baffled The World

4  Cain's Jawbone -- The Murder Mystery Only a Handful of People Have Solved in Nearly 100 Years

Ah, 1934, the year Judi Dench was born, Donald Duck made his screen debut, and cryptic crossword writer Edward Mathers (who used the pseudonym "Torquemada") released a book of puzzles, presumably to kill time until World War II finally rolled around. The last 100 pages of the book formed a complete mystery novella entitled Cain's Jawbone -- but the pages, not unlike a McDonald's ice cream machine, were out of order. 

To solve the puzzle, readers had to rearrange the pages into the correct sequence and also solve the six murders contained in the story. This was no small feat; not only is the prose composed of coded wordplay forming "largely incomprehensible … meandering sentences," but there are more than 32 million possible combinations of pages. The prize for this near-insurmountable task was 25 pounds (which went much further in '34 than today), and it was claimed by just two people.

After falling out of print for the better part of a century, just last year, a new edition of Cain's Jawbone was released thanks to a crowdfunding campaign. While Torquemada is obviously quite dead, the long-lost solution was pieced together by Shandy Hall curator Patrick Wildgust, and the publisher offered a £1000 prize to any reader who could decipher it.

British comedy writer John Finnemore became just the third person in history to claim a prize for solving Cain's Jawbone, proving once and for all that "comedy writer" is the most intelligent of all professions. According to Finnemore, it took him four months to figure it all out, which he was only able to do thanks to both the internet and being forced to stay indoors for months on end due to lockdowns because apparently, he wasn't quite up to the challenge of binge-watching Tiger King while eating raw cookie dough.

3 MAZE -- No One Could Even Figure Out the Riddle They Were Supposed to Answer

Whether you're using worn-down crayons on a children's placemat or fleeing your possessed ax-wielding father in the dead of winter, mazes can be a whole lot of fun. One of the best mazes around, oddly enough, comes in the form of a picture book, MAZE: Solve the World's Most Challenging Puzzle, written and illustrated by Christopher Manson, AKA the best C. Manson around.

The premise of the book is simple; you're guided by an unnamed narrator through a mysterious building. Each room leads to several other numbered rooms that correspond to that page number, which you then turn to -- kind of like a Choose Your Own Adventure, except there's less of a chance that it will strand you on a planet populated by elderly babies. To chart the correct path, one has to pick a certain door, which requires interpreting cryptic clues hidden in each illustration.

While not Manson's original intention, the publisher of MAZE (originally titled Labyrinth but later changed to avoid the legal wrath of Jim Henson) decided to make the whole thing a contest: whoever could solve it would get $10,000 -- which we're pretty sure could pay for a luxury car powered by New Coke back in the '80s. To win, you had to map out the "shortest path" to the center of the maze and back, plus a hidden riddle "exactly as indicated by the clues in the book" and its solution. This proved to be ridiculously hard. When the contest ended, nobody was "even close to a solution." So the publisher had to delay the contest deadline twice and even sent contestants some extra clues.

Eventually, the prize money was split between 10 people who had figured out how to navigate the maze but had no friggin' clue what the answer to the riddle, or even the riddle itself, was. While the publisher eventually revealed the answers, the book is so dense that people are still analyzing and debating its contents. This includes the identity of the guide and the possibility that the secret riddle is actually part of yet another, larger riddle offering some kind of ultimate "lesson" to the reader. Fans have also created elaborate graphs mapping out the maze, which we'd warn you is a spoiler if it weren't as impenetrable as a vibranium condom. 

There's even a YouTube channel dedicated to solving all of its mysteries -- which, again, in no way involve David Bowie's junk. 

2 Treasure Quest -- A Million Dollar Prize May or May Not Have Gone to a Real Person

In the 1990s, CD-ROM computer games were all the rage, whether it was Myst, or The 7th Guest, or Pyst, the Myst parody featuring a hot-tubbing John Goodman that somehow actually happened. Then in 1996 came Treasure Quest, in which players had to solve an elaborate mystery left behind by a dead college professor that could only be gleaned by wandering around his virtual mansion. In each room, you'd encounter A) some janky computer graphics and B) Star Trek: Deep Space Nine's Terry Farrell in one of many costumes seemingly stolen from a dinner theatre production of The Mousetrap.

Within the world of the game "Prof. Faulkner" has left $1 million in his will to whichever of his students is able to solve the mystery. But what really got people's attention wasn't the story or even Lt. Dax's wig collection, but the fact that the player first to figure out the solution would win one million, honest-to-goodness real-world dollars. The game was so hyped, and security so tight, that no review copies were sent to the press and retailers weren't allowed to sell the game until "12:14 a.m." on a certain day -- which the game makers claimed might "be the first clues players need in order to solve the mystery."

The intensely difficult puzzle was eventually solved by a guy named Paul Wigowsky, who somehow deduced that the mansion and its interconnecting rooms formed the 22 paths of the Tree of Life which he had seen in books about Kabbalah.

But he … didn't get the prize money. According to the company behind Treasure Quest, Sirius, Wigowsky didn't put his "contest registration number in the appropriate place" and was therefore disqualified. If that sounds fishy, this next part of the story is a veritable Red Lobster buffet. The actual contest winner, according to Sirius, was a San Francisco resident named P. Dreizen -- but this person was never seen or heard from, and fans of the game became suspicious. 

Sirius claimed that they didn't make a big deal about the contest winner because they were in the process of abandoning CD-ROM games and getting into the business of CD-ROM movies, which could be viewed on your computer (soon to be rendered obsolete by DVD). Sirius also reduced their staff by two-thirds and decided to move out of their office building and into a warehouse, which is never a good sign. Adding to speculation that this company, which was clearly running out of money, might have made up a fake contest winner to avoid paying the million bucks, the name "P. Dreizen" turned out to be an anagram for "End Prize." 

As entertaining as Star Wars and prolonged gas shortages might be, people in the late '70s were super-psyched about a hot new trend: armchair treasure hunts. It began with the 1979 book Masquerade, which purported to contain hidden clues leading to a real-life buried treasure: a "golden hare." People flocked to England from all over the world in search of the treasure, and it wasn't until 1982 when someone finally unearthed the prize.

Sadly, the hunt ultimately ended in scandal just a few years later, after a newspaper investigation discovered that the winner was secretly fed information by the author's ex-girlfriend. But before that unfortunate revelation, the success of Masquerade spawned a slew of imitators, perhaps the most well-known today is a 1982 book called The Secret by Byron Preiss. To help promote his book of fantasy stories, Preiss also included a treasure hunt component in the book. This time, there were twelve treasures to be found, buried in twelve unidentified cities across North America.

The treasure itself was one of twelve precious gems held by the author, which he would offer up in exchange for one of the ceramic keys that were enclosed in the hidden treasure boxes, or "casques," seemingly made out of jelly beans and mayonnaise.

Finding the treasure involved matching a "cryptic verse" with one of 12 paintings -- but the book doesn't tell you which verse goes with which painting. 

Somehow making things extra confusing, the book didn't even specify which cities contained casques, leaving readers with near-endless possibilities. After a year, no one had found a single casque, that is until three teenagers managed to find one in Chicago's Grant Park after six months of digging.

Because the clues were so obtuse, the next casque wasn't found until 2004 -- and remember, this was supposed to have been a marketing stunt to generate publicity for the book, which had already come and gone by that point. Now, despite the fact that Preiss died tragically in 2005, people are still hunting for the casques, and obsession with the puzzles has only intensified thanks to internet forums, podcasts, and an episode of the Discovery Channel's Expedition Unknown. Amazingly, in a 2019 follow-up episode, a Boston man actually discovered a third (slightly smashed-to-pieces) casque in a Boston ballpark and was awarded the corresponding gem by Preiss' widow.

Things have gotten so intense in recent years that, back in 2019, a French Secret fan claimed to have found the San Francisco casque, which turned out to be a shockingly unconvincing fake.

By the way, each of these gems is only worth around $1000, so not exactly One-Eyed Willy's pirate ship full of gold. Still, it would be amazing if more casques are found, even if it means grabbing a shovel and desecrating your neighbor's yard right this very moment.

You (yes, you) should follow JM on Twitter! 

Top Image: Bantam Books/Unbound