Riddles take on an interesting and important role in the Dark Tower Series, especially in "The Waste Lands" and "Wizard and Glass". The intro to "Riddle-De-Dum", one of two books Jake Chambers brings from his when/where into Mid-World, says "Riddles are perhaps the oldest of all the games people still play today. The gods and goddesses of Greek myth teased each other with riddles, and they were employed as teaching tools in ancient Rome. The bible contains several good riddles." To Gunslingers riddling is very serious business and nothing like a joke. Having to study riddles as part of their schooling they gain a great respect for the quality it takes to make truly great conundrums. Eddie Dean believes jokes to be a form of riddling, which Roland refuses to acknowledge; "It is senseless and unsolvable, and that's what makes it silly. A good riddle is neither." However, he is forced to change his opinion during the riddling contest against Blaine the Mono when it is Eddie's jokes which allow them to win.
Riddles are said to have been invented by Bessa to entertain her husband Gan and were loved by the Queen O'Green Days. It is said riddles done during the Fair Days of Wide Earth wake her from her Winter slumber.
Riddling in Gilead
Riddles were a very serious business in Gilead. During the seven Fair Days there were always riddling competitions, with the Fair Day of Wide Earth and Full Earth being the most important. These were the most important times because the riddles were suppose to foretell well or ill for the success of the crops.
Abel Vannay made sure his young gunslinger students studied riddles and took them very seriously, believing "a boy who could answer a riddle was a boy who could think around corners." Vannay would hold a competition once a week and the winner was rewarded by being allowed to go home early for the day.
Roland is open that during this time he enjoyed riddling but was never very good at it,unlike his ka-mate Alain and his other teacher Cort, since he lacked the imagination needed and was kind of slow. Cort was the finest riddler of Gilead and was often the one to take home the Fair-Day goose. Roland acknowledged this by saying "He'd forgotten more riddles than the rest of us ever knew, and after Fair-Day Riddling Cort always carried home the goose." Cort was very serious about riddles, like the rest of Gilead, and once he killed a man who had tried to cheat him.
Fair Day Competitions
"Let those who seek to match wits with our riddle master step forward! Face a challenge that no bullet may vanquish but instead must be met men of high enough caliber!"
At midday on a Fair Day a great barrel was placed in the center of The Hall of the Grandfathers, the only day when the hall was opened to the common folk of Gilead. Riddles were then thrown into the barrel on bark scrolls. New riddles were added every year but most of the riddles were extremely ancient. Three judges, one of which was always a Gunslinger would then examine them and if they were deemed fair then they would be allowed in the competition.
Participants, men and women, then drew lots to find where they were in the riddling line and once they had taken their place in the line the competition would begin. The competition would start with the first contestant in line drawing a riddle from the barrel. In turn they would give the bark scroll to the Master of the competition who would ask the riddle. A three minute sand timer would then be started and if they could not answer the riddle, or if they guessed wrong, it was passed to the next contestant and they are disqualified. The eventual winner was awarded the largest goose in the Barony of Gilead.
People take the competition seriously and have been known to break out into arguments and fist fights, it is taken so seriously as they believe the winner gains favor in the eyes of Bessa. Cort proved this when he went against Kingson, at the time posing as traveling acrobat and singer. Kingson had stolen Vannay's book of riddles and replaced the answers with his own. Cort discovered this and killed the man.
- The riddle that lead to the discovering of the cheater was: "Not chest or box is now discussed. Money can be held in it, but just as we test its metal, within it there is rust." Kingson answered "A treasure sack" when the correct answer is "trust", a play on the word "mettle".
Jake the "Hyperborean Wanderer"
As Jake deals with being split in half, "I died" "No you didn't", he writes an essay for his english class called "My Understanding of Truth." in which he includes three riddles that are seen multiple times afterwards:
- When is a door not a door? When it is a jar.
- What has four wheels and flies? A garbage truck.
- What is black and white and red all over? A blushing zebra.
Jake takes "french leave" from school when he realizes he did not write the essay, and the voices in his head grow louder, and starts to wander New York. It is during this wandering that Jake finds the Vacant Lot, but not before he stumbles into The Manhattan Restaurant of the Mind, a very important bookshop owned by Calvin Tower. In the store Jake buys "Charlie the Choo-Choo" and Tower gives him "Riddle-De-Dum! Brain-Twisters and Puzzles for Everyone!" The first riddle Jakes sees when he opens "Riddle-De-Dum" is "When is a door not a door?" just like in his mysterious essay. As he leaves he reads the intro to the book and comes across another riddle, famously from the Bible that Samson had told on the day he married Delilah.
"Out of the eater came forth meat,
and out of the strong came forth sweetness!"
Since Jake does not have the answer section of the book he turns around to see if Tower or his friend have the answer. Aaron Deepneau has the answer but instead of giving it directly to Jake he sings it for him.
"Samson and a lion in attack,
And Samson climb up on the lion's back.
Well, you've read about lion killing men their paws,
But Samson put his hands round the lion's jaws!
He rode that lion 'til the beast fell dead,
And all the bees made honey in the lion's head."
Deepneau tells Jake the riddle is a double so it has two answers, both "lion" and "honey." Before Jake leaves the book store for the Vacant Lot and it's Rose Deepneau gives Jack another riddle, but does not give him the answer.
"What can run but never walks,
Has a mouth but never talks,
Has a bed but never sleeps,
Has a head but never weeps?"
Later that night Jake gets the answer to the riddle, "a river," when a young boy version of Eddie visited him in a dream.
The Road to Lud
Shortly after leaving River Crossing towards Lud Roland tells the ka-tet of his exeprience with riddles when he was still a young gunslinger. He teaches them about the serious nature his people placed on riddles, the Fair Day Riddling contests, and cuts Eddie down for making jokes and calling them riddles. Eddie tries to argues that his "silly" riddles are suppose to be that way to make people laugh, but when he sees Roland is just getting offended he drops the subject knowing that the gunslinger will not see it his way.
- Roland: What's dressed when night falls and undressed when day breaks? A fire.
- Roland tells this one to Jake as he tries to light a campfire for the first time.
- Eddie: Why did the dead baby cross the road? Because it was stapled to the chicken.
- Eddie: What's green, weighs a hundred tons, and lives at the bottom of the ocean? Moby Snot, the Great Green Whale
- Jake shares the one Deepneau told him but did not give the answer for. Roland was able to guess the answer as "a river."
- Roland: "What lies in a bed, and stands in bed?/ First white, then red/ The plumper it gets/ The better the old woman likes it?" Wenberry(Mid-World)/Strawberry(Keystone World)
- Eddie guesses "dork" but is shot down by Roland
- Eddies asks "When is a door not a door?" again and tricks Roland and Susannah.
- Jake: "There is a thing that nothing is, and yet it has a name. It's sometimes tall and sometimes short, joins our talks, joins our sport, and plays at every game."
- Jake asks this one from "Riddle-De-Dum" so he does not know the answer. No one in the ka-tet can guess it, but of course Blaine could. The answer is "a shadow."