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The Question: What's Your Favorite Riddle?

By James Guttman, James Bullock, and Dan Crocker Jun 29, 2016 - 1:53 PM print


It's time for another edition of "The Question" - We Want Insanity's weekly answer to something we all have our own opinion on. See what we have to say and then share your own. That's what questions like this are for...

What’s Your Favorite Riddle?

James Guttman:

I will never forget this one. It bugged me out at the time and even after you figure out the reason behind it, it’s still perplexing. Here goes:

Three men go to a hotel to rent a room. The front desk attendant tells the three men that the room will be $30. Each man pays $10 – adding up to 30 – and heads up to bed or whatever it is these three men are going to do up there in a $30 a night room. Sketchy.

Once they’re gone, the front desk attendant realizes that he overcharged them. The room is only $25 for the night. So he calls over the bellhop (if that’s still what we call them) and tells him, “Here. Take these 5 dollar bills up to the room and give those three guys back the money they’re owed.” He obliges.

On the way up to the room, the bellhop thinks to himself, “These guys can’t split $5 evenly. What I’ll do is keep $2 for myself and give each man back $1. Then we’ll be square.” That’s what he does.

So let’s work it out. Each man gets back $1. So they each have now paid $9 for the room. 9 x $3 = $27. The bellhop kept $2. $2 + $27 = $29.

Where’s the other dollar?

Yeah. Chew on that one for a while.



James Bullock:

As much as I would love to use the first riddle I knowingly learned courtesy of “The Muppet Babies” (“What’s black, white and red all over?”), I just can’t because as the years progress and one of my favorite childhood shows ran its criminally short course I discovered the world was brimming with great riddles. For some reason number-based brain teasers the ones that have intrigued me the most including my favorite that had me stumped for a long time when I was young: “1, 11, 21, 1211, 111221, 312211, 13112221 What comes next?”

You’ll probably figure it out faster than I did – not having the feeling like you were suffering from “The Simpson Gene” and had to look forward to a life of stupidity and underachievement.


Dan Crocker:

I'll be honest. I'm not a big fan of riddles. Maybe it's because over the years so many students have written papers or stories or poems like they're writing a riddle. Example: My hands move slowly but never . . .” Me: Just call it a clock. It's a clock! That's why we have that word, so you can call a clock a clock.


I do like this these though:




I'm a big fan of jokes, and some of those are like riddles. Here is my favorite one.


Q: How do you get a witch pregnant?
A: You f*ck her.




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