Musical riddles in a world after LLMs

1 July 2026

Is it still possible to write riddles or quiz questions that are satisfying for humans to answer, but difficult for LLMs? A couple of months ago I tried this on Bluesky, an attempt which went entirely ignored. The obvious explanation is that I'm a bad riddle-writer but I still think the concept is kind of fun so I'm going to reproduce them here for posterity.

Question 1:

What song begins with the words “director of public”?

Question 2:

If you take four and one, you get which acclaimed track with a 4/4 time signature?

Question 3:

In which song does the singer go further than 180° but less than 360°?

I went to a certain amount of effort testing these against chatbots of the time and they were struggling to get it without hints. What do you think? How easy do you find these? Can you come up with any good ones? Drop me an email!

Tom's Opinions Blog by Thomas Karpiniec
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