The idea for this puzzle came to me while I was singing in the shower one morning before work. This Aretha Franklin song had been on the radio when I woke up, and stuck around in my head. I played around with the approach a little, and decided that for "Chain, chain, chain" I would need to have three chains. I played around at first with having all three chains be based on the definition of fool as a stupid person, but rejected that when I realized that the grid would just be full of insults. Instead, I went with the approach of having a slightly different meaning of "fool" for each theme entry: stupid person (noun) / trick (verb) / jester (noun). I actually tried to see if there were enough named jokers in literature and history to make a good 17-letter/15-letter chain, but I was unable to find enough that worked to do so.
The clue for TYPO came about when I was reviewing a writing assignment that one of my daughters had in grade school. The pirate character said "eye, matey," and I had to explain that was not how that term was spelled. She said that she thought it had something to do with the eye patch that pirates stereotypically wear. I guess thatofficially it was not a typo, since she did indeed mean "eye," but the eye/aye combination struck me as usable in place of "tit for tat."
GB adds: What a delightful puzzle! ... and now I can't get that tune out of my head. David's clues tend towards the hard side, and I had to soften up a few of them, but there was lots of really good stuff and I certainly learned quite a bit. Our beta testers were blown away by the SRO clue, with its play on the play [Jonathan Larson musical that was loosely based on Puccini's "La Boheme"]. "Rent" played on Broadway (and other theatrical venues) to "standing room only" crowds," but David's clue also alludes to "single room occupancy" that might be the case for some rentable living (should we say barely liveable?) quarters. David shared this puzzle too late for me to post it on April Fools' Day (for which we anyhow had planned to go with something else), but keeping in mind his clue for POLE, it is a real pleasure to release it on May Day.
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