WilbaW
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Wilba's Dissonant Compositions
Interesting challenge Jim. I get the sense from your words and images that you're interested in deliberate juxtapositions and incongruities, rather than just things that look odd. Let's see if I'm on the right track...
No Standing
This is a scan of a small print from my 35mm SLR days in the early 1980s. I found the shoe in the street when I was wandering around with the camera. As I tried to find an interesting way to frame it, suddenly the words "NO STANDING" appeared in the viewfinder. I laughed out loud when I realised what meaning I could make with that, like, the guy was standing there minding his own business, and was grabbed so fast by the No Standing Police that his shoe came off. (BTW, "NO STANDING" means it's a clearway, you're not allowed to stop a car there.)
Hamish
I did this one for a "through glass" challenge on another forum. I like the way it makes someone with the mentality of a five-year-old boy look like a learned adult.
Kelvingrove Student (Cameronians War Memorial (1924), Glasgow, Scotland)
I didn't think too much about this shot at the time, I just thought it looked interesting, but the more I look at it the more I see it as a contrast between life for young people now and in the past. Here's this spotty nerk doing his homework on the way to his first lecture of the day, whereas a century ago he might have been leaping out of a trench into a hail of bullets and mortar.
Big Tank
And one for the fun of it. I don't think this one quite fits what you're asking for, but I wanted to share it for the Escher-like quality it has, both in the challenge of disentangling the staircase from its shadow, and the momentary uncertainty about whether we're looking at a convex or concave surface.